dimethyl ester of cis-1,3-dimethylcyclohexane-1,3-dicarboxylic acid | 1142-41-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl ester of cis-1,3-dimethylcyclohexane-1,3-dicarboxylic acid
• 英文别名: dimethyl (1S,3R)-1,3-dimethylcyclohexane-1,3-dicarboxylate
• CAS: 1142-41-2
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: GCPMLRIQKFPPNS-TXEJJXNPSA-N

物化性质

• 熔点：
  57 °C
• 沸点：
  90-93 °C(Press: 0.6 Torr)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl ester of cis-1,3-dimethylcyclohexane-1,3-dicarboxylic acid 生成 1,3-Dimethylcyclohexan-1,3-dicarbonsaeure
  参考文献：
  名称：

  Fluorescence sensing due to allosteric switching of pyrene functionalized cis-cyclohexane-1,3-dicarboxylate

  摘要：

  用二价和一价金属阳离子以及强酸和弱酸滴定芘官能化顺式环己烷-1,3-二甲酸酯时，其准分子/单体荧光比会降低。

  DOI：

  10.1039/a705445i
• 作为产物：
  描述：

  Cyano-[3-cyano-3-methyl-cyclohex-(E)-ylidene]-acetic acid ethyl ester 在 盐酸 、 氢氧化钾 作用下， 生成 dimethyl ester of cis-1,3-dimethylcyclohexane-1,3-dicarboxylic acid
  参考文献：
  名称：

  497.萜类化合物的综合研究。第十部分。（±）-clovan-9-one和（±）-clovane的立体定向合成

  摘要：

  DOI：

  10.1039/jr9650002749

文献信息

• Chemistry and Stereochemistry of Benzyl-Benzyl Interactions in MH+ Ions of Dibenzyl Esters upon Chemical Ionization and Collision-induced Dissociation Conditions
  作者：M. Edelson-Averbukh、A. Mandelbaum

  DOI：10.1002/(sici)1096-9888(199705)32:5<515::aid-jms504>3.0.co;2-b

  日期：1997.5

  Isobutane chemical ionization mass spectra of dibenzyl esters of a wide variety of aliphatic, olefinic, alicyclic and aromatic dicarboxylic acids exhibit abundant m/z 181 C14H13+ ions, indicating a highly general rearrangement process involving the formation of a new bond between the two benzyl groups. An extensive collision-induced dissociation and deuterium labeling study suggested that these ions are an almost equimolar mixture of isomeric alpha-o-tolylbenzyl, alpha-p-tolylbenzyl and p-benzylbenzyl cation structures, and this composition is identical for all the diesters examined This structural assignment of the C14H13+ ions suggests a mechanistic pathway for their generation, based on the formation of the new bond between tbe benzyl methylene group of the protonated benzoxycarbonyl and the phenyl ring of the otter ester moiety via pi- (and/or ion-neutral) and a-complexes. Stereoisomeric diesters show an unusual steric effect: trans-isomers give rise to much more abundant C14H13+ ions than the cis counterparts, This behavior is explained by stabilized proton-bridged structures of the MH+ ions of the cis-isomers. (C) 1997 by John Wiley & Sons, Ltd.
• Remote enzyme-coupled amine release
  作者：F. M. Menger、M. Ladika

  DOI：10.1021/jo00297a010

  日期：1990.5
• Mechanism of stereospecific alcohol elimination from cyclohexanetrans-1,3-dicarboxylates under electron impact ionization
  作者：A. Etinger、A. Idina、A. Mandelbaum

  DOI：10.1002/oms.1210290703

  日期：1994.7

  AbstractDiesters of cyclohexane trans‐1,3‐dicarboxylic acid give rise to major [M  ROH]+·. ions under electron impact ionization. A mass spectral study of the isomeric mixed methyl ethyl esters of the diacid, substituted by a methyl group at position 1 and deuterium labelled at position 3, indicates a stepwise mechanism for this alcohol elimination; the 3‐hydrogen (or deuterium) is transferred to the carbonyl of the 1‐ester group in the initial step. Subsequent migration of that hydrogen (or deuterium) to the alkoxyl of position 3 results in the highly site‐ and stereospecific alcohol elimination. CID spectra of the [M  ROH]+. ions obtained from the stereoisomeric diesters clearly show that they have different structures (or are different mixtures of structures).
• 497. Synthetical studies on terpenoids. Part X. Stereospecific syntheses of (±)-clovan-9-one and (±)-clovane
  作者：Anil Kumar Kundu、Nitya Gopal Kundu、Phanindra Chandra Dutta

  DOI：10.1039/jr9650002749

  日期：——
• Fluorescence sensing due to allosteric switching of pyrene functionalized cis-cyclohexane-1,3-dicarboxylate
  作者：Carol Monahan

  DOI：10.1039/a705445i

  日期：——

  The excimer/monomer fluorescence ratio for a pyrene functionalized cis-cyclohexane-1,3-dicarboxylate decreases upon titration with divalent and monovalent metal cations, as well as strong and weak acids.

  用二价和一价金属阳离子以及强酸和弱酸滴定芘官能化顺式环己烷-1,3-二甲酸酯时，其准分子/单体荧光比会降低。