CN103497103A - Method for synthesizing trans-acetoxyl cinnamic acid derivative in one step by utilizing hydroxy benzaldehyde derivative - Google Patents

Method for synthesizing trans-acetoxyl cinnamic acid derivative in one step by utilizing hydroxy benzaldehyde derivative Download PDF

Info

Publication number
CN103497103A
CN103497103A CN201310460954.6A CN201310460954A CN103497103A CN 103497103 A CN103497103 A CN 103497103A CN 201310460954 A CN201310460954 A CN 201310460954A CN 103497103 A CN103497103 A CN 103497103A
Authority
CN
China
Prior art keywords
formula
hydroxy benzaldehyde
derivative shown
acetoxyl
cinnamic acid
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
Application number
CN201310460954.6A
Other languages
Chinese (zh)
Inventor
夏春年
陈友宝
薛凌霄
严强强
高建荣
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhejiang University of Technology ZJUT
Original Assignee
Zhejiang University of Technology ZJUT
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Zhejiang University of Technology ZJUT filed Critical Zhejiang University of Technology ZJUT
Priority to CN201310460954.6A priority Critical patent/CN103497103A/en
Publication of CN103497103A publication Critical patent/CN103497103A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a method for synthesizing trans-acetoxyl cinnamic acid derivative shown in a formula (II) in one step by utilizing hydroxy benzaldehyde derivative shown in a formula (I). The method for synthesizing the trans-acetoxyl cinnamic acid derivative shown in the formula (II) in one step by utilizing hydroxy benzaldehyde derivative shown in the formula (I) comprises the following steps: carrying out a reflux reaction on the hydroxy benzaldehyde derivative shown in the formula (I) in acetic anhydride under the action of a catalyst, cooling after the reflux reaction is complete, and carrying out aftertreatment on a reaction liquid to obtain the trans (E) acetoxyl cinnamic acid derivative shown in the formula (II), wherein the catalyst is weak acid strong base salt and/or weak organic base; in the formula (I), R1-R5 are respectively selected from hydroxyl, C1-C2 alkoxy, nitryl, chlorine or bromine, and at least one of R1-R5 is hydroxyl; in the formula (II), R'1-R'5 correspond to R1-R5 in the formula (I), all the groups remain unchanged except that hydroxyl is changed into an acetoxyl group. The method for synthesizing the trans-acetoxyl cinnamic acid derivative shown in the formula (II) in one step by utilizing hydroxy benzaldehyde derivative shown in the formula (I) has the advantages of mild reaction conditions, high product purity, low cost, short reaction period and easy operation.

