N-tert-butyl-2,2-dibromopropanimine | 73968-64-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-tert-butyl-2,2-dibromopropanimine
• 英文别名: 2,2-dibromo-N-tert-butylpropan-1-imine
• CAS: 73968-64-6
• 化学式: C₇H₁₃Br₂N
• 分子量: 270.995
• InChiKey: RXBYIWYKTIPBMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-2,2-dibromopropanimine 生成 N-(2-bromoprop-1-enyl)-2-methylpropan-2-amine
  参考文献：
  名称：

  The reactions of organolithium compounds with α,α-dibromoaldimines and of lithium amide with α-brominated aldimines

  摘要：

  DOI：

  10.1016/s0040-4039(01)95396-1
• 作为产物：
  描述：

  N-(propylidene)-tert-butylamine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 16.0h， 以85%的产率得到N-tert-butyl-2,2-dibromopropanimine
  参考文献：
  名称：

  Synthesis and reactivity of alkenyl- and alkynyl-substituted β,β-dihalo-and β,β,β-trichloroamines

  摘要：

  beta,beta-Dihalo and beta,beta,beta-trichloroamines, obtained by Lewis acid-promoted Petasis-type reaction of alpha,alpha-dichlorinated and alpha,alpha,alpha-trichlorinated imines or reduction of alpha,alpha-dihaloaldimines, were subjected to a reactivity study and turned out to be remarkably stable compounds. In general, only the bases KO'Bu and NaOMe cause a 1,2-dehydrochlorination with formation of unsaturated alpha-chloroimines Or Unsaturated alpha,alpha-dichloroimines. Hydrolysis of the alpha-chloroimines with aqueous oxalic acid resulted in the formation of the corresponding unsaturated alpha-chloroketones. The reaction of simple beta,beta-dihaloamines with NaOMe and KO'Bu generated 2-haloprop-2-enylmines and 2,2-dimethoxypropylamines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.034

文献信息

• Reaction of O,O-dialkyldithiophosphoric acid with N-tert-butyl-2,2-dihalopropanimines
  作者：M. B. Gazizov、R. A. Khairullin、N. G. Aksenov、Yu. S. Kirillina、A. Yu. Bandikova

  DOI：10.1007/s11172-016-1422-z

  日期：2016.4

  O,O-Dialkyldithiophosphoric acid reacted with N-tert-butyl-2,2-dihalopropanimines to give iminium salt as a primary product, which further sequentially undergoes reaction with two equivalents of dithiophosphoric acid to initially reduce the C—X (X = Cl, Br) bond in the iminium salt and then nucleophilic replacement of the halogen atom with dialkoxydithiophosphate group. The final reaction products

  O,O-二烷基二硫代磷酸与 N-叔丁基-2,2-二卤代丙胺反应生成亚胺盐作为主要产物，其进一步依次与 2 当量的二硫代磷酸反应以初步还原 CX (X = Cl , Br) 键，然后用二烷氧基二硫代磷酸基团亲核取代卤素原子。最终反应产物是伯盐和双(二烷氧基硫代磷酰基)二硫化物的还原-取代产物。
• Reactions of N-tert-butyl-2,2-dichloro(dibromo)propanimines and O,O-dialkyldithiophosphoric acids
  作者：Mukattis B. Gazizov、Rafail A. Khairullin、Nikita G. Aksenov

  DOI：10.1016/j.tetlet.2015.11.095

  日期：2016.1

  The reactions of O,O-dialkyldithiophosphoric acids and N-tert-butyl-2,2-dichloro(dibromo)propanimines initially gave primary iminium salts. These salts subsequently reacted with another two acid molecules resulting firstly in reduction of the C-Hal bond and then nucleophilic substitution of the halogen by the (dialkoxythiophosphorylthio) group. The reactions studied resulted in formation of the reduction-substitution product of the primary iminium salt and bis(dialkoxythiophosphoryl)disulfide. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and reactivity of alkenyl- and alkynyl-substituted β,β-dihalo-and β,β,β-trichloroamines
  作者：Kourosch Abbaspour Tehrani、Sara Stas、Bart Lucas、Norbert De Kimpe

  DOI：10.1016/j.tet.2009.01.034

  日期：2009.3

  beta,beta-Dihalo and beta,beta,beta-trichloroamines, obtained by Lewis acid-promoted Petasis-type reaction of alpha,alpha-dichlorinated and alpha,alpha,alpha-trichlorinated imines or reduction of alpha,alpha-dihaloaldimines, were subjected to a reactivity study and turned out to be remarkably stable compounds. In general, only the bases KO'Bu and NaOMe cause a 1,2-dehydrochlorination with formation of unsaturated alpha-chloroimines Or Unsaturated alpha,alpha-dichloroimines. Hydrolysis of the alpha-chloroimines with aqueous oxalic acid resulted in the formation of the corresponding unsaturated alpha-chloroketones. The reaction of simple beta,beta-dihaloamines with NaOMe and KO'Bu generated 2-haloprop-2-enylmines and 2,2-dimethoxypropylamines. (C) 2009 Elsevier Ltd. All rights reserved.
• The reactions of organolithium compounds with α,α-dibromoaldimines and of lithium amide with α-brominated aldimines
  作者：Lucette Duhamel、Jean-Yves Valnot

  DOI：10.1016/s0040-4039(01)95396-1

  日期：1979.1