2,4-甲桥-2,4-二去氢金刚烷 | 73586-31-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 2,4-甲桥-2,4-二去氢金刚烷
• 英文名称: 2,4-methano-2,4-didehydroadamantane
• 英文别名: 2,4-methano-2,4-dehydro-adamantane；pentacyclo[5.3.1.02,4.02,5.04,9]undecane
• CAS: 73586-31-9
• 化学式: C₁₁H₁₄
• 分子量: 146.232
• InChiKey: BYDHYGGDDSJOII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,4-甲桥-2,4-二去氢金刚烷 在 palladium on activated charcoal 氢气 作用下， 以 苯 为溶剂， 以90%的产率得到2-甲基金刚烷
  参考文献：
  名称：

  2,4-Methano-2,4-dehydroadamantane. A [3.1.1]propellane

  摘要：

  DOI：

  10.1021/ja00524a033
• 作为产物：
  描述：

  sodium;[(E)-(4-methylidene-2-adamantylidene)amino]-(4-methylphenyl)sulfonylazanide 以70%的产率得到
  参考文献：
  名称：

  MLINARIC-MAJERSKI K.; MAJERSKI Z., J. AMER. CHEM. SOC., 1980, NO 4, 1418-1419

  摘要：

  DOI：

文献信息

• Intramolecular γ C–H insertion vs. olefin cycloaddition in 4-methylene-2-adamantylidene and 8-methylene-2-noradamantylidene
  作者：Zdenko Majerski、Zdenko Hameršak、Katica Mlinarić-Majerski

  DOI：10.1039/c39850001830

  日期：——

  the olefin-cycloaddition product, while its higher homolouge 4-methylene-2-adamantylidene reacts exclusively by intramolecular cycloaddition to the olefinic bond yielding 2,4-methano-2,4-didehydroadamantane, a [3.1.1.]propellane.

  8-亚甲基-2-去甲金刚烷易于插入γC–H键中，从而获得6-亚甲基-2,4-二氢-去甲金刚烷而不是烯烃环加成产物，而其更高的同规卢比4-亚甲基-2-金刚烷仅与分子内环内加成到烯键上，得到2，4-亚甲基-2，4-二氢加氢金刚烷，一种[3.1.1。]丙炔。
• 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.
• The bond between inverted carbon atoms. Synthesis and chemistry of 2,4-methano-2,4-didehydroadamantane: a highly reactive [3.1.1]propellane
  作者：Katica Mlinaric-Majerski、Zdendo Majerski

  DOI：10.1021/ja00363a029

  日期：1983.11
• Free-radical reactions of a [3.1.1]propellane, 2,4-methano-2,4-didehydroadamantane
  作者：Kata Mlinaric-Majerski、Zdenko Majerski、Boris Rakvin、Zorica Veksli

  DOI：10.1021/jo00264a008

  日期：1989.2
• MLINARIC-MAJERSKI, K.;MAJERSKI, Z., J. AMER. CHEM. SOC., 1983, 105, N 25, 7389-7395
  作者：MLINARIC-MAJERSKI, K.、MAJERSKI, Z.

  DOI：——

  日期：——