CN110627626A - Preparation method of propargyl acetone compound - Google Patents
Preparation method of propargyl acetone compound Download PDFInfo
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- CN110627626A CN110627626A CN201911015223.4A CN201911015223A CN110627626A CN 110627626 A CN110627626 A CN 110627626A CN 201911015223 A CN201911015223 A CN 201911015223A CN 110627626 A CN110627626 A CN 110627626A
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- Prior art keywords
- propargyl
- propargyl alcohol
- acetone
- compound
- acetonitrile
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- 238000002360 preparation method Methods 0.000 title abstract description 6
- -1 propargyl acetone compound Chemical class 0.000 title description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical class OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 11
- HRADVHZVMOMEPU-UHFFFAOYSA-N 3-iodopyrrolidine-2,5-dione Chemical compound IC1CC(=O)NC1=O HRADVHZVMOMEPU-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- ACANPLUGNKZWRO-UHFFFAOYSA-N C(C#C)CC([CH2-])=O Chemical compound C(C#C)CC([CH2-])=O ACANPLUGNKZWRO-UHFFFAOYSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- MQVQPQJPNZJTAY-UHFFFAOYSA-N hex-5-yn-2-one Chemical class CC(=O)CCC#C MQVQPQJPNZJTAY-UHFFFAOYSA-N 0.000 abstract description 8
- 230000003647 oxidation Effects 0.000 abstract description 7
- 230000001590 oxidative effect Effects 0.000 abstract description 7
- 239000007800 oxidant agent Substances 0.000 abstract description 5
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 239000000047 product Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- LNPIRLQEFJBWMD-UHFFFAOYSA-N 1-naphthalen-2-yl-3-phenylprop-2-yn-1-ol Chemical compound C=1C=C2C=CC=CC2=CC=1C(O)C#CC1=CC=CC=C1 LNPIRLQEFJBWMD-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VSYZTLDXUSITBI-UHFFFAOYSA-N 1-(4-bromophenyl)-3-phenylprop-2-yn-1-ol Chemical compound C=1C=C(Br)C=CC=1C(O)C#CC1=CC=CC=C1 VSYZTLDXUSITBI-UHFFFAOYSA-N 0.000 description 1
- PIMAGHUGARRUIS-UHFFFAOYSA-N 1-(4-bromophenyl)-3-phenylprop-2-yn-1-one Chemical compound C1=CC(Br)=CC=C1C(=O)C#CC1=CC=CC=C1 PIMAGHUGARRUIS-UHFFFAOYSA-N 0.000 description 1
- ZALJRTWXVJZKEX-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-phenylprop-2-yn-1-ol Chemical compound C=1C=CC=CC=1C(O)C#CC1=CC=C(Cl)C=C1 ZALJRTWXVJZKEX-UHFFFAOYSA-N 0.000 description 1
- BTSRWVQHIOZQAE-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-phenylprop-2-yn-1-one Chemical compound C1=CC(Cl)=CC=C1C#CC(=O)C1=CC=CC=C1 BTSRWVQHIOZQAE-UHFFFAOYSA-N 0.000 description 1
- MQSKETRVYKOPJF-UHFFFAOYSA-N 3-(4-methylphenyl)-1-phenylprop-2-yn-1-ol Chemical compound C1=CC(C)=CC=C1C#CC(O)C1=CC=CC=C1 MQSKETRVYKOPJF-UHFFFAOYSA-N 0.000 description 1
- ODMJODNPAIICIH-UHFFFAOYSA-N 3-(4-methylphenyl)-1-phenylprop-2-yn-1-one Chemical compound C1=CC(C)=CC=C1C#CC(=O)C1=CC=CC=C1 ODMJODNPAIICIH-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- DORMTBIPKNPJPY-UHFFFAOYSA-N acetic acid;iodobenzene Chemical compound CC(O)=O.IC1=CC=CC=C1 DORMTBIPKNPJPY-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a preparation method of propargyl alcohol compounds, which is characterized in that propargyl alcohol compounds react in acetonitrile at room temperature under the oxidation of N-iodosuccinimide (NIS) to obtain various propargyl acetone compounds. The method has the advantages of simple and convenient reaction operation, high reaction rate, good product specificity, few byproducts, high yield, cheap and easily obtained oxidant and good tolerance to functional groups. The invention provides a mild new method for oxidizing propargyl alcohol into propargyl acetone for the first time.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of an propargyl acetone compound.
