CN106810592A - A kind of synthesis technique of the diketone steroidal of 4 alkene 3,6 - Google Patents
A kind of synthesis technique of the diketone steroidal of 4 alkene 3,6 Download PDFInfo
- Publication number
- CN106810592A CN106810592A CN201611073481.4A CN201611073481A CN106810592A CN 106810592 A CN106810592 A CN 106810592A CN 201611073481 A CN201611073481 A CN 201611073481A CN 106810592 A CN106810592 A CN 106810592A
- Authority
- CN
- China
- Prior art keywords
- alkene
- acetone
- diketone
- jones
- oxidants
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The present invention relates to a kind of synthesis technique of the diketone steroidal of 4 alkene 3,6, the technique is comprised the following steps：1mol Chinese yam saponins are dissolved in the acetone of 1000g 25000g, 1500g 8000g Jones oxidants are added under conditions of 10 DEG C to 50 DEG C, stirring reaction 1 hour, it is subsequently adding isopropanol and removes excessive oxidant, concentration removes acetone, add water precipitation product, by obtaining finished product after centrifugation, refined, drying.Beneficial effects of the present invention are：The present invention uses the Jones oxidants of appropriate equivalent, and a step completes this change under certain condition, greatly simplifies technological process and improves yield, and product purity is high.
Description
Technical field
The invention belongs to organic synthesis technology field, more particularly to a kind of 4- alkene -3, the synthesis technique of 6- diketone steroidals.
Background technology
By synthesis technique A, B rings are transformed into 4- alkene -3 for the steroidal of the alkene structure of 3- hydroxyls -5, and 6- diketone steroidals are commonly used
Route be 5- alkene epoxidations, then open loop becomes 5,6- glycol, then 3,6- dihydroxy is oxidized to diketone with oxidant, finally
Eliminate 5- hydroxyls and obtain 4- alkene, this process is divided into four-step reaction completion, and cumbersome, yield is not high.
The content of the invention
It is an object of the invention to overcome the shortcomings of that prior art is present, and a kind of 4- alkene -3 are provided, 6- diketone steroidals
Synthesis technique, is a kind of steroidal A, B ring structure reforming technologies.
The purpose of the present invention is completed by following technical solution, this 4- alkene -3, the synthesis work of 6- diketone steroidals
Skill, the technique is comprised the following steps：1mol Chinese yam saponins are dissolved in the acetone of 1000g-25000g, at -10 DEG C to 50 DEG C
Under conditions of add 1500g-8000g Jones oxidants, stirring reaction 1 hour is subsequently adding isopropanol and removes excessive oxygen
Agent, concentration removes acetone, and add water precipitation product, by obtaining finished product after centrifugation, refined, drying.
Beneficial effects of the present invention are：The present invention uses the Jones oxidants of appropriate equivalent, and a step is complete under certain condition
Into this change, greatly simplifie technological process and improve yield, product purity is high.
Specific embodiment
Detailed introduction will be done to the present invention below：
This 4- alkene -3 of the present invention, the synthesis technique of 6- diketone steroidals, technique is comprised the following steps：By 1mol
Chinese yam saponin is dissolved in the acetone of 1000g-25000g, and 1500g-8000g Jones are added under conditions of -10 DEG C to 50 DEG C
Oxidant, stirring reaction 1 hour is subsequently adding isopropanol and removes excessive oxidant, and concentration removes acetone, and the precipitation that adds water is produced
Thing, by obtaining finished product after centrifugation, refined, drying.
The present invention relates to a kind of steroidal A, B ring structure reforming technologies can easily the alkene of 3- hydroxyls -5 by the technique
Steroidal is oxidized to 4- alkene -3,6- diketone steroidals, and representative instance includes but is not limited to Chinese yam saponin to be oxidized to 25R- spiral shell steroids -4-
Alkene -3,6- diketone.To synthesize 25R- spiral shell Gona-4-ene-3s, as a example by 6- diketone.
Embodiment 1：1mol Chinese yam saponins are dissolved in the acetone of 1000g, 1500g is added under conditions of -10 DEG C
Jones oxidants, stirring reaction 1 hour is subsequently adding isopropanol and removes excessive oxidant, and concentration removes acetone, and add water analysis
Go out product, by obtaining finished product after centrifugation, refined, drying.
Embodiment 2：1mol Chinese yam saponins are dissolved in the acetone of 25000g, 8000g is added under conditions of 50 DEG C
Jones oxidants.Stirring reaction 1 hour, is subsequently adding isopropanol and removes excessive oxidant, and concentration removes acetone, and add water analysis
Go out product, by obtaining finished product after centrifugation, refined, drying.
Embodiment 3：1mol Chinese yam saponins are dissolved in the acetone of 8000g, 5000g is added under conditions of 10 DEG C
Jones oxidants.Stirring reaction 1 hour, is subsequently adding isopropanol and removes excessive oxidant, and concentration removes acetone, and add water analysis
Go out product, by obtaining finished product after centrifugation, refined, drying.
It is understood that it will be understood by those skilled in the art that being subject to technical scheme and inventive concept
The protection domain of appended claims of the invention should all be belonged to replacement or change.
Claims (4)
1. a kind of 4- alkene -3, the synthesis technique of 6- diketone steroidals, it is characterised in that：The technique is comprised the following steps：By 1mol potatos
Saponin is dissolved in the acetone of 1000g-25000g Chinese yam, and 1500g-8000g Jones oxygen is added under conditions of -10 DEG C to 50 DEG C
Agent, stirring reaction 1 hour is subsequently adding isopropanol and removes excessive oxidant, and concentration removes acetone, and add water precipitation product,
By obtaining finished product after centrifugation, refined, drying.
