ethyl (E)-3-((1SR,2SR)-2-phenylcyclopropyl)acrylate

Base Information

• Chemical Name: ethyl (E)-3-((1SR,2SR)-2-phenylcyclopropyl)acrylate
• CAS No.: 22467-91-0
• Molecular Formula: C₁₄H₁₆O₂
• Molecular Weight: 216.28
• Mol file: 22467-91-0.mol

Synonyms:

Chemical Property of ethyl (E)-3-((1SR,2SR)-2-phenylcyclopropyl)acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (E)-3-((1SR,2SR)-2-phenylcyclopropyl)acrylate

There total 12 articles about ethyl (E)-3-((1SR,2SR)-2-phenylcyclopropyl)acrylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + rac-(1S,2R)-2-phenylcyclopropanecarbaldehyde (34271-30-2,34271-31-3,67074-44-6,79929-84-3,82263-48-7,82263-50-1) → cis-1-(trans-β-Ethoxycarbonylvinyl)-2-phenylcyclopropan (22467-91-0,37555-43-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 60 ℃; for 1.5h;

DOI:10.1021/jo970879+

Reference yield: 84.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + trans-2-phenylcyclopropanecarbaldehyde (34271-31-3) → ethyl (E)-3-((1SR,2SR)-2-phenylcyclopropyl)acrylate (22467-91-0,37555-43-4)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

trans-2-phenylcyclopropanecarbaldehyde; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/b413816n

Reference yield: 74.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + trans-2-phenylcyclopropanecarbaldehyde (34271-31-3) → ethyl (E)-3-((1SR,2SR)-2-phenylcyclopropyl)acrylate (22467-91-0,37555-43-4) + (Z)-3-((1R,2S)-2-Phenyl-cyclopropyl)-acrylic acid ethyl ester

Guidance literature:

With n-butyllithium; at 0 ℃;

DOI:10.1016/0040-4039(94)88459-5

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

(1R,2S)-1-formyl-2-phenylcyclopropane

(1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane

rac-(1S,2R)-2-phenylcyclopropanecarbaldehyde

Downstream raw materials:

6-phenylhexanoic acid ethyl ester

(2E)-6-phenylhex-2-en-1-al

6-phenylcyclohex-3-en-1-one

Refernces

• 1、 Toh, Kah Kah,Biswas, Anup,Wang, Yi-Feng,Tan, Yun Yun,Chiba, Shunsuke. "Copper-mediated oxidative transformation of N-allyl enamine carboxylates toward synthesis of azaheterocycles". . p. 6011 - 6020. Retrieved 2014/05/20.
• 2、 Barrett, Anthony G. M.,Tam, William. "Regioselective Ring Opening of Vinylcyclopropanes by Hydrogenation with Palladium on Activated Carbon". . p. 7673 - 7678. Retrieved 2007/10/03.