3205-35-4

Basic information

• Product Name: dimethyl cyclohexane-1,2-dicarboxylate
• Synonyms: Dimethyl trans-1,2-Cyclohexanedicarboxylate;trans-1,2-Cyclohexanedicarboxylic Acid Dimethyl Ester;trans-Cyclohexane-1,2-dicarboxylic acid dimethyl ester;trans-DiMethyl cyclohexane-1,2-dicarboxylate;Dimethyl trans-1,2-Cyclohexanedicarboxylate
• CAS NO: 3205-35-4
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.23
• Mol File: 3205-35-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 75 °C / 0.8mmHg
• Flash Point: 121.3°C
• Appearance: /
• Density: 1.10
• Vapor Pressure: 0.0133mmHg at 25°C
• Refractive Index: 1.4520-1.4560
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: dimethyl cyclohexane-1,2-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl cyclohexane-1,2-dicarboxylate(3205-35-4)
• EPA Substance Registry System: dimethyl cyclohexane-1,2-dicarboxylate(3205-35-4)

Safety Data

• Hazardous Substances Data: 3205-35-4(Hazardous Substances Data)

Usage

Uses

Dimethyl trans-1,2-Cyclohexanedicarboxylate is used in an improved process for prepnaration of Lurasidone Hydrochloride starting from Cyclohexanedicarboxylic Acid.

InChI:InChI=1/C10H16O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h7-8H,3-6H2,1-2H3/t7-,8-/m0/s1

Upstream product

• 131-11-3 phthalic acid dimethyl ester 
• 868-74-6 2,7-dibromooctanedioic acid dimethyl ester 
• 110-52-1 1,4-dibromo-butane 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 67-56-1 methanol 
• 2305-32-0 trans-1,2-cyclohexanedicarboxylic acid 
• 74-88-4 methyl iodide 
• 624-49-7 dimethylfumarate 
• 186581-53-3 diazomethane 

Downstream Products

• 76155-27-6 (+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol 
• 17351-16-5 trans-1,2-bis(hydroxydiphenylmethyl)cyclohexane 
• 65376-05-8 (+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane 
• 10479-74-0 (+/-)-(trans-2-chloromethyl-cyclohexyl)-methanol 
• 186204-35-3 (1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate 
• 66347-68-0 (±)-(1S, 2S)-cyclohexane-1,2-dimethanol bis(methanesulfonate) 

Relevant articles and documents

Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds

Reversible cleavage of C(sp3)-H bonds can enable racemization or epimerization, offering a valuable tool to edit the stereochemistry of organic compounds. While epimerization reactions operating via cleavage of acidic C(sp3)-H bonds, such as the Cα-H of carbonyl compounds, have been widely used in organic synthesis and enzyme-catalyzed biosynthesis, epimerization of tertiary carbons bearing a nonacidic C(sp3)-H bond is much more challenging with few practical methods available. Herein, we report the first synthetically useful protocol for the epimerization of tertiary carbons via reversible radical cleavage of unactivated C(sp3)-H bonds with hypervalent iodine reagent benziodoxole azide and H2O under mild conditions. These reactions exhibit excellent reactivity and selectivity for unactivated 3° C-H bonds of various cycloalkanes and offer a powerful strategy for editing the stereochemical configurations of carbon scaffolds intractable to conventional methods. Mechanistic study suggests that the unique ability of N3? to serve as a catalytic H atom shuttle is critical to reversibly break and reform 3° C-H bonds with high efficiency and selectivity.

Synthesis of Dimethyl 1,2-Cycloalkanedicarboxylates by Electrochemical Cyclization of Dimethyl α,α-Dibromoalkanedioates Using a Copper Anode

The electrochemical cyclization of dimethyl α,α'-dibromoalkanedioates by making use of a platinum cathode and a copper anode in the presence of sodium iodide gave three- to six-membered dimethyl 1,2-cycloalkanedicarboxylates in good yields.

Regioselectivity in cycloaddition reactions on solid phases

A 1percent crosslinked divinylbenzene-styrene copolymer, incorporating benzyl acrylate groups, reacted in normal Diels-Alder reactions with E-1-phenyl-1,3-butadiene or methyl E-2,4-pentadienoate to give their respective polymer-bound benzyl cyclohexenecarboxylates.Polymer-bound benzyl propiolate and polymer-bound benzyl phenylpropiolate reacted with benzonitrile oxide in a typical 1,3-dipolar addition reaction to give their respective polymer-bound isoxazoles.Cleavage of the polymer-bound Diels-Alder adducts and the polymer-bound 1,3-dipolar addition adduct derived from polymer-bound benzyl propiolate gave mixtures of ortho and meta regiomers similar to those produced in analogous reactions in solution.Cleavage of the polymer-bound 1,3-dipolar addition adduct, derived from polymer-bound benzyl phenylpropiolate, followed by esterification, gave a solitary adduct, 4-carbomethoxy-3,5-diphenylisoxazole, but an analogous solution 1,3-dipolar addition yielded a 1:1 ratio of the two possible regiomers.