13(S)-hydroxy-11(E)-octadecen-9-ynoic acid | 261359-08-4

• 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: 13(S)-hydroxy-11(E)-octadecen-9-ynoic acid
• 英文别名: (E,13S)-13-hydroxyoctadec-11-en-9-ynoic Acid
• CAS: 261359-08-4
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: FYPCNVCBWHQKJO-VMEIHUARSA-N

物化性质

• 沸点：
  468.4±35.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  13(S)-hydroxy-11(E)-octadecen-9-ynoic acid 在 锌 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 24.0h， 生成 13(s)-羟基-9z,11e-十八二烯酸
  参考文献：
  名称：

  Novel Synthetic Approach to (S)-Coriolic Acid

  摘要：

  A new synthetic approach to (S)-coriolic acid 1 has been developed, starting from the readily available (E)-1-bromo-2-trimethylsilylethene 4 and trimethylsilylacetylene 5. A simple acylation reaction of 4, followed by a coupling reaction of the halogenoderivative intermediate with 5 in the presence of a Pd(0) catalyst affords the monosilylated ketoenyne 7. After desilylation of 7, enantioselective reduction of the carbonyl group with (S)-BINAL-H leads to the alcohol 2 (e.c.=94%). A subsequent coupling reaction and stereoselective reduction of the triple bond affords the target molecule 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01003-0
• 作为产物：
  描述：

  1-trimethylsilyl-3(E)-decen-1-yn-5-one 在 六甲基磷酰三胺 、 potassium fluoride 、 lithium aluminium tetrahydride 、 正丁基锂 、 乙醇 、 (S)-binaphthol 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 2.0h， 生成 13(S)-hydroxy-11(E)-octadecen-9-ynoic acid
  参考文献：
  名称：

  Novel Synthetic Approach to (S)-Coriolic Acid

  摘要：

  A new synthetic approach to (S)-coriolic acid 1 has been developed, starting from the readily available (E)-1-bromo-2-trimethylsilylethene 4 and trimethylsilylacetylene 5. A simple acylation reaction of 4, followed by a coupling reaction of the halogenoderivative intermediate with 5 in the presence of a Pd(0) catalyst affords the monosilylated ketoenyne 7. After desilylation of 7, enantioselective reduction of the carbonyl group with (S)-BINAL-H leads to the alcohol 2 (e.c.=94%). A subsequent coupling reaction and stereoselective reduction of the triple bond affords the target molecule 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01003-0

文献信息

• Method of treating dry eye disorders using 13(S)-HODE and its analogs
  申请人：Klimko G. Peter

  公开号：US20060128803A1

  公开（公告）日：2006-06-15

  The topical use of 13(S)-HODE and analogs are disclosed for the treatment of dry eye disorders.

  本发明揭示了用于治疗干眼症的13(S)-HODE和类似物的局部应用。
• Novel Synthetic Approach to (S)-Coriolic Acid
  作者：Francesco Babudri、Vito Fiandanese、Giuseppe Marchese、Angela Punzi

  DOI：10.1016/s0040-4020(99)01003-0

  日期：2000.1

  A new synthetic approach to (S)-coriolic acid 1 has been developed, starting from the readily available (E)-1-bromo-2-trimethylsilylethene 4 and trimethylsilylacetylene 5. A simple acylation reaction of 4, followed by a coupling reaction of the halogenoderivative intermediate with 5 in the presence of a Pd(0) catalyst affords the monosilylated ketoenyne 7. After desilylation of 7, enantioselective reduction of the carbonyl group with (S)-BINAL-H leads to the alcohol 2 (e.c.=94%). A subsequent coupling reaction and stereoselective reduction of the triple bond affords the target molecule 1. (C) 1999 Elsevier Science Ltd. All rights reserved.