Description

A kind of method by the trans acetoxyl group cinnamic acid derivative of hydroxy benzaldehyde derivative one-step synthesis
(1) technical field
The present invention relates to a kind of method by the trans acetoxyl group cinnamic acid derivative of hydroxy benzaldehyde derivative one-step synthesis, the Perkin reaction that particularly relates to the protective reaction of phenolic hydroxyl group and prepare cinnamic acid derivative.
(2) background technology
Hydroxy cinnamic acid derivative is all important source material and the intermediate of pharmaceutical prod as p-Coumaric Acid, forulic acid, coffic acid etc.
The hydroxycinnamic acid compound mainly extensively is present in plant materials with the form of organic acid acetic and polysaccharide glycosides as p-Coumaric Acid, forulic acid, coffic acid etc., and they have larger impact to character such as the stability of food, color and luster, smell, nutrition.Hydroxy cinnamic acid derivative has the ability of clear and definite and relatively powerful removing hydroxyl radical free radical (OH), and the pathology that some free radicals are caused and damage have good prevention and provide protection.The hydroxyl radical free radical that cell produces in the aerobic metabolism process (OH) be the most active in active oxygen radical, that toxicity is the strongest is a kind of, can produce and can directly cause the destruction of the biomacromolecules such as DNA to cause a series of diseases by number of ways.
In addition, when styracin and derivative thereof make them as the makeup whitening additive to the retarding effect of tyrosine oxidase, can effectively suppress the activity of skin tyrosine oxidase, prevent that skin is because being subject to the uviolizing brown stain.Due to the existence that phenolic hydroxyl group is arranged, the hydroxyl in synthetic, as to produce hydroxycinnamic acid and derivative thereof process on self phenyl ring is easily oxidized and colour-change phenomena occurs, or is reacted away.When hydroxycinnamic acid and derivative thereof participate in some reaction as raw material, often need hydroxyl is protected remove-insurance again after relevant building-up reactions finishes.Increase by two reactions of hydroxyl protection and deprotection in reaction process, greatly reduced reaction process Atom utilization ratio.
(3) summary of the invention
What the invention provides that a kind of reaction conditions is gentle, product purity is high, cost is low, reaction time is short, easy and simple to handle directly prepares the acetoxyl group cinnamic acid derivative from corresponding hydroxy benzaldehyde derivative one step, has protected phenolic hydroxyl group when preparing cinnamic acid derivative.
The technical solution used in the present invention is as follows:
A kind of by shown in the hydroxy benzaldehyde derivative one-step synthesis formula (II) shown in formula (I) the method for trans acetoxyl group cinnamic acid derivative, it comprises: the hydroxy benzaldehyde derivative shown in formula (I) in diacetyl oxide under catalyst action back flow reaction, react completely rear cooling, reaction solution obtains the trans acetoxyl group cinnamic acid derivative shown in formula (II) through aftertreatment; Described catalyzer is weak acid strong alkali salt and/or weak property organic bases;
Figure BDA0000390551680000021
In formula (I), R 1-R 5independently be selected from separately hydrogen, hydroxyl, C 1～C 2alkoxyl group, nitro, chlorine or bromine, and R 1-R 5in have one at least for hydroxyl; In formula (II), R ' 1-R ' 5with the R in formula (I) 1-R 5corresponding one by one, except hydroxyl wherein becomes acetoxyl group, all the other corresponding groups all remain unchanged.
In the present invention, described catalyzer is weak acid strong alkali salt and/or weak property organic bases, and wherein weak acid strong alkali salt can be selected from following a kind of or several combination arbitrarily: sodium-acetate, Potassium ethanoate, sodium carbonate, salt of wormwood, sodium bicarbonate, saleratus; Described weak property organic bases can be selected from following a kind of or several combination arbitrarily: pyridine, piperidines, pyrazoles.Further, preferably one of following or several combination arbitrarily of described catalyzer: salt of wormwood, sodium carbonate, sodium-acetate, Potassium ethanoate, pyridine, piperidines, pyrazoles.Further, described catalyzer sodium-acetate most preferably.The mol ratio of described catalyzer and hydroxy benzaldehyde derivative is 0.1～3:1, is preferably 1～2:1.
