methyl 5-trimethylsilyl-4-pentynoate | 180922-91-2

• 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: methyl 5-trimethylsilyl-4-pentynoate
• 英文别名: 4-Pentynoic acid, 5-(trimethylsilyl)-, methyl ester；methyl 5-trimethylsilylpent-4-ynoate
• CAS: 180922-91-2
• 化学式: C₉H₁₆O₂Si
• 分子量: 184.31
• InChiKey: DJLBZWDVQRNPBX-UHFFFAOYSA-N

物化性质

• 沸点：
  198.9±23.0 °C(Predicted)
• 密度：
  0.923±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 5-trimethylsilyl-4-pentynoate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.38h， 以85.4%的产率得到5-(trimethylsilyl)pent-4-ynal
  参考文献：
  名称：

  Synthesis of (E,Z)-5-Bromo-1,1-dimethoxy-5-trimethylsilyl-4-pentene, an Upper Chain Allenic Prostaglandin Building Block

  摘要：

  This work explores the synthetic route to allenic prostaglandins. In a search for more efficient and reliable methods for the introduction of the allene moiety into the side chains of prostaglandins, the synthons, the (E) and (Z) isomers of 1-bromo-5,5-dimethoxy-1-trimethylsilyl-1-pentene (13a) and (13b), have been prepared and converted to R,S-1,1-dimetboxy-6-phenyl-4,5-hexadiene (16), a prostaglandin analog.

  DOI：

  10.1081/scc-120023984
• 作为产物：
  描述：

  1-(3-butynyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 在 silica gel 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver(I) chloride 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 97.0h， 生成 methyl 5-trimethylsilyl-4-pentynoate
  参考文献：
  名称：

  Synthesis of (E,Z)-5-Bromo-1,1-dimethoxy-5-trimethylsilyl-4-pentene, an Upper Chain Allenic Prostaglandin Building Block

  摘要：

  This work explores the synthetic route to allenic prostaglandins. In a search for more efficient and reliable methods for the introduction of the allene moiety into the side chains of prostaglandins, the synthons, the (E) and (Z) isomers of 1-bromo-5,5-dimethoxy-1-trimethylsilyl-1-pentene (13a) and (13b), have been prepared and converted to R,S-1,1-dimetboxy-6-phenyl-4,5-hexadiene (16), a prostaglandin analog.

  DOI：

  10.1081/scc-120023984

文献信息

• Synthesis of (E,Z)-5-Bromo-1,1-dimethoxy-5-trimethylsilyl-4-pentene, an Upper Chain Allenic Prostaglandin Building Block
  作者：Guzman-Duran, Antonio、Guzman, Esther、Pannell, Keith H.、Lloyd, Winston D.

  DOI：10.1081/scc-120023984

  日期：2003.9

  This work explores the synthetic route to allenic prostaglandins. In a search for more efficient and reliable methods for the introduction of the allene moiety into the side chains of prostaglandins, the synthons, the (E) and (Z) isomers of 1-bromo-5,5-dimethoxy-1-trimethylsilyl-1-pentene (13a) and (13b), have been prepared and converted to R,S-1,1-dimetboxy-6-phenyl-4,5-hexadiene (16), a prostaglandin analog.