DL-mandelic acid-((1SR)-menthyl ester) | 25926-69-6

• 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: DL-mandelic acid-((1SR)-menthyl ester)
• 英文别名: DL-Mandelsaeure-[(1SR)-3c-methyl-6t-isopropyl-cyclohexyl-(r)-ester；DL-Mandelsaeure-((1SR)-menthylester)；[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] (2R)-2-hydroxy-2-phenylacetate
• CAS: 25926-69-6；25926-70-9；25926-71-0；25926-72-1；74185-85-6
• 化学式: C₁₈H₂₆O₃
• 分子量: 290.403
• InChiKey: XEOQHVVLXIUVHB-PQEBFOHHSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  399.8±22.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯化亚砜 、 DL-mandelic acid-((1SR)-menthyl ester) 生成 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  McKenzie; Smith, Journal of the Chemical Society, 1923, vol. 123, p. 1968,1975, 1977

  摘要：

  DOI：
• 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 DL-mandelic acid-((1SR)-menthyl ester)
  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

• 一种利用手性衍生试剂对DL-薄荷醇进行柱 前衍生高效液相色谱手性拆分的方法
  申请人：上海应用技术学院

  公开号：CN104529710B

  公开（公告）日：2017-05-03

  本发明公开一种利用手性衍生试剂对DL‑薄荷醇进行柱前衍生高效液相色谱手性拆分的方法，即使用手性芳香酸与DL‑薄荷醇进行柱前衍生化反应得具有紫外吸收的DL‑薄荷醇酯衍生物；再通过配有紫外可见光检测器的高效液相色谱仪，使用普通的非手性硅胶色谱柱，采用水相与有机相作为反相洗脱流动相，将上述所得DL‑薄荷醇酯衍生物配成浓度为0.5‑1.0 mg/mL的样品溶液，控制流速为0.4‑1.2 mL/min，进样量为2‑10µL，检测波长为210‑285 nm,色谱柱柱温箱为20‑35℃进行色谱柱分离，从而将上述所得的DL‑薄荷醇酯非对映异构体进行分离检测，最后再分别进行水解即得D‑薄荷醇和L‑薄荷醇。
• 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.
• 154. The resolution of dl-menthyl (–)mandelate
  作者：Alex. McKenzie、E. Margaret Luis

  DOI：10.1039/jr9340000715

  日期：——
• Diastereoselectivity in the O-H Insertion Reactions of Rhodium Carbenoids Derived from Phenyldiazoacetates of Chiral Alcohols. Preparation of .alpha.-Hydroxy and .alpha.-Alkoxy Esters
  作者：Enrique Aller、David S. Brown、Geoffrey G. Cox、David J. Miller、Christopher J. Moody

  DOI：10.1021/jo00119a023

  日期：1995.7

  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.
• McKenzie; Smith, Journal of the Chemical Society, 1923, vol. 123, p. 1968,1975, 1977
  作者：McKenzie、Smith

  DOI：——

  日期：——