1-Chloro-3-(dimethylphenylsilyl)-2(E)-octene | 165259-99-4

• 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: 1-Chloro-3-(dimethylphenylsilyl)-2(E)-octene
• 英文别名: [(E)-1-chlorooct-2-en-3-yl]-dimethyl-phenylsilane
• CAS: 165259-99-4
• 化学式: C₁₆H₂₅ClSi
• 分子量: 280.913
• InChiKey: PUVVXEZERUFLRB-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-Chloro-3-(dimethylphenylsilyl)-2(E)-octene 在 四(三苯基膦)钯 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (6Z,9Z)-heptadeca-6,9-diene
  参考文献：
  名称：

  Stereoselective Synthesis of 1,4-Dienes. Application to the Preparation of Insect Pheromones (3Z,6Z)-Dodeca-3,6-dien-1-ol and (4E,7Z)-Trideca-4,7-dienyl Acetate

  摘要：

  Stereoselective synthesis of Z,E and Z,Z-1,4-dienes has been achieved by the cross-coupling of allylic substrates with vinyl organometallic reagents. Key to this strategy was the development of a method for regiospecific incorporation of a tri-n-butylstannyl group in the gamma-position of the allylic cross-coupling partner. The steric bulk of this moiety ensures the stereochemical integrity of the allylic double bond throughout the coupling sequence and is easily replaced by hydrogen in the coupled product. This strategy has been applied to the synthesis of the termite trail marker pheromone 22 and the leafminer moth sex pheromone 28.

  DOI：

  10.1021/jo00119a043
• 作为产物：
  描述：

  2-辛炔-1-醇 在 四氯化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.75h， 生成 1-Chloro-3-(dimethylphenylsilyl)-2(E)-octene
  参考文献：
  名称：

  Stereoselective Synthesis of 1,4-Dienes. Application to the Preparation of Insect Pheromones (3Z,6Z)-Dodeca-3,6-dien-1-ol and (4E,7Z)-Trideca-4,7-dienyl Acetate

  摘要：

  Stereoselective synthesis of Z,E and Z,Z-1,4-dienes has been achieved by the cross-coupling of allylic substrates with vinyl organometallic reagents. Key to this strategy was the development of a method for regiospecific incorporation of a tri-n-butylstannyl group in the gamma-position of the allylic cross-coupling partner. The steric bulk of this moiety ensures the stereochemical integrity of the allylic double bond throughout the coupling sequence and is easily replaced by hydrogen in the coupled product. This strategy has been applied to the synthesis of the termite trail marker pheromone 22 and the leafminer moth sex pheromone 28.

  DOI：

  10.1021/jo00119a043

文献信息

• Stereoselective Synthesis of 1,4-Dienes. Application to the Preparation of Insect Pheromones (3Z,6Z)-Dodeca-3,6-dien-1-ol and (4E,7Z)-Trideca-4,7-dienyl Acetate
  作者：Michael W. Hutzinger、Allan C. Oehlschlager

  DOI：10.1021/jo00119a043

  日期：1995.7

  Stereoselective synthesis of Z,E and Z,Z-1,4-dienes has been achieved by the cross-coupling of allylic substrates with vinyl organometallic reagents. Key to this strategy was the development of a method for regiospecific incorporation of a tri-n-butylstannyl group in the gamma-position of the allylic cross-coupling partner. The steric bulk of this moiety ensures the stereochemical integrity of the allylic double bond throughout the coupling sequence and is easily replaced by hydrogen in the coupled product. This strategy has been applied to the synthesis of the termite trail marker pheromone 22 and the leafminer moth sex pheromone 28.