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Synthesis method of cinnamate, cinnamonitrile, cinnamamide and derivative thereof

A technology of cinnamic amide and cinnamic acid ester, which is applied in the field of synthesis of cinnamic acid compounds, and achieves the effects of high product yield, simple operation and mild reaction conditions

Inactive Publication Date: 2013-07-24
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Disadvantages of this reaction: 1,3-bis(diphenylphosphine)propane, which is sensitive to air and toxic, is used as ligand, and the reaction time takes 20 hours
The disadvantage of this method is that it is only suitable for methyl acrylate (Adv.Synth.Catal.2010, 352, 2463)

Method used

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  • Synthesis method of cinnamate, cinnamonitrile, cinnamamide and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Taking the preparation of ethyl cinnamate as an example, its structural formula is shown in formula VI, where R 3 , R 4 , R 5 , R 6 , R 7 are hydrogen, R 8 for-COOC 2 h 5 , the raw materials used and the preparation method thereof are as follows:

[0022]

[0023] Add 5.6mg (0.025mmol) palladium acetate and 6.0mg (0.025mmol) 1,2-di-tert-butyl sulfoxide ethane into a 25mL reaction tube, add 1.3g (1mL) dichloromethane, palladium acetate and dichloromethane The mass ratio is 1:232, heated to 45°C, stirred at constant temperature for 5 hours, dichloromethane was distilled off under reduced pressure, and vacuum dried at 35°C for 5 hours to prepare a catalyst.

[0024] Add 53.5mg (0.125mol) tetraphenyltin, 127mg (1mmol) silver fluoride, 100mg (1mmol) ethyl acrylate to 11.6mg (0.025mol) catalyst, catalyst and tetraphenyltin, ethyl acrylate, fluoride The molar ratio of silver is 0.2:1:8:8, inject 2.1g (2mL) of glacial acetic acid with a syringe, the mass ratio of tet...

Embodiment 2

[0026] Taking the preparation of ethyl 4-methoxycinnamate as an example, its structural formula is shown in formula VI, where R 3 , R 4 , R 6 , R 7 are hydrogen, R 5 is methoxy, R 8 for-COOC 2 h 5 , the raw materials used and the preparation method thereof are as follows:

[0027] In Example 1, the tetraphenyltin used is replaced with equimolar 4-methoxytetraphenyltin, and other steps are the same as in Example 1 to prepare ethyl 4-methoxycinnamate, and its yield is 75%, the spectral data of the product is: 1 H NMR (300MHz, CDCl 3 )δ(ppm):7.57(d,J=15.0Hz,1H),7.40(d,J=8.4Hz,2H),6.83(d,J=8.4Hz,2H),6.24(d,J=15.0Hz ,1H),4.18(q,J=7.2Hz,2H),3.76(s,3H),1.26(t,J=7.2Hz,2H); 13 C NMR (75MHz, CDCl 3)δ (ppm): 166.9, 161.0, 143.8, 131.6, 128.6, 126.9, 115.5, 114.059.9, 54.9, 13.9.

Embodiment 3

[0029] Taking the preparation of ethyl 4-fluorocinnamate as an example, its structural formula is shown in formula VI, where R 3 , R 4 , R 6 , R 7 are hydrogen, R 5 is fluorine, R 8 for-COOC 2 h 5 , the raw materials used and the preparation method thereof are as follows:

[0030] In Example 1, the tetraphenyltin used was replaced with equimolar 4-fluorotetraphenyltin, and the other steps were the same as in Example 1 to prepare ethyl 4-fluorocinnamate with a yield of 85%, the product The spectral data of is: 1 H NMR (300MHz, CDCl 3 )δ(ppm):7.56(d,J=15.0Hz,1H),7.45-7.40(m,2H),7.02-6.96(m,2H),6.27(d,J=15.0Hz,1H),4.20( q,J=7.2Hz,2H),1.26(t,J=7.2Hz,3H); 13 C NMR (75MHz, CDCl 3 )δ (ppm): 166.0, 164.6, 161.3, 142.3, 129.8, 129.0, 128.9, 117.2, 117.1, 115.2, 114.9, 59.6, 13.4.

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Abstract

The invention discloses a synthesis method of cinnamate, cinnamonitrile, cinnamamide and derivative thereof. According to the synthesis method, the cheap and easily-available, non-toxic or low-toxicity and high-stability sulfoxide compound replaces the traditional toxic phosphine ligand or imine ligand sensitive to air and difficult to synthesize, tetra-aryl tin is used as an arylation reagent which reacts with alkene to generate corresponding cinnamate, cinnamonitrile, cinnamamide and derivative thereof. The synthesis method disclosed by the invention has the advantages of easiness in operation, mild reaction conditions, high atom utilization rate, low production cost and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of cinnamic acid compounds, and in particular relates to a synthesis method of cinnamate, cinnamonitrile, cinnamate and derivatives thereof. Background technique [0002] Cinnamic acid and its derivatives are a class of important pharmaceutical and chemical intermediates with a wide range of sources and safety. It has been reported that it is a hormone that regulates plant growth and differentiation, and also has antimicrobial and anti-inflammatory effects. Domestic studies in recent years have shown that it has a wide range of anti-solid tumor activity. United Kingdom Unilever obtained the World Intellectual Property Organization patent PCTInt.Appl.WO 01 87,080 (2001, November 22) to introduce the composition of cinnamic acid and pasteurization additives, which have strong bactericidal and antiseptic effects. Cinnamic acid is also a component of capsaicin synthase - cinnamic acid hydrolase, wh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/00C07C67/343C07C69/618C07C69/734C07C69/65C07C253/30C07C255/34C07C255/35C07C231/12C07C233/11
Inventor 薛东范小刚肖建良王超
Owner SHAANXI NORMAL UNIV
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