[(3S,3aS,10aS,10bR)-7-bromo-10a-(2-methoxyethoxymethoxy)-3a-methyl-8-methylidene-2,3,4,9,10,10b-hexahydro-1H-cyclohepta[e]inden-3-yl]oxy-tert-butyl-dimethylsilane | 1092775-32-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [(3S,3aS,10aS,10bR)-7-bromo-10a-(2-methoxyethoxymethoxy)-3a-methyl-8-methylidene-2,3,4,9,10,10b-hexahydro-1H-cyclohepta[e]inden-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1092775-32-0
• 化学式: C₂₆H₄₃BrO₄Si
• 分子量: 527.615
• InChiKey: DIPQBQXCMAODMU-MFYWSIJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  triethyl-[(E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoxy]silane 、 [(3S,3aS,10aS,10bR)-7-bromo-10a-(2-methoxyethoxymethoxy)-3a-methyl-8-methylidene-2,3,4,9,10,10b-hexahydro-1H-cyclohepta[e]inden-3-yl]oxy-tert-butyl-dimethylsilane 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以84%的产率得到C₃₅H₆₂O₅Si₂
  参考文献：
  名称：

  Enantioselective Synthesis of (+)-Cortistatin A, a Potent and Selective Inhibitor of Endothelial Cell Proliferation

  摘要：

  This manuscript describes an enantioselective synthesis of the naturally occurring inhibitor of endothelial cell proliferation, cortistatin A. Key steps of the synthesis are a silicate-directed elimination/ring expansion reaction and a highly diastereoselective aza-Prins cyclization with a subsequent transannular etherification.

  DOI：

  10.1021/ja8071918
• 作为产物：
  描述：

  tert-butyl-[[(1S,2R,5S,6S)-11,11-dibromo-1-(2-methoxyethoxymethoxy)-6-methyl-12-[[methyl-di(propan-2-yloxy)silyl]methyl]-5-tetracyclo[7.5.0.02,6.010,12]tetradec-8-enyl]oxy]-dimethylsilane 在 TASF 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以500 mg的产率得到[(3S,3aS,10aS,10bR)-7-bromo-10a-(2-methoxyethoxymethoxy)-3a-methyl-8-methylidene-2,3,4,9,10,10b-hexahydro-1H-cyclohepta[e]inden-3-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Enantioselective Synthesis of (+)-Cortistatin A, a Potent and Selective Inhibitor of Endothelial Cell Proliferation

  摘要：

  This manuscript describes an enantioselective synthesis of the naturally occurring inhibitor of endothelial cell proliferation, cortistatin A. Key steps of the synthesis are a silicate-directed elimination/ring expansion reaction and a highly diastereoselective aza-Prins cyclization with a subsequent transannular etherification.

  DOI：

  10.1021/ja8071918

文献信息

• [EN] CORTISTATIN ANALOGUES AND SYNTHESES THEROF<br/>[FR] ANALOGUES DE CORTISTATINE ET LEURS SYNTHÈSES
  申请人：HARVARD COLLEGE

  公开号：WO2010024930A3

  公开（公告）日：2010-07-01
• Enantioselective Synthesis of (+)-Cortistatin A, a Potent and Selective Inhibitor of Endothelial Cell Proliferation
  作者：Hong Myung Lee、Cristina Nieto-Oberhuber、Matthew D. Shair

  DOI：10.1021/ja8071918

  日期：2008.12.17

  This manuscript describes an enantioselective synthesis of the naturally occurring inhibitor of endothelial cell proliferation, cortistatin A. Key steps of the synthesis are a silicate-directed elimination/ring expansion reaction and a highly diastereoselective aza-Prins cyclization with a subsequent transannular etherification.