CN110467591A - Rare earth metal complex promote one pot process cosmetic active object Bose because - Google Patents
Rare earth metal complex promote one pot process cosmetic active object Bose because Download PDFInfo
- Publication number
- CN110467591A CN110467591A CN201910785216.6A CN201910785216A CN110467591A CN 110467591 A CN110467591 A CN 110467591A CN 201910785216 A CN201910785216 A CN 201910785216A CN 110467591 A CN110467591 A CN 110467591A
- Authority
- CN
- China
- Prior art keywords
- bose
- synthesized
- rare earth
- earth metal
- xylose
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/184—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine mixed aromatic/aliphatic ring systems, e.g. indoline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
- B01J2531/35—Scandium
Abstract
The invention belongs to organic synthesis, fine chemicals, field of daily chemicals, and in particular to a kind of rare earth metal complex promote by xylose and ethyl acetoacetate one pot process Bose because method.This method is easy to operate, and reagent is cheap and easy to get, has good prospects for commercial application.
Description
Technical field
The invention belongs to organic synthesis, fine chemicals, field of daily chemicals, and in particular to a kind of rare earth metal complex
Object promote by xylose and ethyl acetoacetate one pot process Bose because method.
Background technique
Bose because also known as hydroxypropyl oxinane triol (CAS 439685-79-7) be a kind of bioactive substance, can
To be widely used in the numerous areas such as food, biology, medicine, cosmetics to symptoms such as resisting age of skin, dehydrations.For glass
Color because synthetic method, though have some document reports at present, generally require number step reaction, complex process, higher cost.This hair
It is bright provide it is a kind of using xylose and ethyl acetoacetate one pot process Bose because method.The characteristics of this method, is using one
For class rare earth metal complex as catalyst, it can promote glycosylation reaction and the catalysis of xylose and ethyl acetoacetate
The hydrolysis decarboxylation of ester group and subsequent carbonyl are by the reduction of isopropanol.This method is easy to operate, and reagent is cheap and easy to get, has good
Prospects for commercial application.
Summary of the invention
The purpose of the present invention is to provide promote in rare earth metal complex using xylose and ethyl acetoacetate as raw material
Under, one pot process Bose because method.Rare earth metal complex promotes the glycosylation of xylose and ethyl acetoacetate first
Reaction, and is catalyzed the hydrolysis decarboxylation of ester group, yet further carbonyl is promoted to be restored by isopropanol, thus be made Bose because.Specifically
The structural formula of reaction and catalyst is as follows:
In the catalyst structure of the reaction, R1, R2, R3, R4, R5, R6, R7For hydrogen atom or any identical or different
Alkyl, aryl or heterocycle.
In the catalyst structure of the reaction, [M] is the rare earth with 0~3 anion, and here
Anion includes chloride ion, bromide ion, iodide ion, trifluoromethanesulfonic acid radical ion, perchlorate, acetate ion etc., dilute
Earth metal includes scandium, iridium and group of the lanthanides and actinides atom, such as cerium, samarium, europium.
The amount of the substance of the catalyst is the 1~5% of the amount of xylose substance.
The mass ratio of the material of the ethyl acetoacetate and xylose is 1~1.2:1.
The isopropanol not only solvent as reaction, but also as the reducing agent of carbonyl, dosage be xylose quality 3~
6 times.
The reaction temperature is 80-100 degrees Celsius.
The invention has the benefit that
The present invention provides a kind of promotions of rare earth metal complex by xylose and ethyl acetoacetate one pot process glass
Color because method.This method is easy to operate, and reagent is cheap and easy to get, green safe, high-efficiency environment friendly, is suitable for industrialized production.
Specific embodiment
Embodiment one:
150 grams of isopropanol, 30 grams of xylose (0.2mol), 1.2 grams of catalyst are sequentially added in the reaction flask of 500ml
(0.002 mol) after reacting 36 hours under 26 grams of ethyl acetoacetate (0.2mol), 80 degrees Celsius, is extracted with water and ethyl acetate
Take removing water layer three times, organic layer anhydrous sodium sulfate drying.Solvent is removed with Rotary Evaporators, obtains 32.5 Ke Boseyin,
Yield 85%.
