N-tert-butyl-2,2-dichloropropanimine | 56906-31-1

• 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-dichloropropanimine
• 英文别名: N-t-butyl-2,2-dichloropropanimine；N-tert-butyl-2,2-dichloropropan-1-imine
• CAS: 56906-31-1
• 化学式: C₇H₁₃Cl₂N
• 分子量: 182.093
• InChiKey: HRCLIIOTPZIGFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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-dichloropropanimine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以72%的产率得到N-叔丁基-(2,2-二氯丙基)胺
  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：

  N-(propylidene)-tert-butylamine 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 生成 N-tert-butyl-2,2-dichloropropanimine
  参考文献：
  名称：

  5-Benzylidene-4-oxazolidinones potently inhibit biofilm formation in Methicillin-resistant Staphylococcus aureus

  摘要：

  对5-苄基亚甲基-4-噁唑烷酮的生物功能进行的调查显示，对耐甲氧西林金黄色葡萄球菌（MRSA）的生物膜形成具有剂量依赖性的抑制作用。

  DOI：

  10.1039/c7cc03626d

文献信息

• Metal-Free Synthesis of Chlorinated β-Amino Ketones<i>via</i>an Unexpected Reaction of Imines with Arylacetylenes in 1,1,1,3,3,3-Hexafluoro-2-propanol
  作者：Khushbu Kushwaha、Balazs Pinter、Syeda A. Shehzadi、Chandi C. Malakar、Christophe M. L. Vande Velde、Frank de Proft、Kourosch Abbaspour Tehrani

  DOI：10.1002/adsc.201500519

  日期：2016.1.7

  The metal‐free reaction of terminal arylacetylenes with α,α‐dichloroaldimines in 1,1,1,3,3,3‐hexafluoro‐2‐propanol as the sole solvent results in the rapid and selective formation of γ,γ‐dichloro‐β‐amino ketones. In this solvent the expected dichlorinated propargylamines and/or allylic amines are not formed. The dichloromethylene moiety of the aldimine acts as an activating group and is essential to

  末端芳基乙炔与α，α-二氯醛亚胺在1,1,1,3,3,3-六氟-2-丙醇中作为唯一溶剂的无金属反应导致γ，γ-二氯β-氨基酮。在该溶剂中，未形成预期的二氯化炔丙基胺和/或烯丙基胺。醛亚胺的二氯亚甲基部分用作活化基团，并且对于完成该转化是必不可少的。富电子乙炔导致最佳结果和工作以及与所有亚胺（具有或不α'-H在氮取代基），而缺电子乙炔仅与反应ñ -叔-丁基醛亚胺（无α'-H）。机理途径表明1,1,1,3,3,3-六氟-2-丙醇使醛亚胺质子化，该醛在速率确定步骤中将与芳基乙炔反应形成共振稳定的丙二烯阳离子，并被捕获通过HFIP分子产生烯醇醚，该烯醇醚迅速水解，仅提供β-氨基酮。使用DFT技术，我们发现第一个CC键形成步骤是速率确定步骤，并与约21 kcal mol -1的势垒相关。
• 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。
• De Kimpe,N. et al., Synthetic Communications, 1975, vol. 5, p. 269 - 274
  作者：De Kimpe,N. et al.

  DOI：——

  日期：——
• 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.
• Schepin, V. V.; Fotin, V. V.; Russkikh, N. Yu., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 4.1, p. 657 - 660
  作者：Schepin, V. V.、Fotin, V. V.、Russkikh, N. Yu.、Vikent'eva A. N.、Sinani, S. V.

  DOI：——

  日期：——