7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-oxo-2-((E)-3-phenyl-propenyl)-cyclohexyl]-hept-5-ynoic acid methyl ester | 315220-98-5

• 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: 7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-oxo-2-((E)-3-phenyl-propenyl)-cyclohexyl]-hept-5-ynoic acid methyl ester
• CAS: 315220-98-5
• 化学式: C₂₉H₄₂O₄Si
• 分子量: 482.736
• InChiKey: CNFIROLZQPWKOJ-FVIJCQLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-oxo-2-((E)-3-phenyl-propenyl)-cyclohexyl]-hept-5-ynoic acid methyl ester 在 5percent Pd/BaSO₄ 吡啶 、 喹啉 、 氢氟酸 、 氢气 作用下， 以 环己烷 、 乙腈 、 苯 为溶剂， 40.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 methyl (Z)-7-[(1R,2R,3R)-3-hydroxy-6-oxo-2-[(E)-3-phenylprop-1-enyl]cyclohexyl]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：

  (4R)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-en-1-one 在 甲基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 生成 7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-oxo-2-((E)-3-phenyl-propenyl)-cyclohexyl]-hept-5-ynoic 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