cis-2,3-diphenyl-N-benzenesulphonylaziridine | 110143-77-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: cis-2,3-diphenyl-N-benzenesulphonylaziridine
• 英文别名: (2s,3r)-1-Benzenesulfonyl-2,3-diphenyl-aziridine；(2S,3R)-1-(benzenesulfonyl)-2,3-diphenylaziridine
• CAS: 110143-77-6
• 化学式: C₂₀H₁₇NO₂S
• 分子量: 335.426
• InChiKey: MAMOEUFINGBFJF-WCRBZPEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  9,10-二氢蒽 、 cis-2,3-diphenyl-N-benzenesulphonylaziridine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以84%的产率得到N-[2-(9,10-dihydroanthracen-9-yl)-1,2-diphenylethyl]benzenesulfonamide
  参考文献：
  名称：

  Mall; Stamm, Pharmazie, 1996, vol. 51, # 11, p. 831 - 833

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-2,3-diphenylaziridine 、 苯磺酰氯 以53%的产率得到
  参考文献：
  名称：

  MALL, THOMAS;STAMM, HELMUT, J. ORG. CHEM., 52,(1987) N 21, 4812-4814

  摘要：

  DOI：

文献信息

• Reaction of dimethyloxosulfonium methylide with N-arylsulfonylaziridines - stereospecific conversion of N-arylsulfonylaziridines to N-arylsulfonylazetidines
  作者：Upender K. Nadir、Raman L. Sharma、Veerinder K. Koul

  DOI：10.1016/s0040-4020(01)80051-x

  日期：1989.1

  Reaction of N-arylsulfonylaziridines with dimethyloxosulfonium methylide leads to the corresponding azetidines stereospecifically; the cis-aziridines yielding the trans-azetidines and the trans-aziridines furnishing the cis-azetidines. This stereochemical course is interpreted in terms of an SN2-1,4-elimination mechanism.

  N-芳基磺酰基氮丙啶与甲基二甲基氧ulf反应生成相应的氮杂环丁烷。产生反式氮杂环丁烷的顺式氮丙啶和提供顺式氮杂环丁烷的反式氮丙啶。该立体化学过程根据SN 2 -1，4-消除机理来解释。
• Enantioselective synthesis of aziridines from imines and alkyl halides using a camphor-derived chiral sulfide mediator via the imino Corey–Chaykovsky reaction
  作者：Takao Saito、Masao Sakairi、Daisuke Akiba

  DOI：10.1016/s0040-4039(01)01016-4

  日期：2001.8

  Asymmetric one-pot aziridination of imines with alkyl bromides via the imino Corey-Chaykovsky reaction mediated by chiral sulfide is described. The desired aziridines are obtained in good yields with up to 98% ee of the trans isomer. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Reactions with aziridines. 48. Friedel-Crafts reactions with N-sulfonated aziridines and with open-chain sulfonamides. Sulfonamides as leaving groups in open-chain structures
  作者：Helmut Stamm、Andreas Onistschenko、Berthold Buchholz、Thomas Mall

  DOI：10.1021/jo00262a042

  日期：1989.1
• Single electron transfer versus nucleophilic ring opening in reactions of cis-trans pairs of activated 2-phenylaziridines. Strong influence of nitrogen pyramid for N-benzoylaziridines
  作者：Reinhard Falkenstein、Thomas Mall、Dieter Speth、Helmut Stamm

  DOI：10.1021/jo00078a014

  日期：1993.12

  Activated 2-phenylaziridines with a second substituent R in position 3 were made to react with xanthyl anion X-. Nucleophilic ring opening ia the only reaction that occurs with sulfonyl activation. The analogous N-benzoylaziridines 1 undergo this type of ring opening when the two substituents Ph and R are trans. The cis isomers (cis-1, Ph and R cis) react in this manner to a negligible extent if any. The (nearly) exclusive ring cleavage reaction of cis-1 is C-N homolysis of an intermediate ketyl formed by single electron transfer (SET) from X-. This cis-trans phenomenon is in accordance with the hypothesis that the two competing reactions depend in an opposite manner on the steepness of the nitrogen pyramid. A predominant or exclusive final result of SET is reductive aziridine opening and dimerization of the xanthyl radical X.. Formation of both diastereomers of the[GRAPHICS]amidoethylated xanthene in one case (R = Me) is evidence for a cross combination of X. with the radical formed by homolytic ring opening. Cross combination is also a likely path for R = H (no cis-trans isomerism), in addition to reductive ring opening. cis-Aziridines with dimethylcarbamoyl on nitrogen do not react via SET since the ketyl is not stabilized and therefore difficult to generate. Carbonyl attack on both types of acylaziridines competes more or less successfully with the two ring cleavage reactions.
• Reactions with aziridines. 43. Reactivity difference of cis-trans pairs: different behavior of stilbene oxides and activated stilbene imines
  作者：Thomas Mall、Helmut Stamm

  DOI：10.1021/jo00230a035

  日期：1987.10