(Z)-7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((E)-oct-1-enyl)-6-oxo-cyclohexyl]-hept-5-enoic acid methyl ester | 315221-01-3

• 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: (Z)-7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((E)-oct-1-enyl)-6-oxo-cyclohexyl]-hept-5-enoic acid methyl ester
• CAS: 315221-01-3
• 化学式: C₂₈H₅₀O₄Si
• 分子量: 478.788
• InChiKey: WAOJVWCIGBLDHI-PAYSFZSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.79
• 重原子数：
  33.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((E)-oct-1-enyl)-6-oxo-cyclohexyl]-hept-5-enoic acid methyl ester 在 吡啶 、 氢氟酸 作用下， 以 乙腈 为溶剂， 以79%的产率得到methyl (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E)-oct-1-enyl]-6-oxocyclohexyl]hept-5-enoate
  参考文献：
  名称：

  Solution- and Soluble-Polymer Supported Asymmetric Syntheses of Six-Membered Ring Prostanoids

  摘要：

  An asymmetric synthesis of prostanoids containing a six-membered ring core structure (11a-homoprostaglandins), both in solution and using non-cross-linked polystyrene (NCPS) as a soluble support, was developed. Target molecule 1 was generated in a convergent fashion using a three-component coupling strategy, wherein chiral enone (R)-2 was the precursor of the central ring and the cuprate 3 and triflate 4 were used to introduce the side chains. The chiral center of (R)-2 directed the facial selectivity of the conjugate addition reaction which then dictated the stereochemical outcome of the subsequent alpha alkylation. Attachment of a six-membered ring scaffold to NCPS facilitated purification without compromising synthetic yields, still allowed H-1-NMR analysis of the intermediates in the synthesis, and provided an avenue for the construction of six-membered ring prostanoid libraries.

  DOI：

  10.1002/1521-3765(20000602)6:11<1917::aid-chem1917>3.0.co;2-7
• 作为产物：
  描述：

  (3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-((E)-oct-1-enyl)-1-trimethylsilanyloxy-cyclohexene 在 5percent Pd/BaSO₄ 喹啉 、 甲基锂 、 氢气 作用下， 以 四氢呋喃 、 环己烷 、 苯 为溶剂， -30.0~40.0 ℃ 、101.33 kPa 条件下， 反应 4.83h， 生成 (Z)-7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((E)-oct-1-enyl)-6-oxo-cyclohexyl]-hept-5-enoic acid methyl ester
  参考文献：
  名称：

  Solution- and Soluble-Polymer Supported Asymmetric Syntheses of Six-Membered Ring Prostanoids

  摘要：

  An asymmetric synthesis of prostanoids containing a six-membered ring core structure (11a-homoprostaglandins), both in solution and using non-cross-linked polystyrene (NCPS) as a soluble support, was developed. Target molecule 1 was generated in a convergent fashion using a three-component coupling strategy, wherein chiral enone (R)-2 was the precursor of the central ring and the cuprate 3 and triflate 4 were used to introduce the side chains. The chiral center of (R)-2 directed the facial selectivity of the conjugate addition reaction which then dictated the stereochemical outcome of the subsequent alpha alkylation. Attachment of a six-membered ring scaffold to NCPS facilitated purification without compromising synthetic yields, still allowed H-1-NMR analysis of the intermediates in the synthesis, and provided an avenue for the construction of six-membered ring prostanoid libraries.

  DOI：

  10.1002/1521-3765(20000602)6:11<1917::aid-chem1917>3.0.co;2-7