(3S,5R)-2-Hexyl-3,5-dihydroxy-hexadecanoic acid methyl ester | 717129-75-4

• 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: (3S,5R)-2-Hexyl-3,5-dihydroxy-hexadecanoic acid methyl ester
• 英文别名: methyl (3S,5R)-2-hexyl-3,5-dihydroxyhexadecanoate
• CAS: 717129-75-4
• 化学式: C₂₃H₄₆O₄
• 分子量: 386.616
• InChiKey: BBCVQYRCEURKLR-QFMSAKRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  27
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5R)-2-Hexyl-3,5-dihydroxy-hexadecanoic acid methyl ester 在 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 3-己基四氢-4-羟基-6-十一烷基-2H-吡喃-2-酮
  参考文献：
  名称：

  Highly enantioselective hydrogenation of 3,5-diketo esters: a formal synthesis of tetrahydrolipstatin

  摘要：

  Compound 4, obtained via a sequence of two consecutive alkylations of methyl 3,5-dioxohexanoate (5), was transformed into the enantiomerically pure lactone (3S,4S,6R)-2 being the precursor of tetrahydrolipstatin (1). The reaction sequence involves asymmetric catalytic hydrogenation of 4 as a crucial step. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.128
• 作为产物：
  描述：

  3,5-二酮己酸甲酯 在 <(S)-BINAP>chloro(p-cymene)ruthenium chloride 正丁基锂 、 氢气 、 copper diacetate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 60.0 ℃ 、10.13 MPa 条件下， 反应 18.0h， 生成 (3S,5R)-2-Hexyl-3,5-dihydroxy-hexadecanoic acid methyl ester
  参考文献：
  名称：

  Highly enantioselective hydrogenation of 3,5-diketo esters: a formal synthesis of tetrahydrolipstatin

  摘要：

  Compound 4, obtained via a sequence of two consecutive alkylations of methyl 3,5-dioxohexanoate (5), was transformed into the enantiomerically pure lactone (3S,4S,6R)-2 being the precursor of tetrahydrolipstatin (1). The reaction sequence involves asymmetric catalytic hydrogenation of 4 as a crucial step. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.03.128

文献信息

• Highly enantioselective hydrogenation of 3,5-diketo esters: a formal synthesis of tetrahydrolipstatin
  作者：Jolanta Polkowska、Ewa Łukaszewicz、Jarosław Kiegiel、Janusz Jurczak

  DOI：10.1016/j.tetlet.2004.03.128

  日期：2004.5

  Compound 4, obtained via a sequence of two consecutive alkylations of methyl 3,5-dioxohexanoate (5), was transformed into the enantiomerically pure lactone (3S,4S,6R)-2 being the precursor of tetrahydrolipstatin (1). The reaction sequence involves asymmetric catalytic hydrogenation of 4 as a crucial step. (C) 2004 Elsevier Ltd. All rights reserved.