Embodiment two:
150 grams of isopropanol, 30 grams of xylose (0.2mol), 1.3 grams of catalyst are sequentially added in the reaction flask of 500ml
(0.002 mol) after reacting 36 hours under 26 grams of ethyl acetoacetate (0.2mol), 80 degrees Celsius, is extracted with water and ethyl acetate
Take removing water layer three times, organic layer anhydrous sodium sulfate drying.Solvent is removed with Rotary Evaporators, obtains 31.2 Ke Boseyin,
Yield 81%.
Claims (7)
1. one kind using xylose and ethyl acetoacetate as raw material, rare earth metal complex promotion under, one pot process Bose because
Method, specific reaction such as the following figure:
2. according to claim 1 synthesized Bose because method, which is characterized in that it is described to react the catalyst structure used
In, R1, R2, R3, R4, R5, R6, R7For hydrogen atom or any identical or different alkyl, aryl or heterocycle.
3. according to claim 1 synthesized Bose because method, which is characterized in that it is described to react the catalyst structure used
In, [M] be the rare earth with 0~3 anion, and anion here include chloride ion, bromide ion, iodine from
Son, trifluoromethanesulfonic acid radical ion, perchlorate, acetate ion etc., rare earth metal include scandium, iridium and group of the lanthanides and actinium series member
Plain atom, such as cerium, samarium, europium.
4. according to claim 1 synthesized Bose because method, which is characterized in that the amount of the substance of the catalyst is wood
The 1~5% of the amount of sugar substance.
5. according to claim 1 synthesized Bose because method, which is characterized in that the ethyl acetoacetate and xylose
The mass ratio of the material be 1~1.2:1.
6. according to claim 1 synthesized Bose because method, which is characterized in that the isopropanol is both as reacting
Solvent, and the reducing agent as carbonyl, dosage are 3~6 times of xylose quality.
7. according to claim 1 synthesized Bose because method, which is characterized in that the reaction temperature is that 80-100 is Celsius
Degree.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910785216.6A CN110467591A (en) | 2019-08-23 | 2019-08-23 | Rare earth metal complex promote one pot process cosmetic active object Bose because |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910785216.6A CN110467591A (en) | 2019-08-23 | 2019-08-23 | Rare earth metal complex promote one pot process cosmetic active object Bose because |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110467591A true CN110467591A (en) | 2019-11-19 |
Family
ID=68513648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910785216.6A Pending CN110467591A (en) | 2019-08-23 | 2019-08-23 | Rare earth metal complex promote one pot process cosmetic active object Bose because |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110467591A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111529453A (en) * | 2020-06-15 | 2020-08-14 | 北京旋光普利生物医药科技开发有限公司 | Preparation of anti-aging hydrolat toner (toning lotion) |
| CN111559998A (en) * | 2020-05-20 | 2020-08-21 | 铭颜生物科技(广州)有限公司 | Synthesis method of hydroxypropyl tetrahydropyrane triol |
| CN111635401A (en) * | 2020-06-18 | 2020-09-08 | 镇江卡博医药科技有限公司 | Copper complex promoted 7-fluoroimidazo [1,2-a ] pyridine synthesis method |
| CN111704595A (en) * | 2020-07-01 | 2020-09-25 | 江苏瑞蓓丽生物科技有限公司 | Method for separating and purifying vitronectin from enzyme reaction liquid |
| CN111876452A (en) * | 2020-07-01 | 2020-11-03 | 江苏瑞蓓丽生物科技有限公司 | Method for preparing vitronectin by biological enzyme one-pot method |
