dimethyl 2-(3-methylbut-3-enyl)-2-(prop-2-ynyl)malonate

• 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: dimethyl 2-(3-methylbut-3-enyl)-2-(prop-2-ynyl)malonate
• 英文别名: dimethyl 2-(3-methyl-3-butenyl)-2-(2-propynyl)malonate；Dimethyl 2-(3-methylbut-3-enyl)-2-prop-2-ynylpropanedioate；dimethyl 2-(3-methylbut-3-enyl)-2-prop-2-ynylpropanedioate
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: GEEBYQVGZHICBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(3-methylbut-3-enyl)-2-(prop-2-ynyl)malonate 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 为溶剂， 反应 3.0h， 以28%的产率得到5,5-dimethoxycarbonyl-7a-methyl-1,4,5,6,7,7a-hexahydroinden-2-one
  参考文献：
  名称：

  Investigation of Intramolecular Pauson-Khand Reaction of 2-Aryl-1,6- and 1-Methyl-1,7-enynes (exo-Olefins) and 1-Phenyl-1-octen-7-yne (endo-Olefin)

  摘要：

  The intramolecular Pauson-Khand reaction of various 2-aryl-1-hepten-6-ynes and its aza-derivatives (exo-olefins) efficiently produced arylbicyclo[3.3.0]octenones and azaoctenone bearing quaternary carbon centers at angular positions in good yields. Although a similar reaction of 2-phenyl-1-octen-7-yne (exo-olefin), which is a homologue of 2-phenyl-1-hepten-6-yne, did not take place, the reaction of the methyl derivatives smoothly proceeded. However, the reaction of regioisomeric 1-phenyl-1-octen-7-yne (endo-olefin) afforded the desired product in moderate yields.

  DOI：

  10.3987/com-03-9993
• 作为产物：
  描述：

  4-碘-2-甲基丁-1-烯 、 炔丙基丙二酸二甲酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82.3%的产率得到dimethyl 2-(3-methylbut-3-enyl)-2-(prop-2-ynyl)malonate
  参考文献：
  名称：

  Investigation of Intramolecular Pauson-Khand Reaction of 2-Aryl-1,6- and 1-Methyl-1,7-enynes (exo-Olefins) and 1-Phenyl-1-octen-7-yne (endo-Olefin)

  摘要：

  The intramolecular Pauson-Khand reaction of various 2-aryl-1-hepten-6-ynes and its aza-derivatives (exo-olefins) efficiently produced arylbicyclo[3.3.0]octenones and azaoctenone bearing quaternary carbon centers at angular positions in good yields. Although a similar reaction of 2-phenyl-1-octen-7-yne (exo-olefin), which is a homologue of 2-phenyl-1-hepten-6-yne, did not take place, the reaction of the methyl derivatives smoothly proceeded. However, the reaction of regioisomeric 1-phenyl-1-octen-7-yne (endo-olefin) afforded the desired product in moderate yields.

  DOI：

  10.3987/com-03-9993

文献信息

• Indium(III) Salt Promoted Intramolecular Addition of Allylsilanes to Unactivated Alkynes
  作者：Katsukiyo Miura、Akira Hosomi、Naoki Fujisawa、Sayaka Toyohara

  DOI：10.1055/s-2006-947348

  日期：2006.8

  stoichiometric or catalytic amount of a Lewis acidic indium(III) salt, allylsilanes reacted intramolecularly with unactivated terminal alkynes to give cyclized products in good to high yields. The fact that the reaction proceeded in a trans-addition mode suggests a reaction mechanism via electrophilic activation of the triple bond by the indium salt.

  在化学计量或催化量的路易斯酸性铟 (III) 盐存在下，烯丙基硅烷与未活化的末端炔烃发生分子内反应，以良好或高产率得到环化产物。反应以反式加成模式进行的事实表明反应机理是通过铟盐对三键的亲电活化。
• Investigation of Intramolecular Pauson-Khand Reaction of 2-Aryl-1,6- and 1-Methyl-1,7-enynes (exo-Olefins) and 1-Phenyl-1-octen-7-yne (endo-Olefin)
  作者：Miyuki Ishizaki、Hiroshi Satoh、Osamu Hoshino、Kiyoshi Nishitani、Hiroshi Hara

  DOI：10.3987/com-03-9993

  日期：——

  The intramolecular Pauson-Khand reaction of various 2-aryl-1-hepten-6-ynes and its aza-derivatives (exo-olefins) efficiently produced arylbicyclo[3.3.0]octenones and azaoctenone bearing quaternary carbon centers at angular positions in good yields. Although a similar reaction of 2-phenyl-1-octen-7-yne (exo-olefin), which is a homologue of 2-phenyl-1-hepten-6-yne, did not take place, the reaction of the methyl derivatives smoothly proceeded. However, the reaction of regioisomeric 1-phenyl-1-octen-7-yne (endo-olefin) afforded the desired product in moderate yields.