(1S,2S,5R)-methane sulfonic acid-[(5-methyl-2-prop-2-yl)-cyclohexyl-1-yl]-ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2S,5R)-methane sulfonic acid-[(5-methyl-2-prop-2-yl)-cyclohexyl-1-yl]-ester
• 英文别名: (1S,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate；[(1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] methanesulfonate
• 化学式: C₁₁H₂₂O₃S
• 分子量: 234.36
• InChiKey: JHBDQWDYNMJVIB-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,5R)-methane sulfonic acid-[(5-methyl-2-prop-2-yl)-cyclohexyl-1-yl]-ester 、 苯甲酸 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以89%的产率得到(-)-薄荷基苯甲酸酯
  参考文献：
  名称：

  Inversion of secondary chiral alcohols in toluene with the tunable complex of R3NR′COOH

  摘要：

  The S(N)2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R'COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR'COOH is crucial for the S(N)2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.028
• 作为产物：
  描述：

  (1Alpha,2Alpha,5β)-(+-)-5-甲基 、 甲基磺酰氯 以 吡啶 为溶剂， 反应 15.0h， 以100%的产率得到(1S,2S,5R)-methane sulfonic acid-[(5-methyl-2-prop-2-yl)-cyclohexyl-1-yl]-ester
  参考文献：
  名称：

  Kagan的薄荷基取代的二茂钛和二茂锆锆的合成方法改进，晶体结构比较和初步催化剂评估

  摘要：

  描述了1和2的改进的合成，其允许以催化应用所需的多克量获得这些络合物。比较了1和2的晶体结构，并讨论了对催化应用很重要的配体的构象偏好。评价复合物2作为碳镁反应的催化剂。

  DOI：

  10.1016/j.jorganchem.2005.10.026

文献信息

• Practical Synthesis of Optically Pure Menthylamines Starting from Racemic Neomenthol
  作者：Siegfried Waldvogel、Nina Welschoff

  DOI：10.1055/s-0030-1258295

  日期：2010.11

  scalable route to racemic and highly enantiomerically enriched menthylamines exploits the technical product rac-neomenthol as the starting material. The elaborated protocol is based on nucleophilic substitution of the hydroxy moiety by azide. Subsequent reduction and resolution with tartaric acid provides the desired optically enriched menthylamines. amines - azides - chiral resolution - reduction - terpenoids

  可靠的，可扩展的途径生产外消旋和高度对映异构体富集的薄荷胺，采用了技术产品外消旋-薄荷脑作为原料。精心设计的方案基于叠氮化物对羟基部分的亲核取代。随后用酒石酸还原和拆分得到所需的光学富集的薄荷胺。 胺-叠氮化物-手性拆分-还原-萜类化合物
• An improved synthesis of Kagan’s menthyl substituted titanocene and zirconocene dichloride, comparison of their crystal structures, and preliminary catalyst evaluation
  作者：Andreas Gansäuer、Sanjay Narayan、Noëllie Schiffer-Ndene、Harald Bluhm、J. Enrique Oltra、Juan Manuel Cuerva、Antonio Rosales、Martin Nieger

  DOI：10.1016/j.jorganchem.2005.10.026

  日期：2006.5

  An improved synthesis of 1 and 2 is described that allows access to these complexes in multigram quantities necessary for catalytic applications. The crystal structures of 1 and 2 are compared and the conformational preferences of the ligands, that are important for catalytic applications, are discussed. Complex 2 was evaluated as a catalyst for carbomagnesation reactions.

  描述了1和2的改进的合成，其允许以催化应用所需的多克量获得这些络合物。比较了1和2的晶体结构，并讨论了对催化应用很重要的配体的构象偏好。评价复合物2作为碳镁反应的催化剂。
• Inversion of secondary chiral alcohols in toluene with the tunable complex of R3NR′COOH
  作者：Xiao-Xin Shi、Chun-Li Shen、Jian-Zhong Yao、Liang-Deng Nie、Na Quan

  DOI：10.1016/j.tetasy.2009.12.028

  日期：2010.3

  The S(N)2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R'COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR'COOH is crucial for the S(N)2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields. (C) 2010 Elsevier Ltd. All rights reserved.