(1S,2R,5S)-Menthyl (S)-mandelate | 25926-72-1

• 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,2R,5S)-Menthyl (S)-mandelate
• 英文别名: S-(+)-Mandelsaeure-(+)-menthylester；L-mandelic acid-((1S)-menthyl ester)；L-Mandelsaeure-((1S)-menthylester)；L-Mandelsaeure-((1S)-3c-methyl-6t-isopropyl-cyclohexyl-(r)-ester)；[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] (2S)-2-hydroxy-2-phenylacetate
• CAS: 25926-72-1
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: XEOQHVVLXIUVHB-ORQFMDKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  D-薄荷醇 在 rhodium(II) acetate dimer 水 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (1S,2R,5S)-Menthyl (S)-mandelate
  参考文献：
  名称：

  Diastereoselectivity in the O-H Insertion Reactions of Rhodium Carbenoids Derived from Phenyldiazoacetates of Chiral Alcohols. Preparation of .alpha.-Hydroxy and .alpha.-Alkoxy Esters

  摘要：

  A series of phenyldiazoacetates 3 derived from enantiomerically pure alcohols ((-)-borneol, (+)menthol, (-)-menthol, (-)-8-phenylmenthol, (-)-trans-2-phenylcyclohexanol, (+)-trans-2-phenyl-cyclohexanol, and (-)10-(dicyclohexylsulfamoyl)-D-isoborneol) were prepared from the corresponding alpha-keto esters 1 by way of the tosylhydrazones 2. Rhodium(II)-catalyzed decomposition of the diazoacetates 3 in the presence of water or alcohols resulted in carbenoid O-H insertion reactions to give the corresponding 2-hydroxy- or 2-alkoxyphenylacetates in good yield, but with varying degrees of diastereoselectivity. A range of rhodium(II) and other metal catalysts were investigated, with rhodium(II) acetate and rhodium(II) acetamide giving the best results. The stereochemistry of the major diastereomer was proved in most cases by independent synthesis from a mandelic acid derivative of known configuration. Possible mechanisms are discussed.

  DOI：

  10.1021/jo00119a023

文献信息

• Asymmetric intramolecular Cannizzaro reaction of anhydrous phenylglyoxal
  作者：Kazuaki Ishihara、Takayuki Yano、Makoto Fushimi

  DOI：10.1016/j.jfluchem.2008.04.008

  日期：2008.10

  The use of anhydrous phenylglyoxal provides a solution to the problem of low reactivity in the asymmetric intramolecular Cannizzaro reaction with alcohols. Double asymmetric induction was achieved in the reaction of anhydrous phenylglyoxal with D-(+)-menthol promoted by a (SS)-t-BuBox center dot copper(II) hexafluoroantimonate complex. (C) 2008 Elsevier B.V. All rights reserved.
• McKenzie; Luis, Chemische Berichte, 1936, vol. 69, p. 1118,1121
  作者：McKenzie、Luis

  DOI：——

  日期：——