(5Z,11Z)-2,15-dimethylhexadeca-5,11-diene-3,13-diyne-2,15-diol | 885041-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5Z,11Z)-2,15-dimethylhexadeca-5,11-diene-3,13-diyne-2,15-diol
• 英文别名: (5Z,11Z)-2,15-dimethylhexadeca-5,11-dien-3,13-diyne-2,15-diol
• CAS: 885041-57-6
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: WEJBPAQRVBIYSP-HWAYABPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5Z,11Z)-2,15-dimethylhexadeca-5,11-diene-3,13-diyne-2,15-diol 在 哌啶 、 氢氧化钾 、 copper(l) iodide 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 (5Z,11Z)-2-methyl-23-triisopropylsilyltricosa-5,11-diene-3,13,15,20,22-pentayn-2-ol
  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：

  2-甲基-3-丁炔-2-醇 、 (1Z,7Z)-1,8-dibromoocta-1,7-diene 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 copper(l) iodide 作用下， 反应 1.0h， 以84%的产率得到(5Z,11Z)-2,15-dimethylhexadeca-5,11-diene-3,13-diyne-2,15-diol
  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

• 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.