CN112939753B - Synthesis method of 1-indanone compound - Google Patents

Synthesis method of 1-indanone compound Download PDF

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CN112939753B
CN112939753B CN202010968342.8A CN202010968342A CN112939753B CN 112939753 B CN112939753 B CN 112939753B CN 202010968342 A CN202010968342 A CN 202010968342A CN 112939753 B CN112939753 B CN 112939753B
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张玉红
于书玲
刘占祥
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Zhejiang University ZJU
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    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
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Abstract

The invention provides a synthesis method of a 1-indanone compound, which comprises the following steps: adding a benzoic acid compound, dimethyl malonate, paraformaldehyde, a rhodium catalyst and alkali into an organic solvent, heating under the condition of nitrogen for reaction, and after the reaction is completed, carrying out post-treatment to obtain the 1-indanone compound. The invention provides a method for synthesizing 1-indanone compounds, which has the advantages of simple and convenient operation, cheap and easily obtained substrate, wide universality and good functional group compatibility, and provides a simple and efficient method for synthesizing indanone derivatives with diversified structures.

Description

Synthesis method of 1-indanone compound
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a synthesis method of a 1-indanone compound.
Background
The 1-indanone compounds are very important and universal frameworks, widely exist in bioactive molecules and drug molecules, are important substrates for screening the activity of drug molecules, and are also important intermediates for pharmaceutical chemistry and organic synthesis. Chemists have developed many methods to build this important backbone, such as Friedel-Crafts acylation of aromatics, Nazarov cyclization. These methods generally require pre-functionalization of the substrate, lengthy reaction steps, and harsh reaction conditions. Therefore, it is necessary to develop a novel and efficient method for constructing the 1-indanone skeleton compounds.
The transition metal catalyzed C-H bond activation strategy assisted by a guide group provides an atom economical and step economical method for efficiently synthesizing complex molecules through decades of development. In recent years, methods for synthesizing 1-indanones by activating C-H bonds have been reported. Different directing groups have been used in these processes for the construction of indanones, such as amides and thioylide-type directing groups. However, these directing groups often require pre-installation, adding synthetic steps and limiting the synthetic applications of the method. Carboxyl groups are common functional groups widely present in organic molecules, while carboxylic acids are readily available starting materials in organic synthesis. Based on the availability of carboxylic acids that are inexpensive and can act as traceless directing groups, much attention has been focused on carboxylic acid-directed C-H activation reactions. Despite the tremendous advances made in this area, applications for the construction of complex molecules for carboxylic acid-directed multicomponent reactions have not been fully developed.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a method for synthesizing 1-indanone compounds, which has the advantages of simple and convenient operation, cheap and easily-obtained substrate, wide universality and good functional group compatibility, and provides a simple and efficient method for synthesizing indanone derivatives with diversified structures.
