N-isopropyl-2-chloro-2-methyl-1-phenylpropan-1-imine | 137208-24-3

• 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-isopropyl-2-chloro-2-methyl-1-phenylpropan-1-imine
• 英文别名: N-isopropyl-2-methyl-1-phenyl-2-chloropropanimine；2-chloro-2-methyl-1-phenyl-N-propan-2-ylpropan-1-imine
• CAS: 137208-24-3
• 化学式: C₁₃H₁₈ClN
• 分子量: 223.746
• InChiKey: XSKXIOLZEXOZRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-isopropyl-2-chloro-2-methyl-1-phenylpropan-1-imine 、 二硫代磷酸-O,O-二(1-甲基乙基)酯 以 二氯甲烷 为溶剂， 反应 72.0h， 以6.3 mg的产率得到N-isopropyl-2-methyl-1-phenyl-1-propaniminium chloride
  参考文献：
  名称：

  Reaction of P(IV) Dithio Acids with N-Alkyl-α-chloroketimines

  摘要：

  Effect of the substituent on the imine carbon atom on the result of the reaction of P(IV) dithio acids with N-Alkyl--chloroketimines has been studied. New types of ketones containing (O,O-diisopropyl phosphorothioyl)sulfanyl and (diphenylphosphinothioyl)sulfanyl groups were synthesized.

  DOI：

  10.1134/s1070363218100080
• 作为产物：
  描述：

  3-氯-3-甲基丁酮 、 异丙胺 在 四氯化钛 作用下， 以 苯 为溶剂， 反应 0.5h， 以91%的产率得到N-isopropyl-2-chloro-2-methyl-1-phenylpropan-1-imine
  参考文献：
  名称：

  Destabilized carbenium ions: α-imidoyl carbenium ions and the electron impact mass spectra of α-haloaldimines and α-haloketimines

  摘要：

  AbstractA series of α‐chloro‐ and α‐bromoketimines compounds (1‐9) with different substituents at the α‐position and at the imino group has been investigated by electron impact mass spectrometry as possible precursors of the correspondingly substituted α‐imidoyl carbenium ion, an important class of destabilized carbenium ions. The main fragmentation of the molecular ions of compounds, 1‐9 in the ion source corresponds to an α‐cleavage at the imino group; however, fragment ions are also formed by loss of the α‐halo substituent. These fragment ions correspond at least formally to α‐imidoyl carbenium ions. Their further reactions in dependence on the type of substituents at the imino group and at the α‐C atom, were studied by mass‐analysed ion kinetic energy and collisional activation mass spectrometry. The results agree with the initial formation of destabilized α‐imidoyl carbenium ions but indicate an easy rearrangement of these ions in the presence of suitable alkyl substituents by 1,2‐ and 1,4‐hydrogen shifts to more stable isomers.

  DOI：

  10.1002/oms.1210261014

文献信息

• Reactions of the N-isopropyl-α-chloroketimines with PIV dithioacids
  作者：M. B. Gazizov、R. A. Khairullin、Yu. S. Kirillina、S. Yu. Ivanova、Kh. R. Khayarov、O. D. Khairullina

  DOI：10.1007/s11172-018-2362-6

  日期：2018.12

  into products of nucleophilic substitution of the chlorine atom by dithiophosphorus group (SN pathway), if the imine carbon atom is bonded to the donor and small-volume methyl group, or undergoes reduction of the CCl bond (C-Cl→C-H) (Red pathway), when it is bonded with the bulky acceptor phenyl group. The same effect of substituents was discovered, when replacing methyl group with phenyl one in the

  在 PIV 二硫代酸与 N-异丙基-α-氯代酮亚胺反应中形成的伯亚胺盐转化为氯原子被二硫代磷基团亲核取代的产物（SN 途径），如果亚胺碳原子与供体键合并且较小-体积甲基，或当它与庞大的受体苯基键合时，会发生 CCl 键的还原（C-Cl→CH）（红色途径）。发现了同样的取代基作用，当用N-叔丁基-2-氯醛二亚胺的2位苯基1取代甲基时：SN：红色比在Me的情况下为1：0，在这种情况下为1：9 Ph. 亚胺盐被转化为含有磷官能团的新型酮。
• Destabilized carbenium ions: α-imidoyl carbenium ions and the electron impact mass spectra of α-haloaldimines and α-haloketimines
  作者：Thomas Sürig、Hans-Friedrich Grützmacher、Norbert de Kimpe

  DOI：10.1002/oms.1210261014

  日期：1991.10

  AbstractA series of α‐chloro‐ and α‐bromoketimines compounds (1‐9) with different substituents at the α‐position and at the imino group has been investigated by electron impact mass spectrometry as possible precursors of the correspondingly substituted α‐imidoyl carbenium ion, an important class of destabilized carbenium ions. The main fragmentation of the molecular ions of compounds, 1‐9 in the ion source corresponds to an α‐cleavage at the imino group; however, fragment ions are also formed by loss of the α‐halo substituent. These fragment ions correspond at least formally to α‐imidoyl carbenium ions. Their further reactions in dependence on the type of substituents at the imino group and at the α‐C atom, were studied by mass‐analysed ion kinetic energy and collisional activation mass spectrometry. The results agree with the initial formation of destabilized α‐imidoyl carbenium ions but indicate an easy rearrangement of these ions in the presence of suitable alkyl substituents by 1,2‐ and 1,4‐hydrogen shifts to more stable isomers.
• Reaction of P(IV) Dithio Acids with N-Alkyl-α-chloroketimines
  作者：R. A. Khairullin、M. B. Gazizov、Yu. S. Kirillina、Kh. R. Khayarov、S. Yu. Ivanova

  DOI：10.1134/s1070363218100080

  日期：2018.10

  Effect of the substituent on the imine carbon atom on the result of the reaction of P(IV) dithio acids with N-Alkyl--chloroketimines has been studied. New types of ketones containing (O,O-diisopropyl phosphorothioyl)sulfanyl and (diphenylphosphinothioyl)sulfanyl groups were synthesized.