N-(2.2.2-Trichlor-ethyliden)-propylamin | 16466-49-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2.2.2-Trichlor-ethyliden)-propylamin
• 英文别名: N-(2,2,2-trichloroethylidene)propylamine；propyl-(2,2,2-trichloro-ethylidene)-amine；2,2,2-trichloro-N-propylethanimine
• CAS: 16466-49-2
• 化学式: C₅H₈Cl₃N
• 分子量: 188.484
• InChiKey: FJNVZVFKVSLEBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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-(2.2.2-Trichlor-ethyliden)-propylamin 、 (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68%的产率得到N-(4,4,4-trichloro-1-phenylbut-1-yn-3-yl)propylamine
  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：

  正丙胺 、 三氯乙醛 生成 N-(2.2.2-Trichlor-ethyliden)-propylamin
  参考文献：
  名称：

  Borrmann,D.; Wegler,R., Chemische Berichte, 1967, vol. 100, # 6, p. 1814 - 1816

  摘要：

  DOI：

文献信息

• Lewis Acid Mediated Vinyl-Transfer Reaction of Alkynes to<i>N</i>-Alkylimines by Using the<i>N</i>-Alkyl Residue as a Sacrificial Hydrogen Donor
  作者：Chandi C. Malakar、Sara Stas、Wouter Herrebout、Kourosch Abbaspour Tehrani

  DOI：10.1002/chem.201300469

  日期：2013.10.11

  A variety of N‐alkyl‐α,α‐dichloroaldimines were vinylated by terminal acetylenes in the presence of Lewis acids such as In(OTf)3 or BF3⋅OEt2 and hexafluoroisopropanol (HFIP) as an additive. The reaction proceeds at ambient temperature and leads to geometrically pure allylic β,β‐dichloroamines. This approach is complementary to previously reported transition‐metal‐catalyzed vinyl‐transfer methods, which

  各种ñ -烷基- α，α-dichloroaldimines通过终端炔乙烯基化在Lewis的存在酸如在（OTF）3或BF 3 ⋅ OET 2和六氟异丙醇（HFIP）作为添加剂。反应在环境温度下进行，并生成几何上纯净的烯丙基β，β-二氯胺。这种方法是对先前报道的过渡金属催化的乙烯基转移方法的补充，后者不适用于脂族亚胺，仅限于含有吸电子氮取代基的亚胺。在本方法中，末端炔烃用作乙烯基残基的来源，而N亚胺的烷基部分起着牺牲氢供体的作用。该方法的另一个优点是不需要使用外部有毒或有害的还原剂或分子氢的事实。这种新方法很好地结合了C（sp 2）C（sp）键的形成，氢化物转移以及未活化的CN键的异常裂解，从而产生了功能化的伯烯丙基胺。进行了详细的实验研究，并通过DFT对该机制进行了计算。
• Jaeger,G., Chemische Berichte, 1972, vol. 105, p. 137 - 149
  作者：Jaeger,G.

  DOI：——

  日期：——
• 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.
• Borrmann,D.; Wegler,R., Chemische Berichte, 1967, vol. 100, # 6, p. 1814 - 1816
  作者：Borrmann,D.、Wegler,R.

  DOI：——

  日期：——