(3Z,9Z)-1,12-bis(trimethylsilyl)dodeca-3,9-diene-1,11-diyne | 885041-55-4

• 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: (3Z,9Z)-1,12-bis(trimethylsilyl)dodeca-3,9-diene-1,11-diyne
• 英文别名: trimethyl-[(3Z,9Z)-12-trimethylsilyldodeca-3,9-dien-1,11-diynyl]silane
• CAS: 885041-55-4
• 化学式: C₁₈H₃₀Si₂
• 分子量: 302.607
• InChiKey: VNUVNHAJWFRLSE-XSYHWHKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  (3Z,9Z)-1,12-bis(trimethylsilyl)dodeca-3,9-diene-1,11-diyne 在 methyllithium lithium bromide 作用下， 以 乙醚 为溶剂， 生成 (3Z,9Z)-dodeca-3,9-diene-1,11-diyne 、 ((3Z,9Z)-Dodeca-3,9-diene-1,11-diynyl)-trimethyl-silane
  参考文献：
  名称：

  Synthesis of Marine Polyacetylenes Callyberynes A−C by Transition-Metal-Catalyzed Cross-Coupling Reactions to sp Centers

  摘要：

  Efficient total syntheses of the sponge-derived hydrocarbon polyacetylenes callyberynes A-C have been achieved using metal-catalyzed cross-coupling reactions of highly unsaturated 1,3-diyne fragments as the key steps, namely: Cadiot-Chodkiewicz reaction under Alamis optimized conditions (sp-sp), sequential Sonogashira reaction of a cis,cis-divinyl dihalide (sp(2)-sp), and Kumada-Corriu reaction of an unactivated alkyl iodide (sp(3)-sp). This last approach constitutes the first application of a metalcatalyzed sp(3)-sp Kumada-Corriu cross-coupling reaction to the synthesis of a natural product.

  DOI：

  10.1021/jo052609u
• 作为产物：
  描述：

  三甲基乙炔基硅 、 (1Z,7Z)-1,8-dibromoocta-1,7-diene 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 copper(l) iodide 作用下， 反应 1.5h， 以95%的产率得到(3Z,9Z)-1,12-bis(trimethylsilyl)dodeca-3,9-diene-1,11-diyne
  参考文献：
  名称：

  Synthesis of Marine Polyacetylenes Callyberynes A−C by Transition-Metal-Catalyzed Cross-Coupling Reactions to sp Centers

  摘要：

  Efficient total syntheses of the sponge-derived hydrocarbon polyacetylenes callyberynes A-C have been achieved using metal-catalyzed cross-coupling reactions of highly unsaturated 1,3-diyne fragments as the key steps, namely: Cadiot-Chodkiewicz reaction under Alamis optimized conditions (sp-sp), sequential Sonogashira reaction of a cis,cis-divinyl dihalide (sp(2)-sp), and Kumada-Corriu reaction of an unactivated alkyl iodide (sp(3)-sp). This last approach constitutes the first application of a metalcatalyzed sp(3)-sp Kumada-Corriu cross-coupling reaction to the synthesis of a natural product.

  DOI：

  10.1021/jo052609u

文献信息

• A short synthesis of (S)-(+)-siphonodiol
  作者：Benjamin W. Gung、Derek T. Craft、Jessica Truelove

  DOI：10.1016/j.tetasy.2007.05.034

  日期：2007.6

  A short synthesis of the enantiomer of the polyacetylenic natural product siphonodiol is described. The synthesis is based on the strategy of taking advantage of the hidden symmetry of the target molecule and minimizing the use of protecting groups, thereby reducing the total number of steps and increasing the overall efficiency. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Marine Polyacetylenes Callyberynes A−C by Transition-Metal-Catalyzed Cross-Coupling Reactions to sp Centers
  作者：Susana López、Francisco Fernández-Trillo、Pilar Midón、Luis Castedo、Carlos Saá

  DOI：10.1021/jo052609u

  日期：2006.3.31

  Efficient total syntheses of the sponge-derived hydrocarbon polyacetylenes callyberynes A-C have been achieved using metal-catalyzed cross-coupling reactions of highly unsaturated 1,3-diyne fragments as the key steps, namely: Cadiot-Chodkiewicz reaction under Alamis optimized conditions (sp-sp), sequential Sonogashira reaction of a cis,cis-divinyl dihalide (sp(2)-sp), and Kumada-Corriu reaction of an unactivated alkyl iodide (sp(3)-sp). This last approach constitutes the first application of a metalcatalyzed sp(3)-sp Kumada-Corriu cross-coupling reaction to the synthesis of a natural product.