1-Methyl (1S,2S)-4-cyclohexene-1,2-dicarboxylate

Base Information

• Chemical Name: 1-Methyl (1S,2S)-4-cyclohexene-1,2-dicarboxylate
• CAS No.: 253454-00-1
• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.192
• DSSTox Substance ID: DTXSID001236151
• Mol file: 253454-00-1.mol

Synonyms:DTXSID001236151;1-Methyl (1S,2S)-4-cyclohexene-1,2-dicarboxylate;253454-00-1

Chemical Property of 1-Methyl (1S,2S)-4-cyclohexene-1,2-dicarboxylate

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 184.07355886
• Heavy Atom Count: 13
• Complexity: 244

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC=CCC1C(=O)O
• Isomeric SMILES: COC(=O)[C@H]1CC=CC[C@@H]1C(=O)O

Technology Process of 1-Methyl (1S,2S)-4-cyclohexene-1,2-dicarboxylate

There total 5 articles about 1-Methyl (1S,2S)-4-cyclohexene-1,2-dicarboxylate 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: 98.0%

(1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester (116733-43-8) → (1S,2S)-Cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester (253454-00-1)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 19h;

DOI:10.1021/ol025600c

Reference yield:

(1S,2R)-2-(methoxycarbonyl)cyclohex-4-ene-1-carboxylic acid (31139-02-3,31139-03-4,56124-48-2,88335-93-7,88335-94-8,93603-11-3) → (1S,2S)-Cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester (253454-00-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/S0957-4166(99)00345-6

Reference yield:

(1S,6S)-6-(2-oxooxazolidine-3-carbonyl)-cyclohex-3-enecarboxylic acid methyl ester (141435-12-3) → (1S,2S)-Cyclohex-4-ene-1,2-dicarboxylic acid monomethyl ester (253454-00-1)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 17h;

DOI:10.1016/j.tetasy.2003.07.022

upstream raw materials:

(1S,2R)-2-(methoxycarbonyl)cyclohex-4-ene-1-carboxylic acid

(1S,6S)-6-(2-oxooxazolidine-3-carbonyl)-cyclohex-3-enecarboxylic acid methyl ester

(1R,6R)-6-(2-oxo-oxazolidine-3-carbonyl)-cyclohex-3-ene carboxylic acid methyl ester

3-[(E)-3-(methoxycarbonyl)-propenoyl]-oxazolidin-2-one

Downstream raw materials:

(1R,6R)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester

(1S,2S)-2-methanesulfonylaminocyclohexanecarboxylic acid methyl ester

(1S,2S)-2-methanesulfonylaminocyclohexanecarboxylic acid

(1S,6S)-6-benzyloxycarbonylaminocyclohex-3-enecarboxylic acid methyl ester