In the present invention, described diacetyl oxide is both as solvent, and again as reactant, the mol ratio of described diacetyl oxide and hydroxy benzaldehyde derivative is 5～50:1, is preferably 5～15:1.
Reaction of the present invention is carried out under reflux temperature, and the reaction times is generally at 6～24 hours, preferably 9～12 hours.
Aftertreatment of the present invention is conventional aftertreatment, those skilled in the art can select suitable post-treating method voluntarily according to product characteristics, such as can first joining cooled reaction solution in suitable quantity of water, putting into refrigerator freezing after stirring and evenly mixing spends the night, separate out solid, 95% ethanol is washed, and washing is dried and is product.Also can join reaction solution in suitable quantity of water and use the organic solvent extractions such as ethyl acetate, ether after stirring and evenly mixing for another example, extraction liquid obtains crude product except after desolventizing, and crude product obtains product with ethanol or Gossypol recrystallized from chloroform.
Compared with prior art, beneficial effect of the present invention is: the present invention has protected phenolic hydroxyl group when utilizing Perkin reaction to prepare styracin, one-step synthesis the acetoxyl group cinnamic acid derivative; easy and simple to handle, reaction time is short, the reaction conditions gentleness; product purity is high, and cost is low.
(4) embodiment
Below with specific embodiment, technical scheme of the present invention is described further, but protection scope of the present invention is not limited to this:
Embodiment mono-
The preparation of 4-acetoxyl group forulic acid
Figure BDA0000390551680000031
Add successively vanillin food grade,1000.000000ine mesh (3g, 19Mmol), sodium acetate, anhydrous (2.5g, 30Mmol) and diacetyl oxide (20ml, 200Mmol) in the 50ml round-bottomed bottle, back flow reaction 9h.Naturally be chilled to room temperature, slowly go in 100ml water, after stirring and evenly mixing, refrigerator freezing obtains buff powder, and 95% ethanol is washed, and 3.6g acetoxyl group forulic acid (yield 79%) is dried to obtain in washing.HPLC:97.9%(chromatographic column: IBM-C 18post, moving phase: acetonitrile: 0.5% acetic acid=28:72, λ=322nm, flow velocity 1.0mL/min, 25 ℃ of column temperatures)
Fusing point: 183-185 ℃.
IR(KBr)，cm -1：3011,2943,2845,1689,1632。
1H?NMR（DMSO-D 6），δ ppm:12.35(s,1H,COOH),7.56(d,J=15.9Hz,1H,α-H),7.46(d,J=1.7Hz,1H,Ar-H)，7.24(dd,J=8.2,1.7Hz,1H,Ar-H)，7.09(d,J=8.2Hz,1H,Ar-H)，6.56(d,J=16.0Hz,1H,β-H),3.80(s,3H,COCH 3)，2.24(s,3H,OCH 3)。
Embodiment bis-
Make catalyzer with 1 equivalent anhydrous sodium acetate and repeat embodiment mono-, all the other conditions are identical with embodiment mono-, yield 80.5%.HPLC:96.3%(chromatographic column: IBM-C 18post, moving phase: acetonitrile: 0.5% acetic acid=28:72, λ=322nm, flow velocity 1.0mL/min, 25 ℃ of column temperatures)
Embodiment tri-
Make catalyzer with 0.5 equivalent anhydrous sodium acetate and repeat embodiment mono-, all the other conditions are identical with embodiment mono-, yield 65.3%.HPLC:99.1%(chromatographic column: IBM-C 18post, moving phase: acetonitrile: 0.5% acetic acid=28:72, λ=322nm, flow velocity 1.0mL/min, 25 ℃ of column temperatures)
Embodiment tetra-
With sodium carbonate (1 equivalent), replace the anhydrous sodium acetate in embodiment mono-to repeat embodiment mono-, all the other conditions are identical with embodiment mono-, and the product color is darker, and ethyl alcohol recrystallization obtains product, yield 45.2%.
Embodiment five
With salt of wormwood (1 equivalent), replace the anhydrous sodium acetate in embodiment mono-to repeat embodiment mono-, all the other conditions are identical with embodiment mono-, and the product color is darker, and ethyl alcohol recrystallization obtains product, yield 55.9%
Embodiment six
With pyridine (1 equivalent), replace the anhydrous sodium acetate in embodiment mono-to repeat embodiment mono-, all the other conditions are identical with embodiment mono-, and the product color is darker, and ethyl alcohol recrystallization obtains product, yield 30%.
Embodiment seven
Preparation to the acetoxyl group styracin
Figure BDA0000390551680000051
Add successively p-Hydroxybenzaldehyde (5g, 40Mmol), sodium acetate, anhydrous (6.6g, 80Mmol) and diacetyl oxide (50ml, 500Mmol) in the 50ml round-bottomed bottle, back flow reaction 5h.Naturally be chilled to room temperature, slowly go in water (100ml), ethyl acetate extraction after stirring and evenly mixing, except Gossypol recrystallized from chloroform after desolventizing obtains product (4.3g, 52.1%).
