3-ethynylhept-6-en-1-ol | 151654-87-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-ethynylhept-6-en-1-ol
• CAS: 151654-87-4
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: IZXMSFVONASNRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  10.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-ethynylhept-6-en-1-ol 在 吡啶 、 4-二甲氨基吡啶 、 potassium carbonate 、 溶剂黄146 、 9-bromo-9-borabicyclo[3.3.1]nonane 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 3-(1-bromoethenyl)hept-6-en-1-ol
  参考文献：
  名称：

  Synthesis of bicyclic nitrogen compounds via tandem intramolecular Heck cyclization and subsequent trapping of intermediate .pi.-allylpalladium complexes

  摘要：

  Intramolecular palladium-mediated three-component cyclizations of substrates containing vinyl halide, olefin, and sulfonamide moieties to generate a diverse group of nitrogen heterocycles have been developed. The methodology has been applied to construction of both fused and bridged bicyclic systems. The strategy can also be used for spirocyclizations. This chemistry involves regiospecific generation of pi-allylpalladium complexes via Heck reactions of vinyl halides and simple olefins, followed by nucleophilic addition of sulfonamide anions to these intermediates.

  DOI：

  10.1021/jo00072a030
• 作为产物：
  描述：

  环氧乙烷 、 1-庚烯-6-炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以49%的产率得到3-ethynylhept-6-en-1-ol
  参考文献：
  名称：

  Synthesis of bicyclic nitrogen compounds via tandem intramolecular Heck cyclization and subsequent trapping of intermediate .pi.-allylpalladium complexes

  摘要：

  Intramolecular palladium-mediated three-component cyclizations of substrates containing vinyl halide, olefin, and sulfonamide moieties to generate a diverse group of nitrogen heterocycles have been developed. The methodology has been applied to construction of both fused and bridged bicyclic systems. The strategy can also be used for spirocyclizations. This chemistry involves regiospecific generation of pi-allylpalladium complexes via Heck reactions of vinyl halides and simple olefins, followed by nucleophilic addition of sulfonamide anions to these intermediates.

  DOI：

  10.1021/jo00072a030

文献信息

• A palladium-mediated tandem carbon-carbon bond forming method featuring nucleophilic substitution of intermediate π-allylpalladium complexes produced via the heck reaction
  作者：Christine S. Nylund、Daniel T. Smith、John M. Klopp、Steven M. Weinreb

  DOI：10.1016/0040-4020(95)00518-d

  日期：1995.8

  Carbon nucleophiles are alkylated with π-allylpalladium complexes formed by the palladium-catalyzed Heck reaction of a vinyl bromide and an olefin. This methodology achieves the consecutive formation of two carbon-carbon bonds in one simple operation and can be applied both inter- and intramolecularly. The rapid construction of functionalized carbobicyclic compounds is effected by the intramolecular

  碳亲核体被通过钯催化的乙烯基溴和烯烃的Heck反应形成的π-烯丙基铝络合物烷基化。该方法通过一次简单的操作即可连续形成两个碳-碳键，并且可以在分子内和分子内应用。官能化碳双环化合物的快速构建受此缩合的分子内形式影响。
• Synthesis of bicyclic nitrogen compounds via tandem intramolecular Heck cyclization and subsequent trapping of intermediate .pi.-allylpalladium complexes
  作者：G. Davis Harris、R. Jason Herr、Steven M. Weinreb

  DOI：10.1021/jo00072a030

  日期：1993.9

  Intramolecular palladium-mediated three-component cyclizations of substrates containing vinyl halide, olefin, and sulfonamide moieties to generate a diverse group of nitrogen heterocycles have been developed. The methodology has been applied to construction of both fused and bridged bicyclic systems. The strategy can also be used for spirocyclizations. This chemistry involves regiospecific generation of pi-allylpalladium complexes via Heck reactions of vinyl halides and simple olefins, followed by nucleophilic addition of sulfonamide anions to these intermediates.