Acetic acid 3-ethynyl-hept-6-enyl ester | 151655-17-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid 3-ethynyl-hept-6-enyl ester
• CAS: 151655-17-3
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: WXKVGJCVZSQROD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Acetic acid 3-ethynyl-hept-6-enyl ester 在 palladium diacetate 草酰氯 、 4 A molecular sieve 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 二甲基亚砜 、 9-bromo-9-borabicyclo[3.3.1]nonane 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 35.33h， 生成 2-Benzyl-7-methyl-1,3,4,4a,5,6-hexahydrocyclopenta[c]pyridine
  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：

  1-庚烯-6-炔 在 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 Acetic acid 3-ethynyl-hept-6-enyl ester
  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