(5E)-1-trimethylsilyl-hept-5-ene-1,3-diyne | 811861-64-0

• 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: (5E)-1-trimethylsilyl-hept-5-ene-1,3-diyne
• 英文别名: [(E)-hept-5-en-1,3-diynyl]-trimethylsilane
• CAS: 811861-64-0
• 化学式: C₁₀H₁₄Si
• 分子量: 162.307
• InChiKey: FRMHPPPBXIPKTD-AATRIKPKSA-N

物化性质

• 沸点：
  191.1±23.0 °C(Predicted)
• 密度：
  0.856±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (5E)-1-trimethylsilyl-hept-5-ene-1,3-diyne 在 potassium fluoride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以93%的产率得到(5E)-hept-5-ene-1,3-diyne
  参考文献：
  名称：

  New stereoselective methodology for the synthesis of dihydroxerulin and xerulin, potent inhibitors of the biosynthesis of cholesterol

  摘要：

  A new stereoselective methodology for the synthesis of both dihydroxerulin and xerulin has been devised. The key step required cross-coupling reactions between the bromo trienyne, (1E,3E,5E)-l-bromo-8-trimethylsilyl-1,3,5-octatrien-7-yne and the appropriate conjugated diynes. The palladium-catalyzed tandem cross-coupling/cyclization reaction of the resulting polyenynes with (Z)-3-iodo-2-propenoic acid led directly to dihydroxerulin or xerulin with a high degree of stereoselectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.085
• 作为产物：
  描述：

  反-1-溴-1-丙烯 、 (Trimethylsilyl)butadiyne 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以82%的产率得到(5E)-1-trimethylsilyl-hept-5-ene-1,3-diyne
  参考文献：
  名称：

  New stereoselective methodology for the synthesis of dihydroxerulin and xerulin, potent inhibitors of the biosynthesis of cholesterol

  摘要：

  A new stereoselective methodology for the synthesis of both dihydroxerulin and xerulin has been devised. The key step required cross-coupling reactions between the bromo trienyne, (1E,3E,5E)-l-bromo-8-trimethylsilyl-1,3,5-octatrien-7-yne and the appropriate conjugated diynes. The palladium-catalyzed tandem cross-coupling/cyclization reaction of the resulting polyenynes with (Z)-3-iodo-2-propenoic acid led directly to dihydroxerulin or xerulin with a high degree of stereoselectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.085

文献信息

• Synthesis of naturally occurring polyacetylenes via a bis-silylated diyne
  作者：Vito Fiandanese、Daniela Bottalico、Giuseppe Marchese、Angela Punzi

  DOI：10.1016/j.tet.2006.03.043

  日期：2006.5

  A straightforward synthesis of a series of naturally occurring polyacetylenes has been developed, including the montiporynes A C ells, the atractylodin, with antibiotic at and C, possessing cytotoxic activity against several human solid tumor c activity against Escherichia coli, and triynes, which display insecticidal activities, starting from the readily available 1,4-bis(trimethylsilyl)-1,3-butadiyne. (c) 2006 Elsevier Ltd. All rights reserved.
• New stereoselective methodology for the synthesis of dihydroxerulin and xerulin, potent inhibitors of the biosynthesis of cholesterol
  作者：Vito Fiandanese、Daniela Bottalico、Giuseppe Marchese、Angela Punzi

  DOI：10.1016/j.tet.2004.09.085

  日期：2004.12

  A new stereoselective methodology for the synthesis of both dihydroxerulin and xerulin has been devised. The key step required cross-coupling reactions between the bromo trienyne, (1E,3E,5E)-l-bromo-8-trimethylsilyl-1,3,5-octatrien-7-yne and the appropriate conjugated diynes. The palladium-catalyzed tandem cross-coupling/cyclization reaction of the resulting polyenynes with (Z)-3-iodo-2-propenoic acid led directly to dihydroxerulin or xerulin with a high degree of stereoselectivity. (C) 2004 Elsevier Ltd. All rights reserved.