4-Isopropylidene-2-adamantanone | 134150-27-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Isopropylidene-2-adamantanone
• 英文别名: 4-propan-2-ylideneadamantan-2-one
• CAS: 134150-27-9
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: DFVHDIMACZAOMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-Isopropylidene-2-adamantanone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 14.0h， 生成 syn-4-Isopropylidene-2-adamantanol
  参考文献：
  名称：

  Synthesis and Reactivity Studies of 2,4-(Dimethylmethano)-2,4-didehydroadamantane: A Comparison with an Unsubstituted Analog

  摘要：

  We prepared 2,4-(dimethylmethano)-2,4-didehydroadamantane (1), agem-dimethyl[3.1.1]propellane, and systematically examined its chemical behavior in relation to its unsubstituted analogue 2,4-methane-2 ,4-didehydroadamantane (2). 2,4- (Dimethylmethano)-2,4-didehydroadamantane (1) was obtained in 70% yield by pyrolysis of the dry lithium salt of the tosylhydrazone derived from 4-isopropylidene-2-adamantanone (6) in vacuo. Propellane 1 is thermally more stable than 2, but its reactivity is considerably greater than that of 2. It is highly reactive toward electrophiles and free radicals. Propellane 1 also reacts with alcohols, dienes and oxygen but is less susceptible to polymerization than 2. Enhanced chemical reactivity of dimethyl[3.1.1]propellane 1, with respect to its unsubstituted analogue 2, is in accord with an increase in nucleophilicity of its central bond due to electron donation of the methyl groups.

  DOI：

  10.1021/jo00088a018
• 作为产物：
  描述：

  4-Hydroxyadamantan-2-on 在 lithium 作用下， 生成 4-Isopropylidene-2-adamantanone
  参考文献：
  名称：

  2,4-dimethylmethano-2,4-didehydroadamantane and its reactivity in relation to the unsubstituted analogue

  摘要：

  2,4-Dimethylmethano-2,4-didehydroadamantane (1) has been prepared and the gem-dimethyl substituent effects of propellane 1 in relation to its unsubstituted analogue 2 were studied. The reactivity of 1 is considerably greater than that of 2 due to the higher nucleophilicity of its central bond. However, 1 is thermally more stable than 2.

  DOI：

  10.1016/s0040-4039(00)74297-3

文献信息

• Synthesis and Reactivity Studies of 2,4-(Dimethylmethano)-2,4-didehydroadamantane: A Comparison with an Unsubstituted Analog
  作者：Kata Mlinaric-Majerski、Dunja Safar Cvitas、Jelena Veljkovic

  DOI：10.1021/jo00088a018

  日期：1994.5

  We prepared 2,4-(dimethylmethano)-2,4-didehydroadamantane (1), agem-dimethyl[3.1.1]propellane, and systematically examined its chemical behavior in relation to its unsubstituted analogue 2,4-methane-2 ,4-didehydroadamantane (2). 2,4- (Dimethylmethano)-2,4-didehydroadamantane (1) was obtained in 70% yield by pyrolysis of the dry lithium salt of the tosylhydrazone derived from 4-isopropylidene-2-adamantanone (6) in vacuo. Propellane 1 is thermally more stable than 2, but its reactivity is considerably greater than that of 2. It is highly reactive toward electrophiles and free radicals. Propellane 1 also reacts with alcohols, dienes and oxygen but is less susceptible to polymerization than 2. Enhanced chemical reactivity of dimethyl[3.1.1]propellane 1, with respect to its unsubstituted analogue 2, is in accord with an increase in nucleophilicity of its central bond due to electron donation of the methyl groups.
• 2,4-dimethylmethano-2,4-didehydroadamantane and its reactivity in relation to the unsubstituted analogue
  作者：Kata Mlinarić-Majerski、Dunja Šafar-Cvitaš、Zdenko Majerski

  DOI：10.1016/s0040-4039(00)74297-3

  日期：1991.3

  2,4-Dimethylmethano-2,4-didehydroadamantane (1) has been prepared and the gem-dimethyl substituent effects of propellane 1 in relation to its unsubstituted analogue 2 were studied. The reactivity of 1 is considerably greater than that of 2 due to the higher nucleophilicity of its central bond. However, 1 is thermally more stable than 2.