N-(4-methoxyphenyl)-1-[(R)-(4-methylphenyl)sulfinyl]pentan-2-imine | 260560-97-2

• 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-(4-methoxyphenyl)-1-[(R)-(4-methylphenyl)sulfinyl]pentan-2-imine
• CAS: 260560-97-2
• 化学式: C₁₉H₂₃NO₂S
• 分子量: 329.463
• InChiKey: OSXJSJIWXZYQLJ-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-1-[(R)-(4-methylphenyl)sulfinyl]pentan-2-imine 在 二异丁基氢化铝 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,(S)R)-N-(p-methoxyphenyl)-1-n-propyl-2-(p-tolylsulfinyl)ethylamine
  参考文献：
  名称：

  来自2-亚磺酰亚胺的对映体纯的2-烷基和2,3-二烷基氮丙啶

  摘要：

  一个新的项，以从光学纯氮丙啶Np个2-甲氧基苯基衍生物p报道-tolylsulfinylketimines。用DIBAL-H / ZnX 2对亚胺进行高度立体选择性还原，生成了相应的亚磺酰基胺，可以通过两步序列将其转化为N -Cbz衍生物，该过程涉及与BnO 2 CCl反应并随后与CAN氧化。通过还原亚磺酰基，在硫上进一步甲基化以及用碱进行最终环化，可以轻松地将这些化合物转化为光学上纯的氮丙啶。

  DOI：

  10.1016/s0040-4039(98)02168-6
• 作为产物：
  描述：

  甲氧苯胺 、 (+)-(R)-1-(p-tolylsulfinyl)-2-pentanone 在 3 A molecular sieve 作用下， 以 苯 为溶剂， 反应 48.0h， 以60%的产率得到N-(4-methoxyphenyl)-1-[(R)-(4-methylphenyl)sulfinyl]pentan-2-imine
  参考文献：
  名称：

  Synthesis of enantiomerically pure acyclic α-sulfinyl ketimines

  摘要：

  Two different methods to obtain enantiomerically pure N-alkyl and N-aryl alpha-sulfinyl ketimines are reported. Reaction of enantiomerically pure alpha-sulfinyl ketones (1-6) with benzylamine or p-methoxyaniline, in the presence of molecular sieves (3 Angstrom), yields the corresponding of N-benzyl and N-p-methoxyphenyl ketimines (7A-12A and 7B-12B). Better results were achieved by alpha-sulfinylation of ketimines (13A-18A and 13B-18B) with (-)-menthyl p-toluenesulfinate in the presence of lithium (N-arylimines) or magnesium (N-benzylimines) bases. The different tautomeric behaviour of the obtained N-aryl and N-alkyl derivatives is reported. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00211-0

文献信息

• Synthesis of enantiomerically pure acyclic α-sulfinyl ketimines
  作者：José L Garcı́a Ruano、Antonio Lorente、Jesús H Rodrı́guez Ramos

  DOI：10.1016/s0957-4166(98)00211-0

  日期：1998.7

  Two different methods to obtain enantiomerically pure N-alkyl and N-aryl alpha-sulfinyl ketimines are reported. Reaction of enantiomerically pure alpha-sulfinyl ketones (1-6) with benzylamine or p-methoxyaniline, in the presence of molecular sieves (3 Angstrom), yields the corresponding of N-benzyl and N-p-methoxyphenyl ketimines (7A-12A and 7B-12B). Better results were achieved by alpha-sulfinylation of ketimines (13A-18A and 13B-18B) with (-)-menthyl p-toluenesulfinate in the presence of lithium (N-arylimines) or magnesium (N-benzylimines) bases. The different tautomeric behaviour of the obtained N-aryl and N-alkyl derivatives is reported. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Enantiomerically pure 2-alkyl and 2,3-dialkylaziridines from 2-sulfinylimines
  作者：JoséL. García Ruano、Antonio Lorente、Jesús H. Rodríguez Ramos

  DOI：10.1016/s0040-4039(98)02168-6

  日期：1998.12

  A new entry to optically pure aziridines from N-p-methoxyphenyl derivatives of 2-p-tolylsulfinylketimines is reported. The highly stereoselective reduction of the imines with DIBAL-H/ZnX2 yielded the corresponding sulfinyl amines, which can be transformed into the N-Cbz derivatives through a two-step sequence involving reaction with BnO2CCl and subsequent oxidation with CAN. These compounds were easily

  一个新的项，以从光学纯氮丙啶Np个2-甲氧基苯基衍生物p报道-tolylsulfinylketimines。用DIBAL-H / ZnX 2对亚胺进行高度立体选择性还原，生成了相应的亚磺酰基胺，可以通过两步序列将其转化为N -Cbz衍生物，该过程涉及与BnO 2 CCl反应并随后与CAN氧化。通过还原亚磺酰基，在硫上进一步甲基化以及用碱进行最终环化，可以轻松地将这些化合物转化为光学上纯的氮丙啶。