2-methyl-2-(1,1,2,2-tetracyanoethyl)cyclohexanone | 385380-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-2-(1,1,2,2-tetracyanoethyl)cyclohexanone
• 英文别名: Ethane-1,1,2,2-tetracarbonitrile, 1-(1-methyl-2-oxocyclohexyl)-；1-(1-methyl-2-oxocyclohexyl)ethane-1,1,2,2-tetracarbonitrile
• CAS: 385380-97-2
• 化学式: C₁₃H₁₂N₄O
• 分子量: 240.264
• InChiKey: JHIYPVPZLNWXAB-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  508.9±45.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(1,1,2,2-tetracyanoethyl)cyclohexanone 在 氢碘酸 作用下， 以 水 为溶剂， 反应 2.0h， 以83%的产率得到8a-hydroxy-2-iodo-5-methyl-1,4,4a,5,6,7,8,8a-octahydroquinoline-3,4,4-tricarbonitrile
  参考文献：
  名称：

  四氟乙烯与2-取代的环己酮的反应

  摘要：

  Reactions of 2-methylcyclohexanone and menthone with tetracyanoethylene gave 2-(1,1,2,2-tetracyanoethyl)cyclohexanones which underwent quantitative transformation in the solid phase into 3,4-cyano-substituted 2-aminopyrans in 2 3 days at room temperature. 2-Methyl-2-(1,1,2,2-tetracyanoethyl)cyclohexanone reacted with hydroiodic acid to-afford 8a-hydroxy-2-iodo-4a-methyl-1,4,4a,5,6,7,8,8a-octahydroquinoline-3,4,4-tricarbonitrile. The reaction of 2,T-methylenedi(cyclohexanone) with tetracyanoethylene resulted in formation of 7-imino-4,5-tetramethylene-2 -oxo-6-oxabicyclo[3.2.1]octane-2-spiro-1'-cyclohexane-1,8,8-tricarbonitrile.

  DOI：

  10.1023/a:1020801612443
• 作为产物：
  描述：

  2-甲基环己酮 、 四氰基乙烯 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以90%的产率得到2-methyl-2-(1,1,2,2-tetracyanoethyl)cyclohexanone
  参考文献：
  名称：

  四氟乙烯与2-取代的环己酮的反应

  摘要：

  Reactions of 2-methylcyclohexanone and menthone with tetracyanoethylene gave 2-(1,1,2,2-tetracyanoethyl)cyclohexanones which underwent quantitative transformation in the solid phase into 3,4-cyano-substituted 2-aminopyrans in 2 3 days at room temperature. 2-Methyl-2-(1,1,2,2-tetracyanoethyl)cyclohexanone reacted with hydroiodic acid to-afford 8a-hydroxy-2-iodo-4a-methyl-1,4,4a,5,6,7,8,8a-octahydroquinoline-3,4,4-tricarbonitrile. The reaction of 2,T-methylenedi(cyclohexanone) with tetracyanoethylene resulted in formation of 7-imino-4,5-tetramethylene-2 -oxo-6-oxabicyclo[3.2.1]octane-2-spiro-1'-cyclohexane-1,8,8-tricarbonitrile.

  DOI：

  10.1023/a:1020801612443

文献信息

• Different Directions of the Reaction of 1-(2-Oxocycloalkyl)-ethane-1,1,2,2-tetracarbonitriles with Aqueous Ammonia
  作者：M. Yu. Belikov、O. V. Ershov

  DOI：10.1134/s1070428019040067

  日期：2019.4

  cycloalkanones, 1-(2-oxocycloalkyl)ethane-1,1,2,2-tetracarbonitriles, reacted with aqueous ammonia at room temperature to give, depending on the cycloalkane ring size and reaction conditions, three types of nitrogen-containing heterocyclic compounds. The reaction of tetracyanoethylene-cyclohexanone adducts with 20–25% aqueous ammonia afforded 10,11-diazatricyclo[5.3.2.01,6]-dodec-8-ene derivatives, whereas

  环烷酮，1-（2-氧代环烷基）乙烷-1,1,2,2-四甲腈的四乙氨基乙烯加合物在室温下与氨水反应，根据环烷烃环的大小和反应条件，得到三种类型的含氮化合物杂环化合物。四氰基乙烯-环己酮加合物与20-25％的氨水反应得到10,11-二氮杂三环[5.3.2.0 1,6 ] -dodec-8-ene衍生物，而它们的七元和八元类似物被转化为吡咯并[在相似条件下的3，4- c ]-吡啶。用10-15％的氨水处理1-（2-氧代环辛基）乙烷-1,1,2,2-四甲腈导致形成2,5-二氨基-3-（2-氧代环辛基）-3 H-吡咯-3,4-二碳腈为两种非对映异构体的混合物。
• Domino synthesis of 3-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-ene-4-carbonitriles
  作者：Sergey V. Fedoseev、Oleg V. Ershov、Mikhail Yu. Belikov、Konstantin V. Lipin、Ivan N. Bardasov、Oleg E. Nasakin、Viktor A. Tafeenko

  DOI：10.1016/j.tetlet.2013.02.043

  日期：2013.4

  The domino reactions of 4-oxoalkane-1,1,2,2-tetracarbonitriles with water afford 3-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-ene-4-carbonitriles in good yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Three-component synthesis of 2-halo-6-methoxy-5,6-dihydropyridine-3,4,4(1H)-tricarbonitriles
  作者：K. V. Lipin、O. V. Ershov

  DOI：10.1134/s1070428017110288

  日期：2017.11

  One-stage preparation method of 2-halo-6-methoxy-5,6-dihydropyridine-3,4,4(1H)-tricarbonitriles was developed, consisting in the reaction of 3,3-dialkyl-4-oxoalcane-1,1,2,2-tetracarbonitriles with hydrohalic acids in methanol.
• Selective quasi-hydrolysis of cyano group in 6-hydroxypiperidine-3,4,4-tricarbonitriles
  作者：K. V. Lipin、S. V. Fedoseev、O. V. Ershov、V. A. Tafeenko

  DOI：10.1134/s1070428017120077

  日期：2017.12

  Reactions of 3,3-dialkyl-4-oxoalkane-1,1,2,2-tetracarbonitriles with water in the presence of pyruvic acid are accompanied by selective quasi-hydrolysis of cyano groups in intermediate 6-hydroxy-piperidine-3,4,4-tricarbonitriles.
• Directed synthesis of alkyl-substitued pyrrolo[3,4-c]pyrrole-1,3,4,6-tetraones
  作者：S. V. Fedoseev、O. V. Ershov、M. Y. Belikov、K. V. Lipin、O. E. Nasakin、V. A. Tafeenko

  DOI：10.1134/s107042801311016x

  日期：2013.11

  Reactions of 3-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-ene-4-carbonitriles with aqueous hydrohalic acid led to the formation of alkyl-substituted pyrrolo[3,4-c]-pyrrole-1,3,4,6-tetraones.