A method for synthesizing 1-indanone compounds comprises the following steps: adding a benzoic acid compound, dimethyl malonate, paraformaldehyde, a rhodium catalyst and alkali into an organic solvent, heating under the condition of nitrogen for reaction, and after the reaction is completed, carrying out post-treatment to obtain the 1-indanone compound;
the specific reaction process is as follows:
Figure BDA0002683155050000021
wherein, R is one of benzyl, alkyl, methoxy and halogen, preferably one or more of benzyl, methyl, methoxy, F, Cl or Br.
Preferably, the chemical formula of the 1-indanone compound is one of the compounds shown in formula (I-1) to formula (I-12):
Figure BDA0002683155050000022
Figure BDA0002683155050000031
preferably, the organic solvent is Hexafluoroisopropanol (HFIP).
Preferably, the base is sodium acetate.
Preferably, the rhodium catalyst is pentamethylcyclopentadienylrhodium dichloride.
The reaction temperature under the nitrogen condition is preferably 150-160 ℃, and more preferably 150 ℃. The reaction time is preferably 12 to 18 hours, and more preferably 18 hours. .
Preferably, the molar ratio of the rhodium catalyst to the benzoic acid compound is (0.03-0.07): 1, more preferably 0.05: 1.
preferably, the molar ratio of the base to the benzoic acid compound is (0.8 to 1.2): 1, more preferably 1: 1.
preferably, the molar ratio of the benzoic acid compound, the dimethyl malonate, and the paraformaldehyde is 1: (1.5-2.5): (1.5-2.5), more preferably 1: 2: 2.
preferably, the post-treatment comprises cooling, suction filtration, silica gel sample mixing and column chromatography purification.
Compared with the prior art, the invention has the beneficial effects that:
(1) the 1-indanone compound is synthesized by a simple and easily-obtained raw material multi-component one-pot method, so that the conversion efficiency is high, and the economical efficiency of the steps is good;
(2) the synthetic method disclosed by the invention is simple to operate, high in reaction yield, and very good in substrate universality and functional group compatibility.
Drawings
FIG. 1 is a hydrogen spectrum and a carbon spectrum of a compound obtained in example 1 of the present invention;
FIG. 2 is a graph showing a hydrogen spectrum and a carbon spectrum of a compound obtained in example 2 of the present invention;
FIG. 3 shows a hydrogen spectrum and a carbon spectrum of a compound obtained in example 3 of the present invention;
FIG. 4 is a graph showing a hydrogen spectrum and a carbon spectrum of a compound obtained in example 4 of the present invention;
FIG. 5 shows a hydrogen spectrum and a carbon spectrum of a compound obtained in example 5 of the present invention;
FIG. 6 shows a hydrogen spectrum and a carbon spectrum of a compound obtained in example 6 of the present invention;
FIG. 7 shows a hydrogen spectrum and a carbon spectrum of a compound obtained in example 7 of the present invention;
FIG. 8 is a graph showing a hydrogen spectrum and a carbon spectrum of a compound obtained in example 8 of the present invention;
FIG. 9 shows a hydrogen spectrum and a carbon spectrum of a compound obtained in example 9 of the present invention;
FIG. 10 shows a hydrogen spectrum and a carbon spectrum of a compound obtained in example 10 of the present invention;
FIG. 11 is a graph showing a hydrogen spectrum and a carbon spectrum of a compound obtained in example 11 of the present invention;
