N-tert-butyl-(4,4,4-trichloro-1-phenylbut-1-yn-3-yl)-amine | 1138741-54-4

• 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: N-tert-butyl-(4,4,4-trichloro-1-phenylbut-1-yn-3-yl)-amine
• 英文别名: N-tert-butyl-1,1,1-trichloro-4-phenylbut-3-yn-2-amine
• CAS: 1138741-54-4
• 化学式: C₁₄H₁₆Cl₃N
• 分子量: 304.647
• InChiKey: SLVOGIWYZPUHKY-UHFFFAOYSA-N

物化性质

• 沸点：
  336.7±42.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-(4,4,4-trichloro-1-phenylbut-1-yn-3-yl)-amine 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以84%的产率得到N-(4,4-dichloro-1-phenylbut-1-yn-3-ylidene)-tert-butylamine
  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
• 作为产物：
  描述：

  2-methyl-N-(2,2,2-trichloroethylidene)propan-2-amine 、 (苯乙炔基)三氟硼酸钾 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以76%的产率得到N-tert-butyl-(4,4,4-trichloro-1-phenylbut-1-yn-3-yl)-amine
  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

• An Indium(III)-Catalyzed Synthesis of 4,4-Dichloro-1-aryl-<i>N</i>-alkyl-1-yn-3-amines<i>via</i>an Intermolecular C(<i>sp</i>²)C(<i>sp</i>) Bond Formation
  作者：Chandi C. Malakar、Bert U. W. Maes、Kourosch Abbaspour Tehrani

  DOI：10.1002/adsc.201200680

  日期：2012.12.14

  This paper demonstrates an indium(III) triflate-catalyzed reaction of electron-deficient α,α-dichloroaldimines with terminal alkynes leading to a rapid and selective access to highly functionalized propargylic amines in good to excellent yields. The dichloromethylene moiety of the aldimine acts as an activating group to accomplish this transformation under very mild conditions.

  本文证明了缺电子的α，α-二氯醛亚胺与末端炔烃的三氟甲磺酸铟（III）催化反应可快速且选择性地获得高官能度的炔丙基胺，并具有良好的收率。该醛亚胺的二氯亚甲基部分充当活化基团，以在非常温和的条件下完成该转化。