methyl 1-(4-pentenyl)-2-[1-(1-pyrrolidinylcarbonyl)-ethyl]-cyclopentane-carboxylate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 1-(4-pentenyl)-2-[1-(1-pyrrolidinylcarbonyl)-ethyl]-cyclopentane-carboxylate
• 英文别名: methyl (1S,2S)-2-[(2S)-1-oxo-1-pyrrolidin-1-ylpropan-2-yl]-1-pent-4-enylcyclopentane-1-carboxylate
• 化学式: C₁₉H₃₁NO₃
• 分子量: 321.46
• InChiKey: COCXYEXBAPMIBW-BXWFABGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-(4-pentenyl)-2-[1-(1-pyrrolidinylcarbonyl)-ethyl]-cyclopentane-carboxylate 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到1-hydroxymethyl-1-(4-pentenyl)-2-[1-(1-pyrrolidinylcarbonyl)-ethyl]-cyclopentane
  参考文献：
  名称：

  Further Studies of the Daphniphyllum Alkaloid Polycyclization Cascade

  摘要：

  The scope of the 2-azadiene intramolecular Diels-Alder cyclization, previously employed for synthesis of the Daphniphyllum alkaloids, has been further investigated. Through a series of 1,5-diol cyclization precursors the substitution pattern of both the dienophile and the 8-azadiene were examined. From these studies it was shown that the cascade reaction is tolerant toward a variety of alkyl-substituted dienophiles. However, it was also demonstrated that this reaction is very sensitive to the substitution pattern of the 2-azadiene. Alterations made to the structure of the 2-azadiene cause either competing side reactions or complete failure of the reaction cascade.

  DOI：

  10.1021/jo001145r
• 作为产物：
  描述：

  1-pyrrolidin-1-yl-propan-1-one 、 5-碘-1-戊烯 、 环戊烯-1-羧酸甲酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以71%的产率得到methyl 1-(4-pentenyl)-2-[1-(1-pyrrolidinylcarbonyl)-ethyl]-cyclopentane-carboxylate
  参考文献：
  名称：

  Further Studies of the Daphniphyllum Alkaloid Polycyclization Cascade

  摘要：

  The scope of the 2-azadiene intramolecular Diels-Alder cyclization, previously employed for synthesis of the Daphniphyllum alkaloids, has been further investigated. Through a series of 1,5-diol cyclization precursors the substitution pattern of both the dienophile and the 8-azadiene were examined. From these studies it was shown that the cascade reaction is tolerant toward a variety of alkyl-substituted dienophiles. However, it was also demonstrated that this reaction is very sensitive to the substitution pattern of the 2-azadiene. Alterations made to the structure of the 2-azadiene cause either competing side reactions or complete failure of the reaction cascade.

  DOI：

  10.1021/jo001145r

文献信息

• Further Studies of the <i>Daphniphyllum</i> Alkaloid Polycyclization Cascade
  作者：Grier A. Wallace、Clayton H. Heathcock

  DOI：10.1021/jo001145r

  日期：2001.1.1

  The scope of the 2-azadiene intramolecular Diels-Alder cyclization, previously employed for synthesis of the Daphniphyllum alkaloids, has been further investigated. Through a series of 1,5-diol cyclization precursors the substitution pattern of both the dienophile and the 8-azadiene were examined. From these studies it was shown that the cascade reaction is tolerant toward a variety of alkyl-substituted dienophiles. However, it was also demonstrated that this reaction is very sensitive to the substitution pattern of the 2-azadiene. Alterations made to the structure of the 2-azadiene cause either competing side reactions or complete failure of the reaction cascade.