FIG. 12 shows a hydrogen spectrum and a carbon spectrum of a compound obtained in example 12 of the present invention.
Detailed Description
The present invention will be further described with reference to specific examples, which are intended to be preferred embodiments of the invention.
Examples 1 to 12
Adding benzoic acid compound (0.3mmol), dimethyl malonate (0.6mmol), paraformaldehyde (0.6mmol), pentamethylcyclopentadienyl rhodium dichloride (0.015mmol), sodium acetate (0.3mmol) and 0.4ml of organic solvent into a test tube according to the raw material ratio shown in the table 1, uniformly mixing and stirring, respectively reacting according to the reaction conditions shown in the table 2 in the presence of nitrogen, cooling, performing suction filtration, mixing a sample with silica gel, and performing column chromatography purification to obtain corresponding 1-indanone compound (I);
the data of the 1-indanone compound (I) are represented in the figures 1-12, wherein a hydrogen spectrum is tested on a 400MHz nuclear magnetic instrument, and a carbon spectrum is tested on a 100MHz nuclear magnetic instrument; testing conditions are that tetramethylsilane is used as an internal standard at room temperature, and a sample is dissolved by deuterated chloroform;
the above reaction process is shown as the following formula:
Figure BDA0002683155050000051
TABLE 1 raw material ratios of examples 1 to 12
Figure BDA0002683155050000052
TABLE 2 reaction conditions and reaction results of examples 1 to 12
Figure BDA0002683155050000053
Figure BDA0002683155050000061
In tables 1 and 2, T is the reaction temperature, T is the reaction time, Bn is benzyl, 1-naphthyl is 1-substituted naphthyl, and 1-tetrahydronaphtyl is 1-substituted tetrahydronaphthyl.
The structures and related data of the partial compounds prepared in examples 1-12 are as follows:
Figure BDA0002683155050000062
7-methyl-2, 3-dihydro-1H-inden-1-one (I-1): purification by column chromatography (petroleum ether: EtOAc ═ 15: 1) gave a white solid (35.5mg, 81%) with a melting point of 48-49 ℃.
1H NMR(400MHz,CDCl3)δ7.42(t,J＝7.6Hz,1H),7.27(d,J＝7.6Hz,1H),7.09(d,J＝7.6Hz,1H),3.08(t,J＝6.0Hz,2H),2.67-2.65(m,2H),2.63(s,3H)；13C NMR(100MHz,CDCl3)δ208.1,156.0,138.9,134.5,134.0,129.1,124.0,36.8,25.4,18.4.
Figure BDA0002683155050000063
7-benzyl-2, 3-dihydro-1H-inden-1-one (I-2): purification by column chromatography (petroleum ether: EtOAc ═ 15: 1) gave a white solid (46.7mg, 70%) with a melting point of 77-79 ℃.
1H NMR(400MHz,CDCl3)δ7.43(t,J＝7.6Hz,1H),7.29(d,J＝7.6Hz,1H),7.26-7.25(m,4H),7.20-7.15(m,1H),7.05(d,J＝7.6Hz,1H),4.48(s,2H),3.08(t,J＝6.4Hz,2H),2.68-2.66(m,2H)；13C NMR(100MHz,CDCl3)δ207.7,156.2,141.8,140.5,134.2,133.9,129.3,128.7,128.4,126.0,124.6,36.9,36.6,25.3.HRMS(EI-TOF)calcd for C16H14O(M+):222.1045,found:222.1043.
Figure BDA0002683155050000071
7-methoxy-2, 3-dihydro-1H-inden-1-one (I-3): purification by column chromatography (petroleum ether: EtOAc ═ 3: 1) gave a pale yellow solid (41.8mg, 86%), mp 92-93 ℃.
1H NMR(400MHz,CDCl3)δ7.49(t,J＝8.0Hz,1H),6.98(d,J＝7.6Hz,1H),6.75(d,J＝8.0Hz,1H),3.92(s,3H),3.05(t,J＝6.4Hz,2H),2.65-2.62(m,2H)；13C NMR(100MHz,CDCl3)δ204.9,158.1,158.0,136.4,125.2,118.4,108.8,55.7,36.8,25.6.
Figure BDA0002683155050000072
6-bromo-7-methyl-2, 3-dihydro-1H-indan-1-one (I-4): purification by column chromatography (petroleum ether: EtOAc ═ 20: 1) gave a yellow solid (27.0mg, 40%) m.p. 82-83 ℃.
1H NMR(400MHz,CDCl3)δ7.68(d,J＝8.4Hz,1H),7.15(d,J＝8.0Hz,1H),3.01(t,J＝6.4Hz,2H),2.71(s,3H),2.70-2.68(m,2H)；13C NMR(100MHz,CDCl3)δ206.8,155.1,138.6,137.6,135.8,125.3,125.0,37.1,24.7,17.0.HRMS(EI-TOF)calcd for C10H9BrO(M+):223.9837,found:223.9838.
