N-(4-methoxybenzenesulfonyl)-(2S)-benzylaziridine | 219738-94-0

• 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-methoxybenzenesulfonyl)-(2S)-benzylaziridine
• 英文别名: (S)-2-Benzyl-1-(4-methoxybenzenesulfonyl)aziridine；(2S)-2-benzyl-1-(4-methoxyphenyl)sulfonylaziridine
• CAS: 219738-94-0
• 化学式: C₁₆H₁₇NO₃S
• 分子量: 303.382
• InChiKey: CKSBMYLGURDCEW-MBIQTGHCSA-N

物化性质

• 熔点：
  94-95 °C(Solv: pentane (109-66-0); ethyl acetate (141-78-6))
• 沸点：
  456.5±47.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzenesulfonyl)-(2S)-benzylaziridine 在 N,N-二甲基丙烯基脲 、 samarium (III) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以55%的产率得到N-<2-(1-iodo-3-phenylpropyl)>-4-methoxyphenylsulfonamide
  参考文献：
  名称：

  Deprotection of Sulfonyl Aziridines

  摘要：

  The deprotection of the chiral N-sulfonyl aziridines 1-3 has been studied under different desulfonylation conditions. Two methods for the efficient deprotection of 2-benzyl-, 2-phenyl-, and 2-carboxyl-N-sulfonylaziridines were found. The desulfonylation with lithium and a catalytic amount of di-tert-butyl biphenyl in THF at -78 degrees C led to the corresponding NH aziridines with yields up to 85%. Alternatively, the desulfonylation could be carried out with magnesium in methanol under ultrasonic conditions. The latter proved to be avery mild method and afforded the desulfonylated aziridines with yields up to 75%, even when the 2-phenyl substituted aziridine 2 was the studied substrate. Furthermore, in all the cases studied, no racemization was observed in the chiral center of the aziridines.

  DOI：

  10.1021/jo9815296
• 作为产物：
  描述：

  N-((S)-1-Hydroxymethyl-2-phenyl-ethyl)-4-methoxy-benzenesulfonamide 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-(4-methoxybenzenesulfonyl)-(2S)-benzylaziridine
  参考文献：
  名称：

  Deprotection of Sulfonyl Aziridines

  摘要：

  The deprotection of the chiral N-sulfonyl aziridines 1-3 has been studied under different desulfonylation conditions. Two methods for the efficient deprotection of 2-benzyl-, 2-phenyl-, and 2-carboxyl-N-sulfonylaziridines were found. The desulfonylation with lithium and a catalytic amount of di-tert-butyl biphenyl in THF at -78 degrees C led to the corresponding NH aziridines with yields up to 85%. Alternatively, the desulfonylation could be carried out with magnesium in methanol under ultrasonic conditions. The latter proved to be avery mild method and afforded the desulfonylated aziridines with yields up to 75%, even when the 2-phenyl substituted aziridine 2 was the studied substrate. Furthermore, in all the cases studied, no racemization was observed in the chiral center of the aziridines.

  DOI：

  10.1021/jo9815296

文献信息

• Large scale synthesis of optically pure aziridines
  申请人：——

  公开号：US20030153771A1

  公开（公告）日：2003-08-14

  Disclosed is an efficient, inexpensive method for the preparation of chiral aziridines on a large scale.

  公开了一种高效、廉价的大规模制备手性环氧乙烷的方法。
• Diastereoselective Pyrrolidine Synthesis via Copper Promoted Intramolecular Aminooxygenation of Alkenes: Formal Synthesis of (+)-Monomorine
  作者：Monissa C. Paderes、Sherry R. Chemler

  DOI：10.1021/ol9003492

  日期：2009.5.7

  substrate whose N-substituent was directly tethered to the α-carbon exclusively yielded the 2,5-trans pyrrolidine. The synthetic utility of the method was demonstrated by a short and efficient formal synthesis of (+)-monomorine.

  研究了铜促进的各种烯烃底物分子内氨基氧化的非对映选择性。α-取代的 4-戊烯基磺酰胺有利于形成 2,5-顺式吡咯烷 (dr >20:1)，产率极好，范围为 76−97%，而 γ-取代的底物则有利于 2,3-反式吡咯烷加合物中等选择性（约 3:1）。N-取代基直接连接到 α-碳的底物仅产生 2,5-反式吡咯烷。该方法的合成实用性通过 (+)-monomorine 的简短有效的形式合成得到了证明。
• One-pot and microwave-assisted synthesis of N-sulfonylaziridines
  作者：Hao Xu、Hua Tian、Liangyu Zheng、Qingwen Liu、Li Wang、Suoqin Zhang

  DOI：10.1016/j.tetlet.2011.03.106

  日期：2011.6

  A novel and efficient microwave-assisted one-step reaction was developed to synthesize chiral N-sulfonylaziridines by the reaction of different chiral amino alcohols and sulfonic chlorides. The newly developed microwave synthetic method has the advantage of reducing the reaction time from 24 to 0.5 h with improved yields (84-93%) and minimizing by-products. (C) 2011 Elsevier Ltd. All rights reserved.