8-tert-butyldiphenylsilyloxy-1,1-dibromooct-1-ene | 885041-63-4

• 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: 8-tert-butyldiphenylsilyloxy-1,1-dibromooct-1-ene
• 英文别名: Tert-butyl-(8,8-dibromooct-7-enoxy)-diphenylsilane
• CAS: 885041-63-4
• 化学式: C₂₄H₃₂Br₂OSi
• 分子量: 524.411
• InChiKey: LOPGMFOLMMYMIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.14
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-tert-butyldiphenylsilyloxy-1,1-dibromooct-1-ene 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium diacetate 哌啶 、 吡啶 、 copper(l) iodide 、 正丁基锂 、 四丁基氟化铵 、 三正丁基氢锡 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 58.0h， 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：

  四溴化碳 、 7-((tert-butyldiphenylsilyl)oxy)heptanal 在 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以96%的产率得到8-tert-butyldiphenylsilyloxy-1,1-dibromooct-1-ene
  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.