8-But-3-enyl-1,5,6,7-tetrahydro-2H-indolizin-3-one | 252041-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 8-But-3-enyl-1,5,6,7-tetrahydro-2H-indolizin-3-one
• 英文别名: 8-but-3-enyl-2,5,6,7-tetrahydro-1H-indolizin-3-one
• CAS: 252041-46-6
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: KRDGHCKMIMSBLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-But-3-enyl-1,5,6,7-tetrahydro-2H-indolizin-3-one 在 甲酸 、 氨 作用下， 以 甲醇 为溶剂， 反应 17.5h， 以92%的产率得到(7aR,10S,11aS)-10-hydroxy-1,2,5,6,7,7a,8,9,10,11-decahydropyrrolo[2,1-j]quinolin-3-one
  参考文献：
  名称：

  A Kulinkovich Entry into Tertiary N-Acyliminium Ion Chemistry

  摘要：

  [GRAPHICS]Subjection of N-alkenylimides to Kulinkovich cyclopropanation conditions led to different types of N,O-acetals, which were used as precursors for tertiary N-acyliminium ion chemistry. In this way, a variety of bi- and tricyclic lactams were efficiently synthesized.

  DOI：

  10.1021/ol990866d
• 作为产物：
  描述：

  1-(pent-4-en-1-yl)pyrrolidine-2,5-dione 在 三异丙氧基氯化钛 、 三氟化硼乙醚 、 Cyclopentylmagnesium chloride 作用下， 以 二氯甲烷 为溶剂， 生成 8-But-3-enyl-1,5,6,7-tetrahydro-2H-indolizin-3-one
  参考文献：
  名称：

  A Kulinkovich Entry into Tertiary N-Acyliminium Ion Chemistry

  摘要：

  [GRAPHICS]Subjection of N-alkenylimides to Kulinkovich cyclopropanation conditions led to different types of N,O-acetals, which were used as precursors for tertiary N-acyliminium ion chemistry. In this way, a variety of bi- and tricyclic lactams were efficiently synthesized.

  DOI：

  10.1021/ol990866d

文献信息

• Synthetic Studies Toward caphalotaxine: Functionalization of Tertiary N-Acylhemiaminals by Nazarov Cyclization
  作者：Se-Ho Kim、Jin Kun Cha

  DOI：10.1055/s-2000-8711

  日期：——

  Functionalization of bicyclic N-acylhemiaminals, which are readily available by titanium-mediated intramolecular coupling of vinyl-tethered imides, has been achieved by use of the Nazarov cyclization to construct the carbon-carbon bond at the quaternary center. This synthetic strategy allows rapid entry to the key structural elements of cephalotaxine.

  已实现对双环N-酰基半胺的功能化，这些化合物可以通过钛介导的乙烯连接的酰胺的分子内偶联容易获得，使用Nazarov环化反应在四级中心构建碳-碳键。这一合成策略使我们能够快速进入颅税素的关键结构元素。