Fusing point: 202-205 ℃.
IR(KBr)，cm -1：3010,2951,1764,1701。
1H?NMR（DMSO-D 6），δ ppm:12.2(s,1H,COOH),7.62(d,J=8.7Hz,2H,Ar-H),7.55(d,J=16.0Hz,1H,α-H),6.96(d,J=8.7Hz,2H,Ar-H),6.37(d,J=16.0Hz,1H,β-H),3.78(s,3H,COCH 3)。
Embodiment eight
The preparation of 2-nitro-4-acetoxyl group forulic acid
Figure BDA0000390551680000052
Condition is identical with embodiment seven, crude product recrystallization yield 86.2%.
Fusing point: 162-163 ℃.
IR(KBr)，cm -1：2958,2694,1762,1702,1638。
1H?NMR（DMSO-D 6），δ ppm:7.83(d,J=8.7Hz,1H,Ar-H)，7.54(d,J=8.7Hz,1H,Ar-H)，7.2(d,J=15.8Hz,1H,α-H),6.67(d,J=15.8Hz,1H,β-H),3.87(s,3H,COCH 3)，2.38(s,3H,OCH 3)。
Embodiment nine
The preparation of 5-nitro-4-acetoxyl group forulic acid
Condition is identical with embodiment seven, crude product recrystallization yield 89.2%.
Fusing point: 209-211 ℃
IR(KBr)，cm -1：3083，2850，1691，1675，1637。
1H?NMR（DMSO-D 6），δ ppm:12.59(s,1H,COOH),7.98(d,J=1.8Hz,1H,Ar-H),7.87(d,J=2.2Hz,H,Ar-H),7.64(d,J=16.0Hz,1H,α-H),6.78(d,J=16.0Hz,1H,β-H),3.94(s,3H,COCH 3)，2.34(s,3H,OCH 3)。
Embodiment ten
The preparation of the bromo-4-acetoxyl group of 5-forulic acid
Figure BDA0000390551680000062
Condition is identical with embodiment seven, crude product recrystallization yield 50.2%.
Fusing point: 207-209 ℃.
IR(KBr)，cm -1：3000,2941,1690,1636,1428,1200。
1H?NMR（DMSO-D 6），δ ppm:12.45(s,1H,COOH)，7.63(d,J=1.6Hz,1H,Ar-H),7.52(d,J=1.6Hz,1H,Ar-H),7.56(d,J=16.0Hz,1H,α-H),6.68(d,J=16.0Hz,1H,β-H),3.85(s,3H,COCH 3)，2.35(s,3H,OCH 3)。
Embodiment 11
The preparation of the bromo-4-acetoxyl group of 6-forulic acid
Figure BDA0000390551680000071
Condition is identical with embodiment mono-, yield 85.2%.HPLC:95.2%(chromatographic column: IBM-C 18post, moving phase: acetonitrile: 0.5% acetic acid=28:72, λ=322nm, flow velocity 1.0mL/min, 25 ℃ of column temperatures)
Fusing point: 212-215 ℃.
IR(KBr)，cm -1：3004，2942，2854，1691，1629。
1H?NMR（CDCl 3），δ ppm:8.10(d,J=15.9Hz,1H,α-H),7.34(s,,Ar-H)，7.17(s,1H,Ar-H),6.36(d,J=15.9Hz,1H,β-H),3.88(s,3H,COCH 3)，2.34(s,3H,OCH 3)。
Embodiment 12
The caffeinic preparation of 3,4-diacetoxy
Figure BDA0000390551680000072
Condition is identical with embodiment mono-, yield 76.1%.HPLC:99.2%(chromatographic column: IBM-C 18post, moving phase: acetonitrile: 0.5% acetic acid=28:72, λ=322nm, flow velocity 1.0mL/min, 25 ℃ of column temperatures)
Fusing point: 134-135 ℃.
IR(KBr)，cm -1：3100-3000,2993，1689，1630,1433。
1H?NMR（DMSO-D 6），δ ppm:7.73(d,J=15.8Hz,1H,α-H),7.44(dd,J=8.5,1.8Hz,1H,Ar-H)，7.41(d,J=1.8Hz,1H,Ar-H)，7.26(d,J=8.5Hz,1H,Ar-H)，6.41(d,J=15.8Hz,1H,β-H),2.32(s,3H,COCH 3)，2.31(s,3H,COCH 3)。
Embodiment 13
5-is chloro-3, the caffeinic preparation of 4-diacetoxy
Figure BDA0000390551680000081
Condition is identical with embodiment mono-, yield 14.9%.HPLC:88.8%(chromatographic column: IBM-C 18post, moving phase: acetonitrile: 0.5% acetic acid=28:72, λ=322nm, flow velocity 1.0mL/min, 25 ℃ of column temperatures)
Fusing point: 144-148 ℃
IR(KBr)，cm -1：3100-3000,2935，1695，1637，1429。
1H?NMR（DMSO-D 6），δppm:12.56(s,1H,COOH)，7.91(d,J=1.8Hz,1H,Ar-H)，7.71(d,J=1.8Hz,1H,Ar-H)，7.56(d,J=16.0Hz,1H,α-H)，6.64(d,J=16.0Hz,1H,β-H)，2.37(s,3H,COCH 3)，2.32(s,3H,COCH 3)。
Embodiment 14
5-is bromo-3, the caffeinic preparation of 4-diacetoxy
Figure BDA0000390551680000082
Condition is identical with embodiment mono-, yield 38.1%.HPLC:93.34%(chromatographic column: IBM-C 18post, moving phase: acetonitrile: 0.5% acetic acid=28:72, λ=322nm, flow velocity 1.0mL/min, 25 ℃ of column temperatures)
Fusing point: 202-205 ℃
IR(KBr)，cm -1：3077，3000-2800，1722，1635，1413，1195。
1H?NMR（DMSO-D 6），δppm:12.56(s,1H,COOH)，8.03(d,J=1.9Hz,1H,Ar-H)，7.74(d,J=1.9Hz,1H,Ar-H)，7.55(d,J=16.0Hz,1H,α-H)，6.63(d,J=16.0Hz,1H,β-H)，2.37(s,3H,COCH 3)，2.32(s,3H,COCH 3)。
Embodiment 15
5-nitro-3, the caffeinic preparation of 4-diacetoxy
Figure BDA0000390551680000091
Condition is identical with embodiment mono-, yield 24.3%.HPLC:75.4%(chromatographic column: IBM-C 18post, moving phase: acetonitrile: 0.5% acetic acid=28:72, λ=322nm, flow velocity 1.0mL/min, 25 ℃ of column temperatures)
Fusing point: 203-205 ℃
IR(KBr)，cm -1：3086，3000-2800，1778，1638，1430。
1H?NMR（DMSO-D 6），δppm:8.39（s,1H，Ar-H），8.16（s,1H，Ar-H），7.86(d,J=16.0Hz,1H,α-H)，6.72(d,J=16.0Hz,1H,β-H)，2.37(s,3H,COCH 3)，2.32(s,3H,COCH 3)。
Embodiment 16
6-nitro-3, the caffeinic preparation of 4-diacetoxy
Figure BDA0000390551680000092
Condition is identical with embodiment seven, crude product recrystallization yield 82.9%.
Fusing point: 170-171 ℃
IR(KBr)，cm -1：3100-3000,2991，2845，1694，1635，1429。
1H?NMR（DMSO-D 6），δppm:8.16（s,1H，Ar-H），7.87（s,1H，Ar-H），7.83(d,J=15.5Hz,1H,α-H)，6.45(d,J=15.5Hz,1H,β-H)，2.37(s,3H,COCH 3)，2.33(s,3H,COCH 3)。

