diethyl 2-(2-butynyl)-2-(3,3-dimethoxypropyl)malonate | 927384-14-3

• 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: diethyl 2-(2-butynyl)-2-(3,3-dimethoxypropyl)malonate
• CAS: 927384-14-3
• 化学式: C₁₆H₂₆O₆
• 分子量: 314.379
• InChiKey: FZHCMDYPUXYJCN-UHFFFAOYSA-N

物化性质

• 沸点：
  381.1±42.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-(2-butynyl)-2-(3,3-dimethoxypropyl)malonate 在 水 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 diethyl 2-(2-butynyl)-2-(3-oxopropyl)malonate
  参考文献：
  名称：

  Butenolide Synthesis by Molybdenum-Mediated Hetero-Pauson−Khand Reaction of Alkynyl Aldehydes

  摘要：

  The highly reactive complex Mo(CO)(3)(DMF)(3) promotes the CO gas-free cyclocarbonylation of 1,5- and 1,6-alkynyl aldehydes under very mild reaction conditions to provide fused butenolides in good yields. This novel Mo-mediated hetero-Pauson-Khand reaction is very general with regard to the substitution at the alkyne terminus and tether (18 tested cases). Using readily available chiral alkynyl aldehydes, this procedure has been applied to the enantio- and stereoselective synthesis of highly substituted bicyclic butenolides, including an intermediate in natural product synthesis.

  DOI：

  10.1021/ja0684186
• 作为产物：
  描述：

  1-溴-2-丁炔 、 diethyl 2-(3,3-dimethoxypropyl)malonate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 以97%的产率得到diethyl 2-(2-butynyl)-2-(3,3-dimethoxypropyl)malonate
  参考文献：
  名称：

  Butenolide Synthesis by Molybdenum-Mediated Hetero-Pauson−Khand Reaction of Alkynyl Aldehydes

  摘要：

  The highly reactive complex Mo(CO)(3)(DMF)(3) promotes the CO gas-free cyclocarbonylation of 1,5- and 1,6-alkynyl aldehydes under very mild reaction conditions to provide fused butenolides in good yields. This novel Mo-mediated hetero-Pauson-Khand reaction is very general with regard to the substitution at the alkyne terminus and tether (18 tested cases). Using readily available chiral alkynyl aldehydes, this procedure has been applied to the enantio- and stereoselective synthesis of highly substituted bicyclic butenolides, including an intermediate in natural product synthesis.

  DOI：

  10.1021/ja0684186