Acetic acid (1S,4S)-4-{4-[1-(tert-butyl-dimethyl-silanyloxy)-hexyl]-phenyl}-cyclopent-2-enyl ester | 836643-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: Acetic acid (1S,4S)-4-{4-[1-(tert-butyl-dimethyl-silanyloxy)-hexyl]-phenyl}-cyclopent-2-enyl ester
• CAS: 836643-55-1
• 化学式: C₂₅H₄₀O₃Si
• 分子量: 416.676
• InChiKey: CYWGWJDCVAKUPR-YOQGVNIDSA-N

物化性质

• 沸点：
  464.2±45.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,4S)-4-{4-[1-(tert-butyl-dimethyl-silanyloxy)-hexyl]-phenyl}-cyclopent-2-enyl ester 在 三乙基硼氢化锂 、 碳酸氢钠 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 29.0h， 生成 7-(5-(4-(1-(t-butyldimethylsilyloxy)hexyl)phenyl)-2-oxo-cyclopentyl)heptanal
  参考文献：
  名称：

  New Reagent System for Attaining High Regio- and Stereoselectivities in Allylic Displacement of 4-Cyclopentene-1,3-diol Monoacetate with Aryl- and Alkenylmagnesium Bromides

  摘要：

  Low regioselectivity of RMgBr (R = aryl, alkenyl) in the CuCN-catalyzed reaction with 4-cyclopentene-1.3-diol monoacetate is improved by addition of LiCl or MgCl2 to a similar extent as previously obtained with RMgCl (>90:10). The limitation encountered in the preparation of RMgCl no longer exists in the present method using RMgBr. The method is utilized in the synthesis of AH-13205. a selective EP2-receptor agonist.

  DOI：

  10.1021/ol047953c
• 作为产物：
  描述：

  正戊基溴化镁 在 吡啶 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 Acetic acid (1S,4S)-4-{4-[1-(tert-butyl-dimethyl-silanyloxy)-hexyl]-phenyl}-cyclopent-2-enyl ester
  参考文献：
  名称：

  New Reagent System for Attaining High Regio- and Stereoselectivities in Allylic Displacement of 4-Cyclopentene-1,3-diol Monoacetate with Aryl- and Alkenylmagnesium Bromides

  摘要：

  Low regioselectivity of RMgBr (R = aryl, alkenyl) in the CuCN-catalyzed reaction with 4-cyclopentene-1.3-diol monoacetate is improved by addition of LiCl or MgCl2 to a similar extent as previously obtained with RMgCl (>90:10). The limitation encountered in the preparation of RMgCl no longer exists in the present method using RMgBr. The method is utilized in the synthesis of AH-13205. a selective EP2-receptor agonist.

  DOI：

  10.1021/ol047953c