| CN112321541A (en) * | 2020-12-08 | 2021-02-05 | 南京先之达医药科技有限公司 | Synthesis method of hydroxypropyl tetrahydrofuran |
| CN113135882A (en) * | 2021-04-09 | 2021-07-20 | 海南夸克科技有限公司 | Method for synthesizing vitronectin by one-pot method |
| CN113173900A (en) * | 2021-04-09 | 2021-07-27 | 海南夸克科技有限公司 | Synthetic method of vitreous chromogen |
| CN113416756A (en) * | 2021-07-12 | 2021-09-21 | 上海克琴科技有限公司 | Method for synthesizing hydroxypropyl tetrahydropyrane triol catalyzed by biological enzyme |
| CN113735811A (en) * | 2021-11-03 | 2021-12-03 | 深圳瑞德林生物技术有限公司 | Method for synthesizing vitrochromic factor through acylation protection and reduction |
| CN113735810A (en) * | 2021-11-03 | 2021-12-03 | 深圳瑞德林生物技术有限公司 | Method for synthesizing vitronectin through protection and reduction of acetal/ketal |
| CN114835666A (en) * | 2022-06-30 | 2022-08-02 | 天津泰普制药有限公司 | Continuous synthesis method of hydroxypropyl tetrahydropyrane triol |
| CN115197186A (en) * | 2021-04-12 | 2022-10-18 | 中国科学院大连化学物理研究所 | Preparation method of biomass-based pyranoside derivative |
| CN115197282A (en) * | 2021-04-12 | 2022-10-18 | 中国科学院大连化学物理研究所 | Preparation method of pyranoside derivative |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060223763A1 (en) * | 2000-12-22 | 2006-10-05 | L'oreal S.A. | C-glycoside compounds for stimulating the synthesis of glycosaminoglycans |
| CN102040575A (en) * | 2009-10-14 | 2011-05-04 | 北京和诚先锋医药技术有限公司 | Method for preparing C-glucoside derivatives |
-
2019
- 2019-08-23 CN CN201910785216.6A patent/CN110467591A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060223763A1 (en) * | 2000-12-22 | 2006-10-05 | L'oreal S.A. | C-glycoside compounds for stimulating the synthesis of glycosaminoglycans |
| CN102040575A (en) * | 2009-10-14 | 2011-05-04 | 北京和诚先锋医药技术有限公司 | Method for preparing C-glucoside derivatives |
Non-Patent Citations (2)
| Title |
|---|
| ALEXANDRE CAVEZZA等: "Synthesis of Pro-Xylane:A new biologically active C-glycoside in aqueous media", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 * |
| 黄冬婷等: "玻色因的合成", 《广东化工》 * |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111559998A (en) * | 2020-05-20 | 2020-08-21 | 铭颜生物科技(广州)有限公司 | Synthesis method of hydroxypropyl tetrahydropyrane triol |
| CN111529453A (en) * | 2020-06-15 | 2020-08-14 | 北京旋光普利生物医药科技开发有限公司 | Preparation of anti-aging hydrolat toner (toning lotion) |
| CN111635401A (en) * | 2020-06-18 | 2020-09-08 | 镇江卡博医药科技有限公司 | Copper complex promoted 7-fluoroimidazo [1,2-a ] pyridine synthesis method |
| CN111704595A (en) * | 2020-07-01 | 2020-09-25 | 江苏瑞蓓丽生物科技有限公司 | Method for separating and purifying vitronectin from enzyme reaction liquid |
| CN111876452A (en) * | 2020-07-01 | 2020-11-03 | 江苏瑞蓓丽生物科技有限公司 | Method for preparing vitronectin by biological enzyme one-pot method |
| CN112321541A (en) * | 2020-12-08 | 2021-02-05 | 南京先之达医药科技有限公司 | Synthesis method of hydroxypropyl tetrahydrofuran |
| CN112321541B (en) * | 2020-12-08 | 2023-03-28 | 南京先达医药科技有限公司 | Synthesis method of hydroxypropyl tetrahydropyrane triol |
| CN113135882A (en) * | 2021-04-09 | 2021-07-20 | 海南夸克科技有限公司 | Method for synthesizing vitronectin by one-pot method |
| CN113173900A (en) * | 2021-04-09 | 2021-07-27 | 海南夸克科技有限公司 | Synthetic method of vitreous chromogen |
| CN115197186A (en) * | 2021-04-12 | 2022-10-18 | 中国科学院大连化学物理研究所 | Preparation method of biomass-based pyranoside derivative |
| CN115197186B (en) * | 2021-04-12 | 2024-04-16 | 中科催化新技术(大连)股份有限公司 | Preparation method of biomass-based pyranoside derivative |
