4-Cyclohexene-1,2-dicarboxylic acid, monomethyl ester, cis-

Base Information

• Chemical Name: 4-Cyclohexene-1,2-dicarboxylic acid, monomethyl ester, cis-
• CAS No.: 31139-02-3
• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.192
• Mol file: 31139-02-3.mol

Synonyms:

Chemical Property of 4-Cyclohexene-1,2-dicarboxylic acid, monomethyl ester, cis-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Cyclohexene-1,2-dicarboxylic acid, monomethyl ester, cis-

There total 30 articles about 4-Cyclohexene-1,2-dicarboxylic acid, monomethyl ester, cis- 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: 100.0%

methanol (67-56-1) + cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) → (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid (31139-02-3,31139-03-4,56124-48-2,88335-93-7,88335-94-8,93603-11-3)

Guidance literature:

methanol; cis-1,2,3,6-tetrahydrophthalic anhydride; With quinindine; In toluene; at -55 - -18 ℃; for 80h; Inert atmosphere;

With hydrogenchloride; In water; toluene; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1039/c2cc17915f

Reference yield: 100.0%

dimethyl cyclohex-4-ene-1,2-dicarboxylate (7500-55-2) → (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid (31139-02-3,31139-03-4,56124-48-2,88335-93-7,88335-94-8,93603-11-3)

Guidance literature:

With pig liver esterase; In acetone; at 20 ℃; for 168h; pH=8; enantioselective reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1016/j.bmcl.2009.04.143

Reference yield: 99.0%

dimethyl cis-1,2,3,6-tetrahydrophthalate (4841-84-3) → (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid (31139-02-3,31139-03-4,56124-48-2,88335-93-7,88335-94-8,93603-11-3)

Guidance literature:

With sodium hydroxide; disodium hydrogenphosphate; potassium dihydrogenphosphate; pig liver esterase; at 25 ℃; for 216h;

upstream raw materials:

dimethyl cis-1,2,3,6-tetrahydrophthalate

1-methyl hydrogen 1,2-cis-1,2-cyclohex-4-ene dicarboxylate

methanol

cis-1,2,3,6-tetrahydrophthalic anhydride

Downstream raw materials:

(1R,2S)-Cyclohex-4-ene-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(1S,2R)-6-(tert-butoxycarbonyl)-3-cyclohexene-1-carboxylic acid

(1S,2R)-Cyclohex-4-ene-1,2-dicarboxylic acid di-tert-butyl ester

1-(tert-butyl) 2-methyl (1R,2S)-cyclohex-4-ene-1,2-dicarboxylate

Refernces

• 1、 Rho, Ho Sik,Oh, Sang Ho,Lee, Ji Woong,Lee, Jin Yong,Chin, Jik,Song, Choong Eui. "Bifunctional organocatalyst for methanolytic desymmetrization of cyclic anhydrides: Increasing enantioselectivity by catalyst dilution". . p. 1208 - 1210. Retrieved 2008.
• 2、 Meissner, Murray P.,Süss, Philipp,Brundiek, Henrike,Woodley, John M.,Von Langermann, Jan. "Scoping the Enantioselective Desymmetrization of a Poorly Water-Soluble Diester by Recombinant Pig Liver Esterase". . p. 1518 - 1523. Retrieved 2018.
• 3、 Goswami, Animesh,Kissick, Thomas P.. "Enzymatic desymmetrization of dimethyl cylcohex-4-ene-cis-1,2-dicarboxylate to (1S,2R)-2-(methoxycarbonyl)cyclohex-4-ene-1-carboxylic acid". . p. 483 - 488. Retrieved 2009.
• 4、 W?ltinger, Jens,Krimmer, Hans-Peter,Drauz, Karlheinz. "The potential of membrane reactors in the asymmetric opening of meso-anhydrides". . p. 8531 - 8533. Retrieved 2002.
• 5、 Chen, Lu,Liu, Da-Ming,Ma, Chao,Sun, Chen,Wang, Zhong-Hua,Xiong, Fei,Zhang, Yan-Jun,Zhu, Yi-Ren. "The New Catalyst System: Chloramphenicol Base and Organic Acid Co-catalyzed Enantioselective Alcoholysis of meso-Anhydride". . p. 9 - 13. Retrieved 2022/03/27.
• 6、 Borrmann, Ruediger,Palchyk, Volodymyr,Pich, Andrij,Rueping, Magnus. "Reversible Switching and Recycling of Adaptable Organic Microgel Catalysts (Microgelzymes) for Asymmetric Organocatalytic Desymmetrization". . p. 7991 - 7996. Retrieved 2018/09/18.