Figure BDA0002683155050000081
6, 7-dimethoxy-2, 3-dihydro-1H-inden-1-one (I-5): purification by column chromatography (petroleum ether: EtOAc ═ 3: 1) gave a white solid (38.1mg, 66%) with a melting point of 41-42 ℃.
1H NMR(400MHz,CDCl3)δ7.17(d,J＝8.4Hz,1H),7.09(d,J＝8.0Hz,1H),3.99(s,3H),3.87(s,3H),3.02(t,J＝6.4Hz,2H),2.70-2.67(m,2H)；13C NMR(100MHz,CDCl3)δ204.6,151.2,148.1,147.2,129.6,121.2,120.3,61.9,57.0,37.7,24.8.
Figure BDA0002683155050000082
5, 7-dimethyl-2, 3-dihydro-1H-inden-1-one (I-6): purification by column chromatography (petroleum ether: EtOAc ═ 15: 1) gave a white solid (36.0mg, 75%) with a melting point of 75-76 ℃.
1H NMR(400MHz,CDCl3)δ7.07(s,1H),6.91(s,1H),3.02(t,J＝6.4Hz,2H),2.65-2.62(m,2H),2.59(s,3H),2.38(s,3H)；13C NMR(100MHz,CDCl3)δ207.5,156.5,145.0,138.6,132.3,130.3,124.4,37.0,25.2,21.8,18.2.
Figure BDA0002683155050000091
5-fluoro-7-methyl-2, 3-dihydro-1H-inden-1-one (I-7): purification by column chromatography (petroleum ether: EtOAc ═ 15: 1) gave a pale yellow solid (35.5mg, 72%) with a melting point of 49-50 ℃.
1H NMR(400MHz,CDCl3)δ6.92(d,J＝8.4Hz,1H),6.80(d,J＝9.6Hz,1H),3.06(t,J＝6.4Hz,2H),2.69-2.66(m,2H),2.62(s,3H)；13C NMR(100MHz,CDCl3)δ206.1,166.31(d,JC-F＝253.0Hz),158.9(d,JC-F＝11.0Hz),141.9(d,JC-F＝11.0Hz),131.0,116.8(d,JC-F＝23.0Hz),110.5(d,JC-F＝22.0Hz),37.1,25.5(d,JC-F＝3.0Hz),18.4.HRMS(EI-TOF)calcd for C10H9FO(M+):164.0637,found:164.0638.
Figure BDA0002683155050000092
5-chloro-7-methyl-2, 3-dihydro-1H-inden-1-one (I-8): purification by column chromatography (petroleum ether: EtOAc ═ 20: 1) gave a yellow solid (25.5mg, 47%) melting point 59-60 ℃.
1H NMR(400MHz,CDCl3)δ7.19(s,1H),7.02(s,1H),2.99(t,J＝6.4Hz,2H),2.62-2.59(m,2H),2.53(s,3H)；13C NMR(100MHz,CDCl3)δ206.5,157.4,140.4,140.2,133.0,129.5,124.1,36.9,25.2,18.1.HRMS(EI-TOF)calcd for C10H9ClO(M+):180.0342,found:180.0342.
Figure BDA0002683155050000101
5-chloro-7-methoxy-2, 3-dihydro-1H-inden-1-one (I-9): purification by column chromatography (petroleum ether: EtOAc ═ 3: 1) gave a white solid (45.4mg, 77%), mp 114-.
1H NMR(400MHz,CDCl3)δ6.98(s,1H),6.74(s,1H),3.91(s,3H),3.03(t,J＝6.4Hz,2H),2.66-2.63(m,2H)；13C NMR(100MHz,CDCl3)δ203.4,159.0,158.2,142.4,123.9,118.7,110.1,56.1,36.8,25.6.HRMS(EI-TOF)calcd for C10H9ClO2(M+):196.0291,found:196.0290.
Figure BDA0002683155050000102
5-bromo-7-methoxy-2, 3-dihydro-1H-inden-1-one (I-10): purification by column chromatography (petroleum ether: EtOAc ═ 3: 1) gave a white solid (44.8mg, 62%), mp 105-.
1H NMR(400MHz,CDCl3)δ7.17(s,1H),6.91(s,1H),3.92(s,3H),3.04(t,J＝6.4Hz,2H),2.66-2.63(m,2H)；13C NMR(100MHz,CDCl3)δ203.6,159.1,158.1,131.0,124.3,121.8,113.0,56.2,36.7,25.5.HRMS(EI-TOF)calcd for C10H9BrO2(M+):239.9786,found:239.9784.
Figure BDA0002683155050000103
2,3,6,7,8, 9-hexahydro-1H-cyclopenta [ a ] naphthalen-1-one (I-11): purification by column chromatography (petroleum ether: EtOAc ═ 15: 1) gave a yellow oil (33.5mg, 60%).
1H NMR(400MHz,CDCl3)δ7.24(d,J＝8.0Hz,1H),7.16(d,J＝8.0Hz,1H),3.19-3.18(m,2H),3.02(t,J＝6.0Hz,2H),2.79-2.78(m,2H),2.65-2.62(m,2H),1.80-1.77(m,4H)；13C NMR(100MHz,CDCl3)δ208.2,154.1,137.9,136.3,135.6,134.1,123.4,37.1,29.4,25.8,25.1,22.7,22.5.
Figure BDA0002683155050000111
2, 3-dihydro-1H-cyclopenta [ a ] naphthalen-1-one (I-12): purification by column chromatography (petroleum ether: EtOAc: 15: 1) gave a white solid (36.6mg, 67%), m.p. 101-.
1H NMR(400MHz,CDCl3)δ9.15(d,J＝8.4Hz,1H),8.01(d,J＝8.4Hz,1H),7.87(d,J＝8.4Hz,1H),7.68-7.64(m,1H),7.56-7.52(m,1H),7.48(d,J＝8.4Hz,1H),3.18(t,J＝5.6Hz,2H),2.79-2.76(m,2H)；13C NMR(100MHz,CDCl3)δ207.6,158.5,135.7,132.6,131.1,129.4,128.9,128.1,126.6,124.1,124.0,36.9,26.2。