Claims (8)

1. the method by the trans acetoxyl group cinnamic acid derivative shown in the hydroxy benzaldehyde derivative one-step synthesis formula (II) shown in formula (I), it comprises: the hydroxy benzaldehyde derivative shown in formula (I) in diacetyl oxide under catalyst action back flow reaction, react completely rear cooling, reaction solution obtains the trans acetoxyl group cinnamic acid derivative shown in formula (II) through aftertreatment; Described catalyzer is weak acid strong alkali salt and/or weak property organic bases;
Figure FDA0000390551670000011
In formula (I), R 1-R 5independently be selected from separately hydroxyl, C 1～C 2alkoxyl group, nitro, chlorine or bromine, and R 1-R 5in have one at least for hydroxyl; In formula (II), R ' 1-R ' 5with the R in formula (I) 1-R 5corresponding one by one, except hydroxyl wherein becomes acetoxyl group, all the other corresponding groups all remain unchanged.
2. the method for claim 1 is characterized in that: described weak acid strong alkali salt is selected from following a kind of or several combination arbitrarily: sodium-acetate, Potassium ethanoate, sodium carbonate, salt of wormwood, sodium bicarbonate, saleratus.
3. the method for claim 1 is characterized in that: described weak property organic bases is selected from following a kind of or several combination arbitrarily: pyridine, piperidines, pyrazoles.
4. the method for claim 1 is characterized in that: described catalyzer is selected from one of following or several combination arbitrarily: salt of wormwood, sodium carbonate, sodium-acetate, Potassium ethanoate, pyridine, piperidines, pyrazoles.
5. the method for claim 1, it is characterized in that: described catalyzer is sodium-acetate.
6. method as described as one of claim 1～5, it is characterized in that: the mol ratio of described catalyzer and hydroxy benzaldehyde derivative is 0.1～3:1, the mol ratio of described diacetyl oxide and hydroxy benzaldehyde derivative is 5～50:1.
7. method as claimed in claim 6, it is characterized in that: the mol ratio of described catalyzer and hydroxy benzaldehyde derivative is 1～2:1, the mol ratio of described diacetyl oxide and hydroxy benzaldehyde derivative is 5～15:1.
8. method as described as one of claim 1～5, it is characterized in that: the reaction times is 6～24 hours.
CN201310460954.6A 2013-09-29 2013-09-29 Method for synthesizing trans-acetoxyl cinnamic acid derivative in one step by utilizing hydroxy benzaldehyde derivative Pending CN103497103A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201310460954.6A CN103497103A (en) 2013-09-29 2013-09-29 Method for synthesizing trans-acetoxyl cinnamic acid derivative in one step by utilizing hydroxy benzaldehyde derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201310460954.6A CN103497103A (en) 2013-09-29 2013-09-29 Method for synthesizing trans-acetoxyl cinnamic acid derivative in one step by utilizing hydroxy benzaldehyde derivative

