CIS-1,4-DIMETHYL CYCLOHEXANEDICARBOXYLATE

Base Information

• Chemical Name: CIS-1,4-DIMETHYL CYCLOHEXANEDICARBOXYLATE
• CAS No.: 3399-21-1
• Molecular Formula: C10H16O4
• Molecular Weight: 200.235
• Mol file: 3399-21-1.mol

Synonyms:CIS-1,4-DIMETHYL CYCLOHEXANEDICARBOXYLATE;1,4-Cyclohexanedicarboxylic acid, dimethyl ester, cis-;cis-Cyclohexan-dicarbonsaeure-(1.4)-dimethylester;cis-cyclohexane-1,4-dicarboxylic acid dimethyl ester;dimethyl cis-cyclohexane-1,4-dicarboxylate;cis-Cyclohexan-1,4-dicarbonsaeure-dimethylester;cis-Dimethyl cyclohexane-1,4-dicarboxylate;dimethyl 1,4-cyclohexanedicarboxylate;cis-1,4-Cyclohexandicarbonsaeure-dimethylester;dimethyl cyclohexane-cis-1,4-dicarboxylate;

Chemical Property of CIS-1,4-DIMETHYL CYCLOHEXANEDICARBOXYLATE

Chemical Property:

• Melting Point: 14°C
• Refractive Index: 1.4568 (estimate)
• Boiling Point: 297.96°C (rough estimate)
• PSA: 52.60000
• Density: 1.1112
• LogP: 1.13880
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%min ^*data from raw suppliers

cis-DimethylCyclohexane-1,4-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CIS-1,4-DIMETHYL CYCLOHEXANEDICARBOXYLATE

There total 16 articles about CIS-1,4-DIMETHYL CYCLOHEXANEDICARBOXYLATE 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:

7-Oxobicyclo<2.2.1>heptan-1-carbonylchlorid (79368-45-9) + trimethyl orthoformate (149-73-5) → methyl cyclohex-1-ene-1-carboxylate (18448-47-0) + methyl cyclohex-3-ene-1-carboxylate (6493-77-2) + dimethyl 1,4-cyclohexanedicarboxylate (3399-22-2) + cis-dimethyl 1,4-cyclohexanedicarboxylate (3399-21-1) + 7,7-Dimethoxybicyclo<2.2.1>heptan-1-carbonsaeure-methylester (79368-46-0)

Guidance literature:

Product distribution; multistep reaction; cata. decarbonylation with chlorocarbonylbis(triphenylphosphan)rhodium;

Reference yield:

dimethyl 1,4-cyclohexane dicarboxylate (94-60-0) → dimethyl 1,4-cyclohexanedicarboxylate (3399-22-2) + cis-dimethyl 1,4-cyclohexanedicarboxylate (3399-21-1)

Guidance literature:

With pyridine; In methanol; at 40 ℃; for 2h;

Reference yield:

diphenylzinc (1078-58-6) → cis-dimethyl 1,4-cyclohexanedicarboxylate (3399-21-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Ni(cod)2; DBU / tetrahydrofuran / 6 h / 0 °C / 760.05 Torr

1.2: tetrahydrofuran / 2 h / 0 °C

2.1: 42 mg / diethyl ether / 0 °C

3.1: H₂ / Pd/C / ethyl acetate / 20 °C

4.1: NaIO₄; RuCl₃ / acetonitrile; H₂O / 20 °C

4.2: diethyl ether / 0 °C

With ruthenium trichloride; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sodium periodate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; water; ethyl acetate; acetonitrile;

DOI:10.1021/ja004004f

upstream raw materials:

diazomethane

cis-cyclohexane-1,4-dicarboxylic acid

methanol

7-Oxobicyclo<2.2.1>heptan-1-carbonylchlorid

Downstream raw materials:

(1S,4S)-4-(methoxycarbonyl)cyclohexane-1-carboxylic acid

trans-Bis-1,4-(1'-methyl-1'-hydroxy-ethyl)-cyclohexan

3,5-dinitro-benzoic acid-(4-methylene-cyclohexylmethyl ester)

(1,4-cis-cyclohexanediyl)bis(methylene)dimethanesultonate

Refernces

• 1、 Tortajada, Andreu,Ninokata, Ryo,Martin, Ruben. "Ni-Catalyzed Site-Selective Dicarboxylation of 1,3-Dienes with CO2". supporting information. p. 2050 - 2053. Retrieved 2018/02/19.
• 2、 Kawai, Makoto,Sakurada, Isao,Morita, Asato,Iwamuro, Yuko,Ando, Kazuo,Omura, Hirofumi,Sakakibara, Sachiko,Masuda, Tsutomu,Koike, Hiroki,Honma, Teruki,Hattori, Kazunari,Takashima, Tadayuki,Mizuno, Kunihiko,Mizutani, Mayumi,Kawamura, Mitsuhiro. "Structure-activity relationship study of novel NR2B-selective antagonists with arylamides to avoid reactive metabolites formation". . p. 5537 - 5542. Retrieved 2008/03/14.