3-butyl-3-cyano-6-methyl-1,4-cyclohexadiene | 671221-05-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-butyl-3-cyano-6-methyl-1,4-cyclohexadiene
• 英文别名: 2,5-Cyclohexadiene-1-carbonitrile, 1-butyl-4-methyl-；1-butyl-4-methylcyclohexa-2,5-diene-1-carbonitrile
• CAS: 671221-05-9
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: MGCBMUZACBYSLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  正溴丁烷 、 对甲苯腈 在 氨 、 lithium 、 叔丁醇 作用下， 以 四氢呋喃 、 氨 为溶剂， 以73%的产率得到3-butyl-3-cyano-6-methyl-1,4-cyclohexadiene
  参考文献：
  名称：

  芳烃的还原活化

  摘要：

  通过碱金属和烷基溴在液氨中的连续作用，苄腈、邻-、间-、对-甲苯腈和 1-萘甲腈的还原烷基化产生相应的烷基芳烃和 1-烷基-1-氰基环六-2,5-二烯。找到了目标合成指定产物的实验条件。基于芳香腈与 α,ω-二溴烷烃 Br(CH2)nBr (n = 3) 的双电子还原产物的相互作用合成 1-(ω-溴代烷基)-1-氰基环己-2,5-二烯的方法−5) 开发。

  DOI：

  10.1007/s11172-006-0366-0

文献信息

• Reductive Activation of Arenes: XVII. Effect of Methyl Substituent in Anion-radicals of Tolunitriles on the Mechanism of Their Reaction with Alkyl Bromides in Liquid Ammonia
  作者：T. A. Vaganova、V. D. Shteingarts

  DOI：10.1023/b:rujo.0000043725.48757.14

  日期：2004.5
• ——
  作者：T. A. Vaganova、E. V. Starokon'、V. D. Shteingarts

  DOI：10.1023/a:1026009329198

  日期：——

  Study of oxidation, protonation, and alkylation of the products obtained by one- and two-electron reduction of p-tolunitrile with sodium in liquid ammonia showed that these products are, respectively, p-tolunitrile radical anion and 1-cyano-4-methyl-2,5-cyclohexadienyl anion. The latter is formed by protonation of p-tolunitrile dianion with ammonia. The two-electron reduction involves protonation of p-tolunitrile dianion with initial p-tolunitrile, which gives rise to 4-cyanobenzyl anion. The yield of the latter depends on the order of mixing of the reactants. The anionic reduction products react with butyl bromide to afford products corresponding to ipso alkylation with respect to the cyano group, 4-butyltoluene and 3-butyl-3-cyano-6-methyl-1,4-cyclohexadiene, as well as the alkylation product at the benzylic position, 4-pentylbenzonitrile. The formation of 4-butyltoluene indicates the possibility for selective synthesis of p-alkyltoluenes by reductive alkylation of p-tolunitrile.
• Reductive activation of arenes
  作者：T. A. Vaganova、E. V. Panteleeva、P. S. Yuferov、Yu. V. Rebitva、V. D. Shteingarts

  DOI：10.1007/s11172-006-0366-0

  日期：2006.6

  Reductive alkylation of benzonitrile, ortho-, meta-, para-tolunitriles, and 1-naphthonitrile by sequential action of alkali metal and alkyl bromide in liquid ammonia results in corresponding alkylarenes and 1-alkyl-1-cyanocyclohexa-2,5-dienes. The experimental conditions for target synthesis of the specified products are found. A method of synthesis of 1-(ω-bromoalkyl)-1-cyanocyclohexa-2,5-dienes based

  通过碱金属和烷基溴在液氨中的连续作用，苄腈、邻-、间-、对-甲苯腈和 1-萘甲腈的还原烷基化产生相应的烷基芳烃和 1-烷基-1-氰基环六-2,5-二烯。找到了目标合成指定产物的实验条件。基于芳香腈与 α,ω-二溴烷烃 Br(CH2)nBr (n = 3) 的双电子还原产物的相互作用合成 1-(ω-溴代烷基)-1-氰基环己-2,5-二烯的方法−5) 开发。