Claims (9)

1. A method for synthesizing 1-indanone compounds is characterized by comprising the following steps: adding a benzoic acid compound, dimethyl malonate, paraformaldehyde, a rhodium catalyst and alkali into an organic solvent, heating under the condition of nitrogen for reaction, and after the reaction is completed, carrying out post-treatment to obtain the 1-indanone compound;
the structure of the benzoic acid compound is shown as the formula (II):
Figure DEST_PATH_IMAGE002
（II）；
the structure of the dimethyl malonate is shown as the formula (III):
Figure DEST_PATH_IMAGE004
（III）；
the structure of the 1-indanone compound is shown as the formula (I):
Figure DEST_PATH_IMAGE006
（I）；
in the formulas (I) - (II), R is one or more of benzyl, alkyl, methoxy and halogen;
the rhodium catalyst is pentamethylcyclopentadienyl rhodium dichloride.
2. The method for synthesizing the 1-indanone compound according to claim 1, wherein R is one or more of benzyl, methyl, methoxy, F, Cl or Br.
3. The method for synthesizing the 1-indanone compound according to claim 1, wherein the chemical formula of the 1-indanone compound is one of compounds represented by formula (I-1) to formula (I-10):
Figure DEST_PATH_IMAGE008
（I-1）；
Figure DEST_PATH_IMAGE010
（I-2）；
Figure DEST_PATH_IMAGE012
（I-3）；
Figure DEST_PATH_IMAGE014
（I-4）；
Figure DEST_PATH_IMAGE016
（I-5）；
Figure DEST_PATH_IMAGE018
（I-6）；
Figure DEST_PATH_IMAGE020
（I-7）；
Figure DEST_PATH_IMAGE022
（I-8）；
Figure DEST_PATH_IMAGE024
（I-9）；
Figure DEST_PATH_IMAGE026
（I-10）。
4. the method for synthesizing 1-indanone compounds according to claim 1, wherein the organic solvent is hexafluoroisopropanol.
5. The method for synthesizing 1-indanone compounds according to claim 1, wherein the alkali is sodium acetate.
6. The method for synthesizing the 1-indanone compound according to claim 1, wherein the reaction temperature is 150-160 ℃ and the reaction time is 12-18 hours under the nitrogen condition.
7. The method for synthesizing 1-indanone compounds according to claim 1, wherein the molar ratio of the rhodium catalyst to the benzoic acid compounds is (0.03-0.07): 1.
8. the method for synthesizing 1-indanone compounds according to claim 1, wherein the molar ratio of the base to the benzoic acid compound is (0.8-1.2): 1.
9. the method for synthesizing 1-indanone compounds according to claim 1, wherein the molar ratio of the benzoic acid compound, the dimethyl malonate, and the paraformaldehyde is 1: (1.5-2.5): (1.5-2.5).
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JP2013227271A (en) * 2012-03-29 2013-11-07 Japan Polyethylene Corp Metallocene compound, olefin polymerization catalyst component and olefin polymerization catalyst including the same, and method of producing olefine polymer using the olefin polymerization catalyst

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CN101318887A (en) * 2008-07-08 2008-12-10 上海化工研究院 Method for preparing indene compounds
JP2013227271A (en) * 2012-03-29 2013-11-07 Japan Polyethylene Corp Metallocene compound, olefin polymerization catalyst component and olefin polymerization catalyst including the same, and method of producing olefine polymer using the olefin polymerization catalyst

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