1,3-bis-(1-ethyl-3,4,4a,5,6,7-hexahydro-pyrrolo[2,1,5-cd]indolizin-2-yl)-4-methoxy-2-methyl-pent-3-en-1-one | 1001100-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯嗪
• 英文名称: 1,3-bis-(1-ethyl-3,4,4a,5,6,7-hexahydro-pyrrolo[2,1,5-cd]indolizin-2-yl)-4-methoxy-2-methyl-pent-3-en-1-one
• 英文别名: (Z)-1,3-bis[(7R)-2-ethyl-11-azatricyclo[5.3.1.04,11]undeca-1,3-dien-3-yl]-4-methoxy-2-methylpent-3-en-1-one
• CAS: 1001100-60-2
• 化学式: C₃₁H₄₂N₂O₂
• 分子量: 474.687
• InChiKey: BRYOXIQSAHNUHH-RSHITWPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  36.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-bis-(1-ethyl-3,4,4a,5,6,7-hexahydro-pyrrolo[2,1,5-cd]indolizin-2-yl)-4-methoxy-2-methyl-pent-3-en-1-one 在 4-甲基苯磺酸吡啶 作用下， 以 水 、 乙腈 、 苯 为溶剂， 反应 0.5h， 以70%的产率得到1,3-bis-(1-ethyl-3,4,4a,5,6,7-hexahydro-pyrrolo[2,1,5-cd]indolizin-2-yl)-2-methyl-pentane-1,4-dione
  参考文献：
  名称：

  Efficient and Stereoselective Dimerization of Pyrroloindolizine Derivatives Inspired by a Hypothesis for the Biosynthesis of Complex Myrmicarin Alkaloids

  摘要：

  Pyrroloindolizine derivatives participate in efficient and stereoselective homo- and heterodimerization reactions upon treatment with Bronsted or Lewis acids. The distinctive ability of pyrroloindolizines to act as azafulvenium ion precursors provides direct access to both heptacyclic and hexacyclic dimeric products. The inherent reactivity of these structures suggests a concise synthesis of complex myrmicarin alkaloids, via dimerization of pyrroloindolizines, and may have implications for the biosynthesis of these intriguing alkaloids.

  DOI：

  10.1021/jo701981q
• 作为产物：
  描述：

  1-(1-ethyl-3,4,4a,5,6,7-hexahydro-pyrrolo[2,1,5-cd]indolizin-2-yl)-2-methoxy-propan-1-one 、 Z-4-ethyl-3-[1-(triisopropyl-silanyloxy)propenyl]-1,2,5,6,7,7a-hexahydro-pyrrolo[2,1,5-cd]indolizine 在 2,6-二叔丁基-4-甲基吡啶 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到1,3-bis-(1-ethyl-3,4,4a,5,6,7-hexahydro-pyrrolo[2,1,5-cd]indolizin-2-yl)-4-methoxy-2-methyl-pent-3-en-1-one
  参考文献：
  名称：

  Efficient and Stereoselective Dimerization of Pyrroloindolizine Derivatives Inspired by a Hypothesis for the Biosynthesis of Complex Myrmicarin Alkaloids

  摘要：

  Pyrroloindolizine derivatives participate in efficient and stereoselective homo- and heterodimerization reactions upon treatment with Bronsted or Lewis acids. The distinctive ability of pyrroloindolizines to act as azafulvenium ion precursors provides direct access to both heptacyclic and hexacyclic dimeric products. The inherent reactivity of these structures suggests a concise synthesis of complex myrmicarin alkaloids, via dimerization of pyrroloindolizines, and may have implications for the biosynthesis of these intriguing alkaloids.

  DOI：

  10.1021/jo701981q

文献信息

• Efficient and Stereoselective Dimerization of Pyrroloindolizine Derivatives Inspired by a Hypothesis for the Biosynthesis of Complex Myrmicarin Alkaloids
  作者：Mohammad Movassaghi、Alison E. Ondrus、Bin Chen

  DOI：10.1021/jo701981q

  日期：2007.12.1

  Pyrroloindolizine derivatives participate in efficient and stereoselective homo- and heterodimerization reactions upon treatment with Bronsted or Lewis acids. The distinctive ability of pyrroloindolizines to act as azafulvenium ion precursors provides direct access to both heptacyclic and hexacyclic dimeric products. The inherent reactivity of these structures suggests a concise synthesis of complex myrmicarin alkaloids, via dimerization of pyrroloindolizines, and may have implications for the biosynthesis of these intriguing alkaloids.