Trimethyl-((Z)-undec-6-ene-1,4-diynyl)-silane | 667888-71-3

• 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: Trimethyl-((Z)-undec-6-ene-1,4-diynyl)-silane
• 英文别名: trimethyl-[(Z)-undec-6-en-1,4-diynyl]silane
• CAS: 667888-71-3
• 化学式: C₁₄H₂₂Si
• 分子量: 218.414
• InChiKey: QTDUTHQUFHTRKC-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  Trimethyl-((Z)-undec-6-ene-1,4-diynyl)-silane 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 正己烷 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 0.5h， 以70%的产率得到(Z,Z)-1-(trimethylsilyl)-4,6-undecadien-1-yne
  参考文献：
  名称：

  Metal-Catalyzed Coupling Reactions on an Olefin Template:  The Total Synthesis of (13E,15E,18Z,20Z)-1-Hydroxypentacosa- 13,15,18,20-tetraen-11-yn-4-one 1-Acetate

  摘要：

  The naturally occurring ant venom (13E,15E,18Z,20Z)-1-hydroxypentacosa-13,15,18,20-tetraen-11-yn-4-one 1-acetate was synthesized stereospecifically using a series of metal-mediated cross-coupling reactions. The use of the difunctional olefin template (E)-1-chloro-2-iodoethylene as the central, pseudosymmetrical building block facilitated a fully convergent and, thus, efficient strategy to prepare this polyunsaturated natural product.

  DOI：

  10.1021/jo035376k
• 作为产物：
  描述：

  (Z)-1-iodohex-1-ene 、 1-三甲基硅-1,4-戊二炔 在 溴乙烷 、 magnesium 、 zinc(II) chloride 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以80%的产率得到Trimethyl-((Z)-undec-6-ene-1,4-diynyl)-silane
  参考文献：
  名称：

  Metal-Catalyzed Coupling Reactions on an Olefin Template:  The Total Synthesis of (13E,15E,18Z,20Z)-1-Hydroxypentacosa- 13,15,18,20-tetraen-11-yn-4-one 1-Acetate

  摘要：

  The naturally occurring ant venom (13E,15E,18Z,20Z)-1-hydroxypentacosa-13,15,18,20-tetraen-11-yn-4-one 1-acetate was synthesized stereospecifically using a series of metal-mediated cross-coupling reactions. The use of the difunctional olefin template (E)-1-chloro-2-iodoethylene as the central, pseudosymmetrical building block facilitated a fully convergent and, thus, efficient strategy to prepare this polyunsaturated natural product.

  DOI：

  10.1021/jo035376k

文献信息

• Metal-Catalyzed Coupling Reactions on an Olefin Template:  The Total Synthesis of (13<i>E</i>,15<i>E</i>,18<i>Z</i>,20<i>Z</i>)-1-Hydroxypentacosa- 13,15,18,20-tetraen-11-yn-4-one 1-Acetate
  作者：Michael G. Organ、Haleh Ghasemi

  DOI：10.1021/jo035376k

  日期：2004.2.1

  The naturally occurring ant venom (13E,15E,18Z,20Z)-1-hydroxypentacosa-13,15,18,20-tetraen-11-yn-4-one 1-acetate was synthesized stereospecifically using a series of metal-mediated cross-coupling reactions. The use of the difunctional olefin template (E)-1-chloro-2-iodoethylene as the central, pseudosymmetrical building block facilitated a fully convergent and, thus, efficient strategy to prepare this polyunsaturated natural product.