methyl N-(3-butenyl)pipecolinate | 132910-65-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl N-(3-butenyl)pipecolinate
• 英文别名: Methyl 1-but-3-enylpiperidine-2-carboxylate
• CAS: 132910-65-7
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: GTFRSFCENDGTNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-(3-butenyl)pipecolinate 在 sodium hydroxide 、 NH₂O*HCl 、 二异丁基氢化铝 作用下， 以 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 0.75h， 生成 N-(3-butenyl)-2-piperidinecarboxaldehyde oxime
  参考文献：
  名称：

  Cycloadditions. 46. Thermally induced intramolecular oxime olefin cycloadditions leading to N-bridgehead systems. Stereochemistry and molecular mechanics calculations

  摘要：

  The intramolecular oxime olefin cycloaddition (IOOC) of proline and pipecolinic acid derivatives proceeds thermally with a high degree of stereoselectivity to provide a new route to functionalized pyrrolizidines, indolizidines, or quinolizidines. The ring closure proceeds with simultaneous stereoselective introduction of three or four stereocenters. Molecular mechanics calculations have been refined to accurately predict not only which stereoisomer is preferred but also the syn and anti coupling constants in these tricyclic molecules.

  DOI：

  10.1021/jo00008a038
• 作为产物：
  描述：

  六氢吡啶-alpha-羧酸 在 氯化亚砜 、 三乙胺 作用下， 以 苯 为溶剂， 反应 35.0h， 生成 methyl N-(3-butenyl)pipecolinate
  参考文献：
  名称：

  Cycloadditions. 46. Thermally induced intramolecular oxime olefin cycloadditions leading to N-bridgehead systems. Stereochemistry and molecular mechanics calculations

  摘要：

  The intramolecular oxime olefin cycloaddition (IOOC) of proline and pipecolinic acid derivatives proceeds thermally with a high degree of stereoselectivity to provide a new route to functionalized pyrrolizidines, indolizidines, or quinolizidines. The ring closure proceeds with simultaneous stereoselective introduction of three or four stereocenters. Molecular mechanics calculations have been refined to accurately predict not only which stereoisomer is preferred but also the syn and anti coupling constants in these tricyclic molecules.

  DOI：

  10.1021/jo00008a038

文献信息

• HASSNER, ALFRED;MAURYA, RAKESH;PADWA, ALBERT;BULLOCK, WILLIAM H., J. ORG. CHEM., 56,(1991) N, C. 2775-2781
  作者：HASSNER, ALFRED、MAURYA, RAKESH、PADWA, ALBERT、BULLOCK, WILLIAM H.

  DOI：——

  日期：——
• Cycloadditions. 46. Thermally induced intramolecular oxime olefin cycloadditions leading to N-bridgehead systems. Stereochemistry and molecular mechanics calculations
  作者：Alfred Hassner、Rakesh Maurya、Albert Padwa、William H. Bullock

  DOI：10.1021/jo00008a038

  日期：1991.4

  The intramolecular oxime olefin cycloaddition (IOOC) of proline and pipecolinic acid derivatives proceeds thermally with a high degree of stereoselectivity to provide a new route to functionalized pyrrolizidines, indolizidines, or quinolizidines. The ring closure proceeds with simultaneous stereoselective introduction of three or four stereocenters. Molecular mechanics calculations have been refined to accurately predict not only which stereoisomer is preferred but also the syn and anti coupling constants in these tricyclic molecules.