1,1,2,2-tetracyano-6-phenylspiro[2.4]octane | 668420-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1,2,2-tetracyano-6-phenylspiro[2.4]octane
• 英文别名: 1,1,2,2-tetracyano-6-phenylspiro[2.5]octane；6-Phenylspiro[2.5]octane-1,1,2,2-tetracarbonitrile
• CAS: 668420-55-1
• 化学式: C₁₈H₁₄N₄
• 分子量: 286.336
• InChiKey: FPYPOZFQYKAINM-UHFFFAOYSA-N

物化性质

• 熔点：
  171-173 °C
• 沸点：
  607.9±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 1,1,2,2-tetracyano-6-phenylspiro[2.4]octane 在 sodium bromide 作用下， 生成 2-amino-1,5-dicyano-4,4-dimethoxy-6,6-[(3-phenyl)pentamethylene]-3-azabicyclo[3.1.0]hex-2-ene 、 2-amino-1,5-dicyano-4,4-dimethoxy-6,6-[(3-phenyl)pentamethylene]-3-azabicyclo[3.1.0]hex-2-ene
  参考文献：
  名称：

  Electrocatalytic transformation of malononitrile and cycloalkylidenemalononitriles into spirotricyclic and spirotetracyclic compounds containing cyclopropane and pyrroline fragments

  摘要：

  Electrolysis of cycloalkylidenemalononitriles and malononitrile in MeOH in all undivided cell in the presence of the NaBr-NaOMe mediator system gives spirotricyclic compounds containing cyclopropane and pyrroline fragments in 50-77% yields. Spirobicyclic and spirotricyclic tetracyanocyclopropanes undergo electrolysis ill alcohols to afford spirotricyclic and spirotetracyclic products containing cyclopropane and pyrroline fragments ill 50-93% yields.

  DOI：

  10.1023/b:rucb.0000011885.10104.da
• 作为产物：
  描述：

  4-苯基环己酮 在 sodium bromide 作用下， 以 乙醇 为溶剂， 生成 1,1,2,2-tetracyano-6-phenylspiro[2.4]octane
  参考文献：
  名称：

  Electrocatalytic transformation of malononitrile and cycloalkylidenemalononitriles into spirobicyclic and spirotricyclic compounds containing 1,1,2,2-tetracyanocyclopropane fragment

  摘要：

  Electrolysis of malononitrile and cycloalkylidenemalononitriles in EtOH in an undivided cell in the presence of NaBr affords spirobicyclic Compounds containing a 1,1,2,2-tetra-cyanocyclopropane fragment in 50-88% yields.

  DOI：

  10.1023/b:rucb.0000011884.08799.a7

文献信息

• A new type of cascade reaction: direct conversion of carbonyl compounds and malononitrile into substituted tetracyanocyclopropanes
  作者：Michail N. Elinson、Anatolii N. Vereshchagin、Nikita O. Stepanov、Alexey I. Ilovaisky、Alexander Ya. Vorontsov、Gennady I. Nikishin

  DOI：10.1016/j.tet.2009.05.062

  日期：2009.8

  A new type of chemical cascade reaction was found: the direct formation of cyclopropanes from carbonyl compounds and C–H acid. The action of free halogen or active halogen containing compounds on a mixture of 1 equiv of carbonyl compound and 2 equiv of malononitrile in a basic alcohol solution results in the formation of substituted 1,1,2,2-tetracyanocyclopropanes in 15–80% yield. The latter are well-known

  发现了一种新型的化学级联反应：由羰基化合物和CHH酸直接形成环丙烷。游离卤素或含活性卤素的化合物在碱性醇溶液中对1当量羰基化合物和2当量丙二腈的混合物的作用导致形成取代的1,1,2,2-四氰基环丙烷，产率为15-80％ 。后者是用于不同双环杂系统的众所周知的前体，其中包括含有环丙烷环并具有不同类型药理活性的化合物。因此，直接从诸如醛，某些环酮或取代的环己酮和丙二腈之类的简单而合理的起始化合物中直接发现了一种新的，简单而有效的“一锅法”，以50-80％的产率取代四氰基环丙烷。
• Electrocatalytic transformation of malononitrile and cycloalkylidenemalononitriles into spirobicyclic and spirotricyclic compounds containing 1,1,2,2-tetracyanocyclopropane fragment
  作者：M. N. Elinson、S. K. Fedukovich、A. N. Vereshchagin、A. S. Dorofeev、D. E. Dmitriev、G. I. Nikishin

  DOI：10.1023/b:rucb.0000011884.08799.a7

  日期：2003.10

  Electrolysis of malononitrile and cycloalkylidenemalononitriles in EtOH in an undivided cell in the presence of NaBr affords spirobicyclic Compounds containing a 1,1,2,2-tetra-cyanocyclopropane fragment in 50-88% yields.
• Electrocatalytic transformation of malononitrile and cycloalkylidenemalononitriles into spirotricyclic and spirotetracyclic compounds containing cyclopropane and pyrroline fragments
  作者：M. N. Elinson、S. K. Fedukovich、T. A. Zaimovskaya、A. N. Vereshchagin、G. I. Nikishin

  DOI：10.1023/b:rucb.0000011885.10104.da

  日期：2003.10

  Electrolysis of cycloalkylidenemalononitriles and malononitrile in MeOH in all undivided cell in the presence of the NaBr-NaOMe mediator system gives spirotricyclic compounds containing cyclopropane and pyrroline fragments in 50-77% yields. Spirobicyclic and spirotricyclic tetracyanocyclopropanes undergo electrolysis ill alcohols to afford spirotricyclic and spirotetracyclic products containing cyclopropane and pyrroline fragments ill 50-93% yields.