methyl 1-methyl-cis-1,2-cyclohexanedicarboxylate | 1228048-51-8

• 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: methyl 1-methyl-cis-1,2-cyclohexanedicarboxylate
• 英文别名: (+/-)-1-methyl-cyclohexane-1r,2c-dicarboxylic acid-2-methyl ester；(+/-)-1-Methyl-cyclohexan-1r,2c-dicarbonsaeure-2-methylester；(1S,2R)-2-(methoxycarbonyl)-1-methylcyclohexanecarboxylic acid；(1S,2R)-2-methoxycarbonyl-1-methylcyclohexane-1-carboxylic acid
• CAS: 1228048-51-8
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: XYGHTDSWXSMJFG-XVKPBYJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-methyl-cis-1,2-cyclohexanedicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以95%的产率得到cis-1-methyl-1,2-bis(hydroxymethyl)cyclohexane
  参考文献：
  名称：

  Conformational equilibrium in 8-methyl-cis-2-thiahydrindane and 8-methyl-cis-2-oxahydrindane by13C NMR spectroscopy

  摘要：

  AbstractThe preferred conformation of 8‐methyl‐cis‐thiahydrindane has been both estimated by 13C NMR chemical shifts and determined by low temperature 13C NMR spectroscopy to be the conformer with the methyl group equatorial with respect to the cyclohexane ring. This result is in disagreement with the interpretation of the temperature dependence of the CD spectra of (+) and (−) 8‐methyl‐cis‐2‐thiahydrindane, whereby the conformation with the methyl group axial with respect to the cyclohexane ring was claimed to be the preferred conformation. The preferred conformation of the related oxygen heterocycle, 8‐methyl‐cis‐2‐oxahydrindane, has been estimated by 13C NMR chemical shifts to be the conformer with the methyl group axial with respect to the cyclohexane ring. Possible reasons for these observations are discussed.

  DOI：

  10.1002/mrc.1270160403
• 作为产物：
  描述：

  柠康酸酐 在 palladium on activated charcoal 氢气 、 对苯二酚 作用下， 以 甲苯 为溶剂， 120.0 ℃ 、413.69 kPa 条件下， 反应 5.0h， 生成 methyl 1-methyl-cis-1,2-cyclohexanedicarboxylate
  参考文献：
  名称：

  Conformational equilibrium in 8-methyl-cis-2-thiahydrindane and 8-methyl-cis-2-oxahydrindane by13C NMR spectroscopy

  摘要：

  AbstractThe preferred conformation of 8‐methyl‐cis‐thiahydrindane has been both estimated by 13C NMR chemical shifts and determined by low temperature 13C NMR spectroscopy to be the conformer with the methyl group equatorial with respect to the cyclohexane ring. This result is in disagreement with the interpretation of the temperature dependence of the CD spectra of (+) and (−) 8‐methyl‐cis‐2‐thiahydrindane, whereby the conformation with the methyl group axial with respect to the cyclohexane ring was claimed to be the preferred conformation. The preferred conformation of the related oxygen heterocycle, 8‐methyl‐cis‐2‐oxahydrindane, has been estimated by 13C NMR chemical shifts to be the conformer with the methyl group axial with respect to the cyclohexane ring. Possible reasons for these observations are discussed.

  DOI：

  10.1002/mrc.1270160403

文献信息

• Quinazolines. Part XVI. A stereospecific cis-addition of the elements of nitromethane across a tetrasubstituted ethylenic double bond
  作者：W. L. F. Armarego

  DOI：10.1039/j39710001812

  日期：——

  -2-methylcyclohexanecarboxylate. A Schmidt reaction gave the cis-2-amino-derivative, which was converted via the 1-carbohydrazide into cis-2-aminomethyl-1-methylcyclohexylamine, which was cyclised with phosgene. A Hofmann reaction with methyl cis-2-carbamoyl-trans-2-methylcyclohexanecarboxylate, however, gave cis-2-amino-1-methylcyclohexanecarboxylic acid, which was converted into 4a-methyl-cis-oc

  3,4,5,6,7,8-六氢喹唑啉-2（1 H）-one与硝基乙酸在大约1℃熔融。60°得到高产率的8a-硝基甲基-顺式-八氢喹唑啉-2（1H）-一。该产物的立体化学通过推导出1个H NMR光谱和通过转化，通过氨甲基和溴甲基衍生物，为图8a甲基-顺-octahydroquinazolin-2（1 ħ） -酮。后者的真实样品由顺式-2-氯羰基-反式-2-甲基环己烷甲酸甲酯制备。施密特反应产生顺式-2-氨基衍生物，可通过将1-碳酰肼转化为顺式-2-氨基甲基-1-甲基环己胺，并用光气环化。然而，与顺式-2-氨基甲酰基-反式-2-甲基环己烷羧酸甲酯的霍夫曼反应产生了顺式-2-氨基-1-甲基环己烷羧酸，将其转化为4a-甲基-顺式-八氢喹唑啉-2（1 H）- 。
• 114. Fused carbon rings. Part IX. The synthesis of stereoisomeric 1-methylcyclohexane-1 : 2-dicarboxylic acids and of various methylcyclohexanecarboxylicacetic acids. The influence of the angular methyl group on the stability of their anhydrides
  作者：R. P. Linstead、A. F. Millidge

  DOI：10.1039/jr9360000478

  日期：——
• Technological change and industrial relations
  作者：Daphne G. Taras、James T. Bennett

  DOI：10.1007/s12122-002-1039-x

  日期：2002.9
• Conformational equilibrium in 8-methyl-cis-2-thiahydrindane and 8-methyl-cis-2-oxahydrindane by13C NMR spectroscopy
  作者：Rodney L. Willer

  DOI：10.1002/mrc.1270160403

  日期：1981.8

  AbstractThe preferred conformation of 8‐methyl‐cis‐thiahydrindane has been both estimated by 13C NMR chemical shifts and determined by low temperature 13C NMR spectroscopy to be the conformer with the methyl group equatorial with respect to the cyclohexane ring. This result is in disagreement with the interpretation of the temperature dependence of the CD spectra of (+) and (−) 8‐methyl‐cis‐2‐thiahydrindane, whereby the conformation with the methyl group axial with respect to the cyclohexane ring was claimed to be the preferred conformation. The preferred conformation of the related oxygen heterocycle, 8‐methyl‐cis‐2‐oxahydrindane, has been estimated by 13C NMR chemical shifts to be the conformer with the methyl group axial with respect to the cyclohexane ring. Possible reasons for these observations are discussed.