7-[(1R,2S,5R)-2-羟基-5-[(E,3S)-3-羟基辛-1-烯基]环戊基]庚酸 | 37785-98-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 7-[(1R,2S,5R)-2-羟基-5-[(E,3S)-3-羟基辛-1-烯基]环戊基]庚酸
• 英文名称: 11-Deoxy-PGF(1α)
• 英文别名: 11-Deoxyprostaglandin F1alpha；7-[(1R,2S,5R)-2-hydroxy-5-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]heptanoic acid
• CAS: 37785-98-1
• 化学式: C₂₀H₃₆O₄
• 分子量: 340.503
• InChiKey: HYBPXYQCXNOTFK-DUSCRHDRSA-N

物化性质

• 溶解度：
  DMF：>50 mg/ml（来自 PGF1a）； DMSO：>50 mg/ml（来自 PGF1a）；乙醇：>75 mg/ml（来自 PGF1a）； PBS pH 7.2：>2 mg/ml（来自 PGF1a）

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  11-Deoxy-PGF(1α)-methylester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 17.0h， 以90%的产率得到7-[(1R,2S,5R)-2-羟基-5-[(E,3S)-3-羟基辛-1-烯基]环戊基]庚酸
  参考文献：
  名称：

  A Catalytic Asymmetric Synthesis of 11-Deoxy-PGF_1α Using ALB, a Heterobimetallic Multifunctional Asymmetric Complex

  摘要：

  A catalytic asymmetric synthesis of 11-deoxy-PGF(1 alpha) has been achieved using a cascade Michael-aldol reaction as a key step. This cascade reaction was efficiently promoted by a catalytic use of AlLibis[(S)-binaphthoxide] complex (ALB) to give the three-component coupling product at room temperature in 92% ee and in 84% yield. The three-component coupling product was then converted to (+)-11-deoxy-PGF(1 alpha) through several steps, including an oxidative decarboxylation, an aldol reaction, and a Wharton reaction. Moreover, the racemic enone, 20 was transformed into 21, the three-component coupling product, a potential intermediate for PGF(1 alpha), in 97% ee and in 75% yield through catalytic kinetic resolution.

  DOI：

  10.1021/jo9723319

文献信息

• AMINO ACID SALTS OF PROSTAGLANDINS
  申请人：DeLong Mitchell A.

  公开号：US20100105775A1

  公开（公告）日：2010-04-29

  The present invention is directed to novel amino acid prostaglandin salts and methods of making and using them.

  本发明涉及新型氨基酸前列腺素盐及其制备和使用方法。
• US8470882B2
  申请人：——

  公开号：US8470882B2

  公开（公告）日：2013-06-25
• US8623918B2
  申请人：——

  公开号：US8623918B2

  公开（公告）日：2014-01-07
• US8722739B2
  申请人：——

  公开号：US8722739B2

  公开（公告）日：2014-05-13
• A Catalytic Asymmetric Synthesis of 11-Deoxy-PGF_1α Using ALB, a Heterobimetallic Multifunctional Asymmetric Complex
  作者：Ken-ichi Yamada、Takayoshi Arai、Hiroaki Sasai、Masakatsu Shibasaki

  DOI：10.1021/jo9723319

  日期：1998.5.1

  A catalytic asymmetric synthesis of 11-deoxy-PGF(1 alpha) has been achieved using a cascade Michael-aldol reaction as a key step. This cascade reaction was efficiently promoted by a catalytic use of AlLibis[(S)-binaphthoxide] complex (ALB) to give the three-component coupling product at room temperature in 92% ee and in 84% yield. The three-component coupling product was then converted to (+)-11-deoxy-PGF(1 alpha) through several steps, including an oxidative decarboxylation, an aldol reaction, and a Wharton reaction. Moreover, the racemic enone, 20 was transformed into 21, the three-component coupling product, a potential intermediate for PGF(1 alpha), in 97% ee and in 75% yield through catalytic kinetic resolution.