Background
The synthesis of carbonyl compounds by oxidation of alcohols is one of the most basic and widely used processes in organic synthesis. Because the propargyl alcohol compound has the advantages of low price, easy obtaining and the like, and the propargyl acetone compound not only has a plurality of active reaction sites, but also is an important precursor for constructing a complex compound, the oxidation of the propargyl alcohol compound to generate the propargyl acetone compound has important significance. In literature reports, such reactions typically require catalytic oxidation using metal catalysts (chromium, manganese, ruthenium, osmium, etc.), high-valent iodine reagents (iodobenzene acetate, etc.), TEMPO, etc. However, the above method has the disadvantages of severe reaction conditions, more by-products, poor selectivity, and expensive catalyst or oxidant, so it is very valuable to develop a convenient, efficient, safe and mild oxidation method. The invention provides a mild new method for oxidizing propargyl alcohol into propargyl acetone.
Disclosure of Invention
The object of the present invention is to provide a mild, novel process for the selective oxidation of propargyl alcohol to propargyl acetone. The method has the characteristics of high reaction rate, high product specificity, few byproducts, high yield and cheap and easily-obtained oxidant, and can oxidize a plurality of propargylic alcohol compounds to generate propargylic acetone compounds.
The technical scheme of the method is as follows:
a method for synthesizing an alkynylacetone compound is characterized by comprising the following steps: propargyl alcohol (formula I) is reacted in acetonitrile at room temperature under oxidation of N-iodosuccinimide (NIS) to give various propargyl acetone compounds (formula II) of the following formula:
in the above reaction formula: r1Is hydrogen, methyl, ethyl or halogen; r of the propargyl alcohol1The groups may be in any position of the phenyl ring. R2Is hydrogen, methyl, ethyl or halogen; r of the propargyl alcohol2The groups may be in any position of the phenyl ring.
The method of the invention has good adaptability to functional groups, R of propargyl alcohol1,R2The substituent may be a methyl group, an ethyl group or a halogen atom in addition to a hydrogen atom, and the position of the substituent is not particularly limited, and may be the 2-position, the 3-position or the 4-position.
The above halogen means a fluorine, chlorine, bromine or iodine atom, preferably chlorine and bromine.
The propargyl alcohol used in the process of the invention is a synthesis reagent and can be synthesized conventionally according to the literature.
The oxidant used in the method is N-iodosuccinimide [ NIS ], which is a commercialized reagent and does not need special treatment; the amount is preferably in the range of 1.2 equivalents based on the propargyl alcohol.
The amount of acetonitrile used in the process of the invention is calculated as 5 ml of acetonitrile per mmol of propargyl alcohol.
The temperature of the above reaction was 25 deg.CoC。
The reaction time varies depending onThe raw materials of (A) are slightly different, and thin-layer chromatography can be adopted for monitoring based on the fact that propargyl alcohol is completely reacted. In an air atmosphere, 25oAnd C, reacting for 4-5 hours.
The method of the invention realizes the preparation of the propargyl acetone compound from the propargyl alcohol under mild conditions for the first time. The method has the advantages of high reaction efficiency, good economy, high synthesis rate and the like, and can be widely applied to preparation of various propargyl acetone compounds. Specifically, the present invention has the following advantages:
1. the propargyl acetone prepared by the method has potential application value in the fields of organic synthesis, drug research and development and the like, and the used oxidant is convenient and easy to obtain;
2. the invention has the characteristics of simple and convenient operation, good specificity and high yield;
3. the reaction conditions involved in the method of the invention are mild, 25oAnd reacting for 4-5 hours under C to prepare various substituted propargyl acetone compounds.
