吖丙啶,2-(4-氯苯基)-1-(苯磺酰)- | 137152-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 吖丙啶,2-(4-氯苯基)-1-(苯磺酰)-
• 英文名称: 2-(4-chlorophenyl)-1-phenylsulfonylaziridine
• 英文别名: 1-(Benzenesulfonyl)-2-(4-chlorophenyl)aziridine
• CAS: 137152-08-0
• 化学式: C₁₄H₁₂ClNO₂S
• 分子量: 293.774
• InChiKey: CHKCWQRJGRKEMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  444.9±55.0 °C(Predicted)
• 密度：
  1.414±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (dimethylsulfuranylidene)acetate 、 吖丙啶,2-(4-氯苯基)-1-(苯磺酰)- 以 N,N-二甲基甲酰胺 为溶剂， 以39%的产率得到cis-ethyl 4-(p-chlorophenyl)-1-phenylsulfonylazetidine-2-carboxylate
  参考文献：
  名称：

  Reaction of N-arylsulfonylaziridines with dimethylsulfoniumethoxycarbonyl methylide: regio- and stereo-selective synthesis of 1-arylsulfonyl-2-ethoxycarbonyl azetidines

  摘要：

  Synthesis and characterization of 4-aryl-, 3,4-diaryl- and 3-alkyl-4-aryl-N-arylsulfonylazetidines, bearing a 2-ethoxycarbonyl group are described. The methodology used involves transfer of an ethoxycarbonyl substituted methylene group from dimethylsulfoniumethoxycarbonyl methylide to N-arylsulfonylaziridines. The synthesis is both regio- and stereo-selective.

  DOI：

  10.1039/p19950002605
• 作为产物：
  描述：

  4-氯苯乙烯 在 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 吖丙啶,2-(4-氯苯基)-1-(苯磺酰)-
  参考文献：
  名称：

  A Convenient Method for the Synthesis of 2-Arylaziridines from Styrene Derivatives via 2-Arylethenyl(diphenyl)sulfonium Salts

  摘要：

  苯乙烯衍生物在低温下与二苯基（三氟甲磺酰氧基）锍三氟甲磺酸盐（1）反应，生成2-芳基乙烯基（二苯基）锍三氟甲磺酸盐（2）。将2与一级胺反应，可高产率地得到相应的2-芳基氮杂环丙烷。多种氮杂环丙烷的一锅法合成也成功实现，无需分离中间体2。

  DOI：

  10.1246/cl.2003.392

文献信息

• Nadir, Upender K.; Sharma, Ms. Raman L.; Koul, Veerinder K., Journal of the Chemical Society. Perkin transactions I, 1991, # 8, p. 2015 - 2020
  作者：Nadir, Upender K.、Sharma, Ms. Raman L.、Koul, Veerinder K.

  DOI：——

  日期：——
• Addition Reactions of Chloro- or Iodomethyllithium to Imines. Synthesis of Enantiopure Aziridines and β-Chloroamines
  作者：José M. Concellón、Humberto Rodríguez-Solla、Pablo L. Bernad、Carmen Simal

  DOI：10.1021/jo802596y

  日期：2009.3.20

  We report a novel, simple, and efficient synthesis of aziridines and 1-chloroalkan-2-amines by the reaction of imines derived from various aldehydes and p-toluenesulfonamide or benzenesulfonamide with iodoor chloromethyllithium, respectively. Both halogenated anions were generated in situ by treatment of diiodo- or chloroiodomethane with methyllithium at -78 or 0 degrees C. The reaction of in situ generated iodo- or chloromethyllithium could also be performed from chiral 2-aminoaldimines to yield enantiopure aziridines or (2S,3S)-2,3-diamino-1-chloroalkanes with high stereoselectivity.
• Nadir, Upender K.; Arora, Anjali, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 2, p. 297 - 298
  作者：Nadir, Upender K.、Arora, Anjali

  DOI：——

  日期：——
• Nadir, Upender K.; Arora, Anjali, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 2, p. 163 - 166
  作者：Nadir, Upender K.、Arora, Anjali

  DOI：——

  日期：——
• A Convenient Method for the Synthesis of 2-Arylaziridines from Styrene Derivatives via 2-Arylethenyl(diphenyl)sulfonium Salts
  作者：Jun-ichi Matsuo、Hiroyuki Yamanaka、Asahi Kawana、Teruaki Mukaiyama

  DOI：10.1246/cl.2003.392

  日期：2003.4

  Styrene derivatives reacted with diphenyl(trifluoromethanesulfonyloxy)sulfonium trifluoromethanesulfonate (1) at low temperature to afford 2-arylethenyl(diphenyl)sulfonium triflates (2). Treatment of 2 with primary amines gave the corresponding 2-arylaziridines in high yields. One-pot synthesis of various aziridines was also successfully carried out without isolation of the intermediate 2.

  苯乙烯衍生物在低温下与二苯基（三氟甲磺酰氧基）锍三氟甲磺酸盐（1）反应，生成2-芳基乙烯基（二苯基）锍三氟甲磺酸盐（2）。将2与一级胺反应，可高产率地得到相应的2-芳基氮杂环丙烷。多种氮杂环丙烷的一锅法合成也成功实现，无需分离中间体2。