cis-2-Benzoyl-3-(4-chlorophenyl)-1-tosylaziridine

• 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: cis-2-Benzoyl-3-(4-chlorophenyl)-1-tosylaziridine
• 英文别名: 2-benzoyl-3-(p-chlorophenyl)-1-tosylaziridine；((2R*,3R*)-3-(4-chlorophenyl)-1-tosylaziridin-2-yl)(phenyl)methanone；[(2S,3S)-3-(4-chlorophenyl)-1-(4-methylphenyl)sulfonylaziridin-2-yl]-phenylmethanone
• 化学式: C₂₂H₁₈ClNO₃S
• 分子量: 411.909
• InChiKey: MJFBZIXFEDRKRA-GAIPOIILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到cis-2-Benzoyl-3-(4-chlorophenyl)-1-tosylaziridine
  参考文献：
  名称：

  A Three Component Protocol for the Synthesis of Aziridines using BF3·(OEt)2

  摘要：

  使用苯乙酰溴、对甲苯磺酰胺和羧醛在二氯甲烷中以BF3·(OEt)2等温和路易斯酸的存在下进行三组分反应，合成了N-(1R,2S)-2-(溴代-3-氧代-1,3-二苯基丙基)-4-甲基苯磺酰胺和N-(1R,2S)-(2-溴代-3-氧代-1,3-二苯基丙基)-4-甲基苯磺酰胺。该合成方法可用于合成相应的顺式环丙烷，对于多种取代羧醛和取代苯乙酰溴都表现出操作简便的合成效果。

  DOI：

  10.14233/ajchem.2020.22315

文献信息

• Scope and limitations of diastereoselective aziridination reactions using stabilised ammonium ylides or α-bromo carbonyl nucleophiles
  作者：Stefan Aichhorn、Guddeangadi N. Gururaja、Michael Reisinger、Mario Waser

  DOI：10.1039/c3ra40429c

  日期：——

  The applicability of easily available ammonium salts to access aziridines via an ammonium ylide pathway was carefully investigated and compared with classical aza-Darzens approaches using α-bromo carbonyl nucleophiles. Whereas amide-stabilised ammonium ylides could be successfully reacted with aromatic aldimines to obtain the corresponding trans-aziridines in good yields and with high diastereoselectivities, α-bromo amides failed. In sharp contrast, acetophenone-based ylides did not give any aziridines while in this specific case α-bromo acetophenone derivatives gave the corresponding cis-aziridines in high yields and with excellent diastereoselectivities under optimised conditions.

  我们仔细研究了易于获得的铵盐通过醯化铵途径获得氮丙啶的适用性，并将其与使用δ-溴羰基亲核体的经典氮杂-达臻方法进行了比较。酰胺稳定的醯化铵可成功地与芳香族醛亚胺反应，以良好的产率和高非对映选择性获得相应的反式氮丙啶，而δ-溴酰胺则失败了。与此形成鲜明对比的是，苯乙酮基酰化物没有得到任何氮丙啶，而在这种特定情况下，δ-溴苯乙酮衍生物在优化条件下以高产率和极好的非对映选择性得到了相应的顺式氮丙啶。
• Michael-type addition of hydroxide to alkynylselenonium salt: practical use as a ketoselenonium ylide precursor
  作者：Shin-ichi Watanabe、Shinsuke Asaka、Tadashi Kataoka

  DOI：10.1016/j.tetlet.2004.08.036

  日期：2004.9

  A novel synthetic method of ketodiphenylselenonium ylide from alkynylselenonium salt is described. A reaction of alkynylselenonium salt, hydroxide ion, and aldehyde in the presence of silver triflate and triethylamine gave oxiranylketones just as a trans-isomer in moderate to good yields, whereas benzoyl aziridine derivatives were obtained from the reaction with sodium p-toluenesulfonamide instead

  描述了一种从炔基硒鎓盐合成酮二苯基硒鎓叶立德的新方法。在三氟甲磺酸银和三乙胺的存在下，炔基硒鎓盐，氢氧根离子和醛的反应以中等至良好的收率得到了环氧乙烷基酮，就像反式异构体一样，而苯甲酰基氮丙啶衍生物是从与对甲苯磺酰胺钠而不是苯甲酰胺的反应中获得的。氢氧根离子
• 3-Substituted 2-Acyl-1-sulfonylaziridines from the Reaction of Triphenylbismuthonium 2-Oxoalkylides and N-Sulfonylaldimines. Reversal of the cis/trans-Isomer Ratios Depending on Base and Additive
  作者：Yoshihiro Matano、Masanori Yoshimune、Hitomi Suzuki

  DOI：10.1021/jo00119a056

  日期：1995.7
• A Three Component Protocol for the Synthesis of Aziridines using BF3·(OEt)2
  作者：Shaik Firoj Basha、Shaik Anwar

  DOI：10.14233/ajchem.2020.22315

  日期：——

  Synthesis of N-(1R,2S)-2-(bromo-3-oxo-1,3-diphenylpropyl)-4-methylbenzene sulfonamide and N-(1R,2S)-(2-bromo-3-oxo-1,3-diphenylpropyl)-4-methylbenzene sulfonamide was carried out by a three component reaction using phenacyl bromide, p-toluenesulfonamide and carboxyaldehyde in presence of mild Lewis acid such as BF3·(OEt)2 in dichloromethane. The synthetic utility of this protocol was carried out with syn-isomer to yield corresponding cis-aziridines. This protocol was operationally simple for a wide variety of substituted carboxaldehydes and substituted phenacyl bromides.

  使用苯乙酰溴、对甲苯磺酰胺和羧醛在二氯甲烷中以BF3·(OEt)2等温和路易斯酸的存在下进行三组分反应，合成了N-(1R,2S)-2-(溴代-3-氧代-1,3-二苯基丙基)-4-甲基苯磺酰胺和N-(1R,2S)-(2-溴代-3-氧代-1,3-二苯基丙基)-4-甲基苯磺酰胺。该合成方法可用于合成相应的顺式环丙烷，对于多种取代羧醛和取代苯乙酰溴都表现出操作简便的合成效果。