(8S)-8-hydroxypentadecanoic acid 2-phenylethyl amide

• 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: (8S)-8-hydroxypentadecanoic acid 2-phenylethyl amide
• 英文别名: (8S)-8-hydroxy-N-(2-phenylethyl)pentadecanamide
• 化学式: C₂₃H₃₉NO₂
• 分子量: 361.568
• InChiKey: JJZSGRYZZBAVAB-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (5-羧基戊基)三苯基溴化磷 在 palladium on activated charcoal 4-二甲氨基吡啶 、 正丁基锂 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 (8S)-8-hydroxypentadecanoic acid 2-phenylethyl amide
  参考文献：
  名称：

  Asymmetric synthesis of a cytotoxic amide of Telesto riisei

  摘要：

  An efficient synthesis of both the enantiomers of N-(2-phenylethyl)-8-hydroxypentadecacarboxamide using the cytotoxic principles of Telesto riisei has been formulated using cyclohexylideneglyceraldehyde 1 as the chiral template. A non-stereoselective Grignard addition to the aldehyde 1 gave the C-3 epimers of the required chiron, 3-alkylglycerol which were converted to the title compound via a standard sequence of reactions. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00091-3

文献信息

• Asymmetric synthesis of a cytotoxic amide of Telesto riisei
  作者：Sivaraman Sankaranarayanan、Subrata Chattopadhyay

  DOI：10.1016/s0957-4166(98)00091-3

  日期：1998.4

  An efficient synthesis of both the enantiomers of N-(2-phenylethyl)-8-hydroxypentadecacarboxamide using the cytotoxic principles of Telesto riisei has been formulated using cyclohexylideneglyceraldehyde 1 as the chiral template. A non-stereoselective Grignard addition to the aldehyde 1 gave the C-3 epimers of the required chiron, 3-alkylglycerol which were converted to the title compound via a standard sequence of reactions. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.