| CN115197282A (en) * | 2021-04-12 | 2022-10-18 | 中国科学院大连化学物理研究所 | Preparation method of pyranoside derivative |
| CN113416756A (en) * | 2021-07-12 | 2021-09-21 | 上海克琴科技有限公司 | Method for synthesizing hydroxypropyl tetrahydropyrane triol catalyzed by biological enzyme |
| CN113416756B (en) * | 2021-07-12 | 2023-10-31 | 上海克琴科技有限公司 | Method for synthesizing hydroxypropyl tetrahydropyran triol catalyzed by biological enzyme |
| CN113735810B (en) * | 2021-11-03 | 2022-02-25 | 深圳瑞德林生物技术有限公司 | Method for synthesizing vitronectin through protection and reduction of acetal/ketal |
| CN113735811B (en) * | 2021-11-03 | 2022-02-08 | 深圳瑞德林生物技术有限公司 | Method for synthesizing vitrochromic factor through acylation protection and reduction |
| CN113735810A (en) * | 2021-11-03 | 2021-12-03 | 深圳瑞德林生物技术有限公司 | Method for synthesizing vitronectin through protection and reduction of acetal/ketal |
| CN113735811A (en) * | 2021-11-03 | 2021-12-03 | 深圳瑞德林生物技术有限公司 | Method for synthesizing vitrochromic factor through acylation protection and reduction |
| CN114835666A (en) * | 2022-06-30 | 2022-08-02 | 天津泰普制药有限公司 | Continuous synthesis method of hydroxypropyl tetrahydropyrane triol |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110467591A (en) | Rare earth metal complex promote one pot process cosmetic active object Bose because | |
| CN113135882A (en) | Method for synthesizing vitronectin by one-pot method | |
| CN111689878A (en) | Preparation process of trifluoromethanesulfonic anhydride | |
| CN105949240A (en) | Method for synthesizing 4-phosphonic acid-1,5-substituted-1,2,3 triazole compounds through catalysis of ionic liquid | |
| CN102180914A (en) | Preparation method of 2-deoxidizing-D-glucose | |
| CN105330560A (en) | Enzalutamide intermediate preparation method | |
| CN103145636B (en) | 1,4-diacyl-3,6-diphenyl-1,4-dihydrotetrazine compound as well as preparation method and application thereof | |
| CN105399667A (en) | Preparation method of edoxaban intermediate | |
| CN102746235B (en) | Improved method for preparing imidafenacin | |
| CN109134331B (en) | Synthesis method of azithromycin genotoxic impurity | |
| CN104402865B (en) | A kind of preparation method of esomeprazole magnesium addition D | |
| CN103709209A (en) | Isopropyl-beta-D-thiogalactoside preparation method | |
| CN111747876B (en) | Method for preparing astaxanthin by oxidizing canthaxanthin | |
| CN108752399B (en) | Synthesis method of isopropyl-beta-D-thiogalactoside | |
| CN100412071C (en) | High purity delta-alpha-tocopherol succinic acid monoester preparation method | |
| CN102924540A (en) | Preparation method of 2-deoxy-D-glucose | |
| CN102993256B (en) | The trimethyl silicon based method in uncle position that the complete trimethyl silicon based protection of a kind of selectively removing is sugared | |
| CN104496900A (en) | Method for preparing 2-methoxy-6-one-5,7,8-trihydro-quinoline | |
| CN105801529B (en) | A kind of preparation method of carbonic acid linalool oxide (pyranoid form and furan type) ester ethyl ester | |
| CN103073481A (en) | Preparation method for 4-azaspiro [2.4] heptane hydrochloride | |
| CN110354902B (en) | Process for preparing phosphine guanidine compound | |
| CN105037348B (en) | A kind of Retapamulin synthetic method | |
| CN105330704A (en) | Preparation method of 2-deoxy-D-glucose | |
| CN116082111B (en) | Method for synthesizing 1, 2-triarylethane | |
| CN103694285B (en) | A kind of preparation method of isopropyl-β-D-thiogalactoside(IPTG) |
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 | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20191119 |