N-methoxycarbonyl-2-allyl-2-(3-butenyl)pyrrolidine | 489475-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-methoxycarbonyl-2-allyl-2-(3-butenyl)pyrrolidine
• 英文别名: Methyl 2-(but-3-en-1-yl)-2-(prop-2-en-1-yl)pyrrolidine-1-carboxylate；methyl 2-but-3-enyl-2-prop-2-enylpyrrolidine-1-carboxylate
• CAS: 489475-37-8
• 化学式: C₁₃H₂₁NO₂
• 分子量: 223.315
• InChiKey: ACHWBTLIXJNVGA-UHFFFAOYSA-N

物化性质

• 沸点：
  282.9±9.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methoxycarbonyl-2-allyl-2-(3-butenyl)pyrrolidine 在 Grubbs catalyst first generation 作用下， 以 苯 为溶剂， 反应 2.5h， 以76%的产率得到N-methoxycarbonyl-1-azaspiro[4.5]dec-7-ene
  参考文献：
  名称：

  Electroauxiliary-Assisted Sequential Introduction of Two Carbon Nucleophiles on the Same α-Carbon of Nitrogen:  Application to the Synthesis of Spiro Compounds

  摘要：

  The sequential introduction of two carbon nucleophiles on the same alpha-carbon of nitrogen by using selective oxidative cleavage of two silyl groups as electroauxilialies has been accomplished. The combination of this expedient transformation and ring-closing metathesis enables reliable and straightforward syntheses of nitrogen-containing spiro compounds, such as cephalotaxine.

  DOI：

  10.1021/ja028663z
• 作为产物：
  描述：

  N-methoxycarbonyl-2,2-bis(trimethylsilyl)pyrrolidine 在 tetrabutylammonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 5.33h， 生成 N-methoxycarbonyl-2-allyl-2-(3-butenyl)pyrrolidine
  参考文献：
  名称：

  Electroauxiliary-Assisted Sequential Introduction of Two Carbon Nucleophiles on the Same α-Carbon of Nitrogen:  Application to the Synthesis of Spiro Compounds

  摘要：

  The sequential introduction of two carbon nucleophiles on the same alpha-carbon of nitrogen by using selective oxidative cleavage of two silyl groups as electroauxilialies has been accomplished. The combination of this expedient transformation and ring-closing metathesis enables reliable and straightforward syntheses of nitrogen-containing spiro compounds, such as cephalotaxine.

  DOI：

  10.1021/ja028663z

文献信息

• Electroauxiliary-Assisted Sequential Introduction of Two Carbon Nucleophiles on the Same α-Carbon of Nitrogen:  Application to the Synthesis of Spiro Compounds
  作者：Seiji Suga、Mitsuru Watanabe、Jun-ichi Yoshida

  DOI：10.1021/ja028663z

  日期：2002.12.1

  The sequential introduction of two carbon nucleophiles on the same alpha-carbon of nitrogen by using selective oxidative cleavage of two silyl groups as electroauxilialies has been accomplished. The combination of this expedient transformation and ring-closing metathesis enables reliable and straightforward syntheses of nitrogen-containing spiro compounds, such as cephalotaxine.