Publications (1)

Publication Number Publication Date
CN103497103A true CN103497103A (en) 2014-01-08

Family

ID=49862393

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201310460954.6A Pending CN103497103A (en) 2013-09-29 2013-09-29 Method for synthesizing trans-acetoxyl cinnamic acid derivative in one step by utilizing hydroxy benzaldehyde derivative

Country Status (1)

Country Link
CN (1) CN103497103A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106083561A (en) * 2016-06-07 2016-11-09 安徽圣诺贝化学科技有限公司 A kind of preparation method of sun-screening agent intermediate p-methoxycinnamic acid

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011143379A2 (en) * 2010-05-13 2011-11-17 University Of Florida Research Foundation, Inc. Poly(dihydroferulic acid) a biorenewable polyethylene terephthalate mimic derived from lignin and acetic acid

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011143379A2 (en) * 2010-05-13 2011-11-17 University Of Florida Research Foundation, Inc. Poly(dihydroferulic acid) a biorenewable polyethylene terephthalate mimic derived from lignin and acetic acid

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
LAURENT MIALON: "biorenewable polyethylene terephthalate mimics derived from lignin and acetic acid", 《GREE CHEMISTRY》 *
安悦: "其中芥子碱类似物的合成及其对家兔离体肠平滑肌张力的影响", 《药学学报》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106083561A (en) * 2016-06-07 2016-11-09 安徽圣诺贝化学科技有限公司 A kind of preparation method of sun-screening agent intermediate p-methoxycinnamic acid

Similar Documents

Publication Publication Date Title
EP1210341B1 (en) Compositions and therapeutic methods involving isoflavones and analogues thereof
AU2018383864B2 (en) Method for synthesis of Roxadustat and intermediate compounds thereof
González et al. Short syntheses of (+)-ferruginol from (+)-dehydroabietylamine
CN105218621B (en) Dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives with anti-tumor activity and preparation method therefor and application thereof
Bajwa et al. Selective deprotection of alkyl t-butyldimethylsilyl ethers in the presence of aryl t-butyldimethylsilyl ethers with bismuth bromide
CN106188190B (en) Preparation method of tolgliflozin monohydrate
Teng et al. Enantioselective synthesis of glutarimide alkaloids cordiarimides A, B, crotonimides A, B, and julocrotine
EP3643714B1 (en) 4,5-disubstituted-1-hydro-pyrrole(2,3-f)quinolone-2,7,9-tricarboxylate compound and applications
JPH08134055A (en) Production of 3-o-substituted-ascorbic acid
CN103497103A (en) Method for synthesizing trans-acetoxyl cinnamic acid derivative in one step by utilizing hydroxy benzaldehyde derivative
CN103402973B (en) Compound and production method thereof, and for the production of the method for Ro 64-0796/002
CN104909994A (en) Method for synthesizing ciprofibrate intermediate and the intermediate
CN107963976A (en) A kind of preparation method of phenyl ethyl amine compounds intermediate
CN108203396B (en) Synthesis of enkephalinase inhibitor
CN101654426B (en) Method for preparing ilomastat
CN111718264A (en) Method for co-producing 2-methyl-6-nitrobenzoic acid and 3-nitro-2-methylbenzoic acid
EP3733656B1 (en) Method for synthesis of lobaric acid and analog thereof
CN110669031B (en) Total synthesis method of natural product isoperidone J
CN101020646A (en) Synthesis process of diamino shikimate
EP4186886A1 (en) Process for the synthesis and purification of cannabinoic acids and acylated derivatives thereof
CN116162086A (en) Organic catalyst and synthetic method of stilbene derivative
CA3191689A1 (en) Synthesis method for preparing sglt inhibitor intermediate
CN101570493B (en) Preparation method of (3S, 4S)-4-amino-3-hydroxy-6-methylheptanoic acid and analogue thereof
CN105237381A (en) Preparation method of 5-hydroxy-1-indanone
CN102838653B (en) A kind of preparation method of 3-carbonyl-4-aza-5 alpha-androstane

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C05 Deemed withdrawal (patent law before 1993)
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20140108