2. 4- alkene -3 according to claim 1, the synthesis technique of 6- diketone steroidals, it is characterised in that：By 1mol Chinese yam soaps
Element is dissolved in the acetone of 1000g, and 1500g Jones oxidants are added under conditions of -10 DEG C.
3. 4- alkene -3 according to claim 1, the synthesis technique of 6- diketone steroidals, it is characterised in that：By 1mol Chinese yam soaps
Element is dissolved in the acetone of 25000g, and 8000g Jones oxidants are added under conditions of 50 DEG C.
4. 4- alkene -3 according to claim 1, the synthesis technique of 6- diketone steroidals, it is characterised in that：By 1mol Chinese yam soaps
Element is dissolved in the acetone of 8000g, and 5000g Jones oxidants are added under conditions of 10 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611073481.4A CN106810592A (en) | 2016-11-29 | 2016-11-29 | A kind of synthesis technique of the diketone steroidal of 4 alkene 3,6 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611073481.4A CN106810592A (en) | 2016-11-29 | 2016-11-29 | A kind of synthesis technique of the diketone steroidal of 4 alkene 3,6 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106810592A true CN106810592A (en) | 2017-06-09 |
Family
ID=59107004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201611073481.4A Pending CN106810592A (en) | 2016-11-29 | 2016-11-29 | A kind of synthesis technique of the diketone steroidal of 4 alkene 3,6 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106810592A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004037845A1 (en) * | 2002-10-28 | 2004-05-06 | Phytopharm Plc | Stereospecific reduction of sapogen-3-ones |
| CN103044513A (en) * | 2012-12-20 | 2013-04-17 | 湖北省丹江口开泰激素有限责任公司 | Method for manufacturing dehydropregnenolone acetate by using mixed solvent |
-
2016
- 2016-11-29 CN CN201611073481.4A patent/CN106810592A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004037845A1 (en) * | 2002-10-28 | 2004-05-06 | Phytopharm Plc | Stereospecific reduction of sapogen-3-ones |
| CN103044513A (en) * | 2012-12-20 | 2013-04-17 | 湖北省丹江口开泰激素有限责任公司 | Method for manufacturing dehydropregnenolone acetate by using mixed solvent |
Non-Patent Citations (3)
| Title |
|---|
| BOGDAN A.SOLAJA等: "Oxidation of steroidal 5-en-3-beta-ols with Jones reagent in ether", 《STEROIDS》 * |
| KHALED Q. SHAWAKFEH等: "Synthesis of bis-diosgenin pyrazine dimers:New cephalostatin analogs", 《STEROIDS》 * |
| ROMO, J.等: "Steroids. LV. Steroidal sapogenins. XXXV.Chemical introduction of the 6b-hydroxy group into steroidal D4-3-ketones by a two step sequence", 《JOURNAL OF ORGANIC CHEMISTRY》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105420488A (en) | Method for preprocessing wrapped uranium-molybdenum ores through oxidizing roasting | |
| CN102816093B (en) | Method for producing dimethyl disulfide by using methyl mercaptan oxidation method | |
| EA201990607A1 (en) | METHOD FOR PRODUCING A TITANIUM ALLOY BASED ON RESTORING A SELF-SPREADING ALUMINUM THERMAL GRADIENT AND SLAG REFINING | |
| CN106830073A (en) | Titanium white waste acid leaches the method that titanium slag prepares synthetic rutile | |
| CN106810592A (en) | A kind of synthesis technique of the diketone steroidal of 4 alkene 3,6 | |
| PH12016502049B1 (en) | Method for producing nickel powder having low carbon concentration and low sulfur concentration | |
| CN110656253A (en) | Method for recovering nickel hydroxide | |
| ES447652A1 (en) | Production of titanium dioxide | |
| MX2019004192A (en) | Process and facility for treating produced water from an oil & gas field. | |
| CN109402389B (en) | Method for treating scheelite in normal-pressure acidic system | |
| CN103787891A (en) | Production technology of synthesizing 6-bromo-2,4-dinitroaniline | |
| CN112609202B (en) | Method for synthesizing natural product Xanthoisozoline B through electrocatalysis and product thereof | |
| ES275828A1 (en) | Procedure for the preparation of testosterone hexahidrobencilcarbonate (Machine-translation by Google Translate, not legally binding) | |
| CN109205614A (en) | A kind of preparation method of ultra-fine powerful expansible graphite | |
| CN104278164B (en) | Grade is at the fluorine carbonated rare earth ore deposit of 62%-72% treatment process | |
| MX2021007012A (en) | Recovery of gold and silver values from feedstocks using ultrasound-assisted extraction. | |
| CN105622702A (en) | Preparation method of ulipristal acetate key intermediate | |
| CN108623464A (en) | A kind of synthetic method of antagonist pharmaceuticals intermediate o-nitrobenzoic acid | |
| CN108118346A (en) | High tenacity gold article fabrication methods | |
| CN108238952A (en) | The synthetic method of organic synthesis intermediate 4- nitro -1,8- naphthalenedicarboxylic acids | |
| NZ757065A (en) | Method of treating titanium-containing slag | |
| CN108395388A (en) | A kind of synthetic method of organic synthesis intermediate metanilic acid | |
| CN110862081A (en) | Method for reducing graphene by hydrazine hydrate | |
| ES246821A1 (en) | Improvements related to the manufacture of hydrogen peroxide (Machine-translation by Google Translate, not legally binding) | |
| CN105503772A (en) | Preparation method for N-tert-butyl benzothiazole sulfenamide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170609 |
|
| RJ01 | Rejection of invention patent application after publication |