Detailed Description
The invention is further described below with reference to examples, but the scope of practice of the invention is not limited in any way.
Example 1
Synthesis of 1, 3-diphenyl-2-alkyne-1-one
41.6 mg (i.e., 0.2 mmol) of 1, 3-diphenyl-2-yn-1-ol and 54mg (i.e., 0.24 mmol) were sequentially added to a 10 mL glass reaction tubeNIodo-succinimide, followed by 1 mL acetonitrile, under air atmosphere at 25 deg.CoC was stirred for 4 hours, reacted and concentrated to yield a mixture of petroleum ether: ethyl acetate is used as eluent with the volume ratio of 150:1, and the 1, 3-diphenyl-2-alkyne-1-ketone can be obtained by silica gel column chromatography purification, and the structure of the compound is shown as the following formula:
the compound was an orange yellow solid with a yield of 91% and the nuclear magnetic data were as follows:
1H NMR (500 MHz, CDCl3) δ 8.27 (s, 1H), 8.25 (d, J = 1.2 Hz, 1H), 7.73 (s, 1H), 7.71 (d,J = 1.3 Hz, 1H), 7.66 (t, J = 7.4 Hz, 1H), 7.55 (t, J = 7.7 Hz, 2H), 7.51 (d,J = 7.4 Hz, 1H), 7.46 (t, J = 7.4 Hz, 2H).
example 2
Synthesis of 1-phenyl-3- (p-tolyl) prop-2-yn-1-one
To a 10 mL glass reaction tube were added 44.4mg (i.e., 0.2 mmol) of 1-phenyl-3- (p-tolyl) prop-2-yn-1-ol, 54mg (i.e., 0.24 mmol) in this orderNIodo-succinimide, followed by 1 mL acetonitrile, under air atmosphere at 25 deg.CoC was stirred for 4 hours, reacted and concentrated to yield a mixture of petroleum ether: ethyl acetate is used as eluent with the volume ratio of 150:1, and the 1-phenyl-3- (p-tolyl) prop-2-alkyne-1-ketone can be obtained by silica gel column chromatography purification, and the structure of the compound is shown as the following formula:
the compound was an orange yellow solid with a yield of 82% and the nuclear magnetic data were as follows:
1H NMR (500 MHz, CDCl3) δ 8.24 (s, 1H), 8.23 – 8.22 (m, 1H), 7.63 (ddd, J= 9.6, 2.4, 1.2 Hz, 1H), 7.59 (d,J = 7.7 Hz, 2H), 7.52 (t, J = 7.6 Hz, 2H), 7.24 (d,J = 7.9 Hz, 2H), 2.41 (s, 3H).
example 3
Synthesis of 3- (4-chlorophenyl) -1-phenylpropan-2-yn-1-one
To a 10 mL glass reaction tube were added 48.4mg (i.e., 0.2 mmol) of 3- (4-chlorophenyl) -1-phenylpropan-2-yn-1-ol, 54mg (i.e., 0.24 mmol) in that orderNIodo-succinimide, followed by 1 mL acetonitrile, under air atmosphere at 25 deg.CoC was stirred for 5 hours, reacted and concentrated to yield a mixture of petroleum ether: ethyl acetate is used as eluent with the volume ratio of 150:1, and the 3- (4-chlorphenyl) -1-phenylpropane-2-alkyne-1-ketone can be obtained by silica gel column chromatography purification, and the structure of the compound is shown as the following formula:
the compound was a pale yellow solid with a yield of 85% and the nuclear magnetic data were as follows:
1H NMR (500 MHz, CDCl3) δ 8.22 (s, 1H), 8.20 (d, J = 1.3 Hz, 1H), 7.67 – 7.62 (m, 2H), 7.62 (d,J = 1.9 Hz, 1H), 7.53 (t, J = 7.7 Hz, 2H), 7.42 (d, J= 1.8 Hz, 1H), 7.41 (d,J = 1.7 Hz, 1H).
