(5R,7S,11S,12R)-16-ethyl-11-methyl-9,9-di(propan-2-yl)-8,10-dioxa-15-aza-9-silatetracyclo[11.2.1.05,15.07,14]hexadeca-1(16),13-dien-12-ol | 1001100-49-7

• 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: (5R,7S,11S,12R)-16-ethyl-11-methyl-9,9-di(propan-2-yl)-8,10-dioxa-15-aza-9-silatetracyclo[11.2.1.05,15.07,14]hexadeca-1(16),13-dien-12-ol
• CAS: 1001100-49-7
• 化学式: C₂₁H₃₅NO₃Si
• 分子量: 377.599
• InChiKey: QJQPFUQROGJMFS-POXQLVPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  43.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,7S,11S,12R)-16-ethyl-11-methyl-9,9-di(propan-2-yl)-8,10-dioxa-15-aza-9-silatetracyclo[11.2.1.05,15.07,14]hexadeca-1(16),13-dien-12-ol 、 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 scandium tris(trifluoromethanesulfonate) 作用下， 以 氘代乙腈 为溶剂， 以73%的产率得到(2R)-1-[(7R)-2-ethyl-11-azatricyclo[5.3.1.04,11]undeca-1,3-dien-3-yl]-2-[(5R,7S,11S,12S)-16-ethyl-11-methyl-9,9-di(propan-2-yl)-8,10-dioxa-15-aza-9-silatetracyclo[11.2.1.05,15.07,14]hexadeca-1(16),13-dien-12-yl]propan-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
• 作为产物：
  描述：

  (5R,7S,11S)-16-ethyl-11-methyl-9,9-di(propan-2-yl)-8,10-dioxa-15-aza-9-silatetracyclo[11.2.1.05,15.07,14]hexadeca-1(16),13-dien-12-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以58%的产率得到(5R,7S,11S,12R)-16-ethyl-11-methyl-9,9-di(propan-2-yl)-8,10-dioxa-15-aza-9-silatetracyclo[11.2.1.05,15.07,14]hexadeca-1(16),13-dien-12-ol
  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