methyl (3-chloro-2-hydroxy-3-phenyl)propionate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (3-chloro-2-hydroxy-3-phenyl)propionate
• 英文别名: Methyl 3-chloro-2-hydroxy-3-phenylpropanoate
• 化学式: C₁₀H₁₁ClO₃
• 分子量: 214.649
• InChiKey: OZWSWCDGHNEYLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯基环氧乙烷-1-羧酸甲酯 在 indium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到methyl (3-chloro-2-hydroxy-3-phenyl)propionate
  参考文献：
  名称：

  Indium(III) Chloride-Promoted Rearrangement of Epoxides: A Selective Synthesis of Substituted Benzylic Aldehydes and Ketones

  摘要：

  A simple and efficient procedure for the rearrangement of substituted epoxides catalyzed by InCl3 has been developed. Aryl-substituted epoxides isomerize with complete regioselectivity to form a single carbonyl compound via cleavage of the benzylic C-O bond. The reactions are simple, fast, and high yielding. This procedure is very mild compared to those catalyzed with BF3 and other Lewis acids and compatible with several acid-sensitive functionalities. This protocol provides a highly selective synthesis of substituted benzylic aldehydes and ketones. However, rearrangement of alkyl-substituted epoxides is not very selective.

  DOI：

  10.1021/jo980793w

文献信息

• Sosnovskii, G. M.; Astapovich, I. V., Russian Journal of Organic Chemistry, 1993, vol. 29, # 1.1, p. 71 - 73
  作者：Sosnovskii, G. M.、Astapovich, I. V.

  DOI：——

  日期：——
• [EN] SYNTHESIS AND OPTICAL RESOLUTION OF THE TAXOL SIDE CHAIN AND RELATED COMPOUNDS
  申请人：THE UNIVERSITY OF MISSISSIPPI

  公开号：WO1993010076A1

  公开（公告）日：1993-05-27

  (EN) This invention relates to a method for the production of a substantially optically pure taxane side chain comprising the steps of synthesizing a racemic mixture of enantiomers of the taxane side chain that is capable of exhibiting conglomerate behavior and resolving the substantially optically pure enantiomers by direct crystallization methods. This invention also relates to the semisynthesis of taxanes such as taxol through coupling the substantially optically pure taxane side chain to a taxane ring nucleus.(FR) Cette invention concerne un procédé de production d'une chaîne latérale de taxane sensiblement optiquement pure comprenant les étapes de synthèse d'un mélange racémique d'énantiomères de la chaîne latérale de taxane qui est capable de se comporter comme un conglomérat et de dissoudre les énantiomères sensiblement optiquement purs par des procédés de cristallisation directe. Cette invention concerne également la semi-synthèse de taxanes tels que le taxol par couplage de la chaîne latérale de taxane sensiblement pure à un noyau du cycle de taxane.
• Indium(III) Chloride-Promoted Rearrangement of Epoxides: A Selective Synthesis of Substituted Benzylic Aldehydes and Ketones
  作者：Brindaban C. Ranu、Umasish Jana

  DOI：10.1021/jo980793w

  日期：1998.11.1

  A simple and efficient procedure for the rearrangement of substituted epoxides catalyzed by InCl3 has been developed. Aryl-substituted epoxides isomerize with complete regioselectivity to form a single carbonyl compound via cleavage of the benzylic C-O bond. The reactions are simple, fast, and high yielding. This procedure is very mild compared to those catalyzed with BF3 and other Lewis acids and compatible with several acid-sensitive functionalities. This protocol provides a highly selective synthesis of substituted benzylic aldehydes and ketones. However, rearrangement of alkyl-substituted epoxides is not very selective.