example 4
Synthesis of 1- (4-bromophenyl) -3-phenylpropan-2-yn-1-one
To a 10 mL glass reaction tube were added 57.2mg (i.e., 0.2 mmol) of 1- (4-bromophenyl) -3-phenylprop-2-yn-1-ol, 54mg (i.e., 0.24 mmol) in that orderNIodo-succinimide, followed by 1 mL acetonitrile, under air atmosphere at 25 deg.CoC was stirred for 5 hours, reacted and concentrated to yield a mixture of petroleum ether: the volume ratio of ethyl acetate is 150:1, and the 1- (4-bromophenyl) -3-phenylpropan-2-alkyne-1-ketone can be obtained by silica gel column chromatography purification, and the structure of the eluent is shown as the following formula:
the compound was a pale yellow solid with a yield of 75% and the nuclear magnetic data were as follows:
1H NMR (500 MHz, CDCl3) δ 8.09 – 8.08 (m, 1H), 8.08 – 8.07 (m, 1H), 7.69 (s, 1H), 7.68 (q,J = 1.9 Hz, 2H), 7.66 (d, J = 1.8 Hz, 1H), 7.52 – 7.48 (m, 1H), 7.45 – 7.42 (m, 2H).
example 5
Synthesis of 1- (naphthalen-2-yl) -3-phenylpropan-2-yn-1-ol
To a 10 mL glass reaction tube were added 57.6mg (i.e., 0.2 mmol) of 1- (naphthalen-2-yl) -3-phenylprop-2-yn-1-ol, 54mg (i.e., 0.24 mmol)NIodo-succinimide, followed by 1 mL acetonitrile, under air atmosphere at 25 deg.CoC was stirred for 5 hours, reacted and concentrated to yield a mixture of petroleum ether: ethyl acetate volume ratio of 150:1 as eluent, purifying by silica gel column chromatography to obtain 1- (naphthalene-2-yl) -3-phenylpropan-2-alkyne-1-ketones having the structure represented by the following formula:
the compound was a pale yellow solid with 73% yield and the following nuclear magnetic data:
1H NMR (500 MHz, CDC3) δ 8.27 (d, J = 2.0 Hz, 1H), 8.05 – 8.02 (m, 1H), 7.71 – 7.67 (m, 2H), 7.62 – 7.59 (m, 1H), 7.52 (ddd,J = 7.3, 3.7, 1.3 Hz, 1H), 7.47 – 7.42 (m, 2H).。
Claims (4)
1. a method for preparing an alkynylacetone compound, which comprises the following stepsN-oxidation of iodosuccinimide, reaction of propargyl alcohol of formula I in acetonitrile to give an propargyl acetonide of formula II:
wherein R is1 ，R2Is a hydrogen atom, a methyl group, an ethyl group or a halogen atom.
2. The process of claim 1, wherein the molar ratio of reactants fed is propargyl alcohol:Niodo-succinimide = 1: 1.2.
3. The process of claim 1, wherein the amount of acetonitrile used is 5 ml per mmol of propargyl alcohol.
4. The method of claim 1, wherein the reaction is carried out in an air atmosphere at a temperature of 25 deg.foAnd C, the reaction time is 4-5 hours.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880617A (en) * | 2012-12-20 | 2014-06-25 | 中国科学院大连化学物理研究所 | Method for preparing acetylenic ketone through oxidizing propargyl alcohol |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880617A (en) * | 2012-12-20 | 2014-06-25 | 中国科学院大连化学物理研究所 | Method for preparing acetylenic ketone through oxidizing propargyl alcohol |
Non-Patent Citations (2)
| Title |
|---|
| KARL O. HESSIAN AND BERNARD L. FLYNN: "Selective endo and exo Iodocyclizations in the Synthesis of Quinolines and Indoles", 《ORGANIC LETTERS》 * |
| LIN，CF等: "Synthesis of 3-halogenated flavonoids via electrophile-prornoted cyclization of 2-(3-aryl-2-propynoyl)anisoles", 《JOURNAL OF THE CHINESE CHEMICAL SOCIETY》 * |
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