(Z)-10-trifluoromethanesulfonyloxy-1-triisopropylsilyldec-3-en-1-yne | 885041-68-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (Z)-10-trifluoromethanesulfonyloxy-1-triisopropylsilyldec-3-en-1-yne
• 英文别名: [(Z)-10-tri(propan-2-yl)silyldec-7-en-9-ynyl] trifluoromethanesulfonate
• CAS: 885041-68-9
• 化学式: C₂₀H₃₅F₃O₃SSi
• 分子量: 440.643
• InChiKey: COSVMGFOTOBGOQ-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-10-trifluoromethanesulfonyloxy-1-triisopropylsilyldec-3-en-1-yne 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 49.0h， 生成 (3Z,18Z)-henicosa-3,18-diene-1,8,10,20-tetrayne
  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：

  7-((tert-butyldiphenylsilyl)oxy)heptanal 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium diacetate 哌啶 、 吡啶 、 copper(l) iodide 、 四丁基氟化铵 、 三正丁基氢锡 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.58h， 生成 (Z)-10-trifluoromethanesulfonyloxy-1-triisopropylsilyldec-3-en-1-yne
  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.