Bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, methyl ester, (1R,4S)- (9CI)

Base Information

• Chemical Name: Bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, methyl ester, (1R,4S)- (9CI)
• CAS No.: 99946-16-4
• Molecular Formula: C9H10O2
• Molecular Weight: 150.1745
• Mol file: 99946-16-4.mol

Synonyms:Bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, methyl ester, (1R,4S)- (9CI)

Chemical Property of Bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, methyl ester, (1R,4S)- (9CI)

Chemical Property:

• PSA: 26.30000
• LogP: 1.29170

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, methyl ester, (1R,4S)- (9CI)

There total 8 articles about Bicyclo[2.2.1]hepta-2,5-diene-2-carboxylic acid, methyl ester, (1R,4S)- (9CI) 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: 60.0%

(1R,2R,3R,4S)-3-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester (99894-26-5) → methyl (1R)-bicyclo<2.2.1>hepta-2,5-diene-2-carboxylate (99946-16-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 3.5h; Heating;

DOI:10.1021/jo00359a014

Reference yield:

(Z)-3-((R)-2-Hydroxy-2-phenyl-ethanesulfinyl)-acrylic acid methyl ester (111536-46-0,111536-47-1) → (R)-2-methylthio-1-phenyl-ethanol (111613-52-6,94730-58-2) + (+)-2-methoxy-carbonylnorbornadiene (111613-51-5) + methyl (1R)-bicyclo<2.2.1>hepta-2,5-diene-2-carboxylate (99946-16-4)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/S0040-4039(00)95662-4

Reference yield:

(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester → methyl (1R)-bicyclo<2.2.1>hepta-2,5-diene-2-carboxylate (99946-16-4)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1248/cpb.42.854

upstream raw materials:

(Z)-3-((R)-2-Hydroxy-2-phenyl-ethanesulfinyl)-acrylic acid methyl ester

(1R,2R,3R,4S)-3-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester

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