(4aR)-1-(1-ethyl-3,4,4a,5,6,7-hexahydropyrrolo[2,1,5-cd]indolizin-2-yl)propan-1-one | 269077-60-3

• 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: (4aR)-1-(1-ethyl-3,4,4a,5,6,7-hexahydropyrrolo[2,1,5-cd]indolizin-2-yl)propan-1-one
• 英文别名: (4aR)-1-(1-ethyl-3,4,4a,5,6,7-hexahydropyrrolo[2,1,5-cd]indolizin2-yl)propanone；(4aR)-1-(1-Ethyl-3,4,4a,5,6,7-hexahydro-pyrrolo[2,1,5-cd]indolizin-2-yl)-propan-1-one；1-[(7R)-2-ethyl-11-azatricyclo[5.3.1.04,11]undeca-1,3-dien-3-yl]propan-1-one
• CAS: 269077-60-3
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: IKMZOZSBTXYGEZ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4aR)-1-(1-ethyl-3,4,4a,5,6,7-hexahydropyrrolo[2,1,5-cd]indolizin-2-yl)propan-1-one 在 三氟甲磺酸 作用下， 以 乙二醇 、 1,2-二氯乙烷 为溶剂， 以100%的产率得到(7aR)-4-ethyl-1,2,5,6,7,7a-hexahydro-1H-pyrrolo[2,1,5-cd]indolizine
  参考文献：
  名称：

  Dimerization of functional pyrroloindolizines for the synthesis of complex myrmicarin alkaloids

  摘要：

  The union of functionalized pyrroloindolizines for the synthesis of heterodimeric products relevant to myrmicarin alkaloids is described. Design and synthesis of tricyclic substrates and new methods for their union enable the investigation of late-stage cyclopentannulation strategies. The rapid assembly of dimeric structures using unique modes of pyrroloindolizine reactivity presents a concise approach to the dimeric myrmicarins and relevant derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.006
• 作为产物：
  描述：

  (5R)-(5,6,7,8-tetrahydroindolizin-5-yl)acetic acid 在 lithium aluminium tetrahydride 、 三氯化铝 、 三氟化硼乙醚 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 甲苯 为溶剂， 反应 48.67h， 生成 (4aR)-1-(1-ethyl-3,4,4a,5,6,7-hexahydropyrrolo[2,1,5-cd]indolizin-2-yl)propan-1-one
  参考文献：
  名称：

  First Synthesis of Nonracemic (R)-(+)-Myrmicarin 217

  摘要：

  DOI：

  10.1021/jo9918697

文献信息

• Enantioselective Total Synthesis of Tricyclic Myrmicarin Alkaloids
  作者：Mohammad Movassaghi、Alison E. Ondrus

  DOI：10.1021/ol051629f

  日期：2005.9.1

  [reaction: see text] An enantioselective gram-scale synthesis of a key dihydroindolizine intermediate for the preparation of myrmicarin alkaloids is described. Key transformations in this convergent approach include a stereospecific palladium-catalyzed N-vinylation of a pyrrole with a vinyl triflate, a copper-catalyzed enantioselective conjugate reduction of a beta-pyrrolyl enoate, and a regioselective

  [反应：见正文] 描述了用于制备 myrmicarin 生物碱的关键二氢中氮茚中间体的对映选择性克级合成。这种收敛方法的关键转化包括吡咯与三氟甲磺酸乙烯酯的立体特异性钯催化的 N-乙烯基化、铜催化的 β-吡咯基烯酸酯的对映选择性共轭还原以及区域选择性弗里德尔-克来福特反应。介绍了 (4aR)-myrmicarins 215A、215B 和 217 以及它们各自的 C4a-差向异构体的光学活性和异构纯样品的合成。
• 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.
• Dimerization of (+)-myrmicarin 215B. A potential biomimetic approach to complex myrmicarin alkaloids
  作者：Alison E. Ondrus、Mohammad Movassaghi

  DOI：10.1016/j.tet.2006.01.108

  日期：2006.5

  The acid promoted diastereoselective dimerization of myrmicarin 215B is described. The reactivity of these sensitive alkaloids, structural assignment, and a possible mechanism for the observed dimerization is discussed. These finding raise the intriguing possibility of the synthesis of the highly sensitive myrmicarin alkaloids based on a strategy involving the direct dimerization of functional tricyclic myrmicarin derivatives. (c) 2006 Elsevier Ltd. All rights reserved.
• First Synthesis of Nonracemic (<i>R</i>)-(+)-Myrmicarin 217
  作者：Babak Sayah、Nadia Pelloux-Léon、Yannick Vallée

  DOI：10.1021/jo9918697

  日期：2000.5.1
• Dimerization of functional pyrroloindolizines for the synthesis of complex myrmicarin alkaloids
  作者：Alison E. Ondrus、H. Ümit Kaniskan、Mohammad Movassaghi

  DOI：10.1016/j.tet.2010.04.006

  日期：2010.6

  The union of functionalized pyrroloindolizines for the synthesis of heterodimeric products relevant to myrmicarin alkaloids is described. Design and synthesis of tricyclic substrates and new methods for their union enable the investigation of late-stage cyclopentannulation strategies. The rapid assembly of dimeric structures using unique modes of pyrroloindolizine reactivity presents a concise approach to the dimeric myrmicarins and relevant derivatives. (C) 2010 Elsevier Ltd. All rights reserved.