3,4-Hexadien-1-yl-acetat

• 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: 3,4-Hexadien-1-yl-acetat
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: RNDDZPYSIFUWND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3,4-Hexadien-1-yl-acetat 在 四(三苯基膦)钯 、 chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) 、 氧气 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 1.02h， 生成 (E)-ethyl 4-(5-hydroxy-3-(phenylimino)-5-propylisoxazolidin-2-yl)benzoate
  参考文献：
  名称：

  [3 + 2]-Annulations of N-Hydroxy Allenylamines with Nitrosoarenes: One-Pot Synthesis of Substituted Indole Products

  摘要：

  In the presence of O-2 and an IPrCuCl additive (5 mol %), [3 + 2]-annulation reactions of N-hydroxyaniline with nitrosobenzenes in cold toluene form isoxazolidin-5-ol derivatives. Heating the same reaction mixture with DBU in toluene affords highly functionalized indole products efficiently. This method provides short synthesis of several bioactive molecules including WIN 48098, WIN 53365, and JWH 015.

  DOI：

  10.1021/acs.orglett.5b03447
• 作为产物：
  描述：

  Hexa-2,3-dien-1-ol 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 为溶剂， 生成 3,4-Hexadien-1-yl-acetat
  参考文献：
  名称：

  [3 + 2]-Annulations of N-Hydroxy Allenylamines with Nitrosoarenes: One-Pot Synthesis of Substituted Indole Products

  摘要：

  In the presence of O-2 and an IPrCuCl additive (5 mol %), [3 + 2]-annulation reactions of N-hydroxyaniline with nitrosobenzenes in cold toluene form isoxazolidin-5-ol derivatives. Heating the same reaction mixture with DBU in toluene affords highly functionalized indole products efficiently. This method provides short synthesis of several bioactive molecules including WIN 48098, WIN 53365, and JWH 015.

  DOI：

  10.1021/acs.orglett.5b03447

文献信息

• Palladium-Catalyzed Dienylation of Haloalkynes using 2,3-Butadienyl Acetates: A Facile Access to (1Z)-1,2-Dihalo- 3-vinyl-1,3-dienes
  作者：Dongxu Chen、Xiaoyi Chen、Zenghui Lu、Haiting Cai、Jinbei Shen、Gangguo Zhu

  DOI：10.1002/adsc.201100113

  日期：2011.6

  A highly efficient and stereoselective method for the synthesis of (1Z)‐1,2‐dihalo‐3‐vinyl‐1,3‐dienes featuring palladium‐catalyzed coupling of haloalkynes and 2,3‐butadienyl acetates was developed. The resulting products were smoothly converted into cis‐1,2‐dihalostyrene derivatives using the Diels–Alder/aromatization sequence.

  开发了一种高效且立体选择性的合成（1 Z）-1,2-二卤代-3-乙烯基-1,3-二烯的方法，该方法具有钯催化的卤代炔烃和2,3-丁二烯基乙酸酯的偶联反应。使用Diels–Alder /芳香化顺序，将生成的产物平稳地转化为顺式1,2,2-二卤代苯乙烯衍生物。
• [3 + 2]-Annulations of <i>N</i>-Hydroxy Allenylamines with Nitrosoarenes: One-Pot Synthesis of Substituted Indole Products
  作者：Pankaj Sharma、Rai-Shung Liu

  DOI：10.1021/acs.orglett.5b03447

  日期：2016.2.5

  In the presence of O-2 and an IPrCuCl additive (5 mol %), [3 + 2]-annulation reactions of N-hydroxyaniline with nitrosobenzenes in cold toluene form isoxazolidin-5-ol derivatives. Heating the same reaction mixture with DBU in toluene affords highly functionalized indole products efficiently. This method provides short synthesis of several bioactive molecules including WIN 48098, WIN 53365, and JWH 015.