1-((4-bromophenyl)sulfonyl)-2-phenylaziridine

• 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: 1-((4-bromophenyl)sulfonyl)-2-phenylaziridine
• 英文别名: 1-(4-Bromophenyl)sulfonyl-2-phenylaziridine
• 化学式: C₁₄H₁₂BrNO₂S
• 分子量: 338.225
• InChiKey: PLYKXRHJAGDMME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：

  1-((4-bromophenyl)sulfonyl)-2-phenylaziridine 在 2-甲基喹啉 、 二甲基亚砜 作用下， 以82%的产率得到4-bromo-N-(2-oxo-2-phenylethyl)benzenesulfonamide
  参考文献：
  名称：

  2-甲基喹啉通过DMSO促进N-磺酰基氮丙啶的氧化开环：轻松合成α-氨基芳基酮

  摘要：

  已经开发了2-甲基喹啉用DMSO促进N-磺酰基氮丙啶的室温氧化开环，为合成各种不同的N-磺酰基保护的α-氨基芳基酮提供了一种温和而便捷的方法。2-甲基喹啉的使用对于这种温和转化的成功至关重要，并且可以实现良好的优良收率。

  DOI：

  10.1016/j.tet.2016.10.041

文献信息

• Et3N-promoted tandem ring-opening reaction of N-tosylaziridines with terminal alkynoates: a straightforward synthesis of functionalized enamines
  作者：Ling-Guo Meng、Lei Wang

  DOI：10.1039/c2cc30317e

  日期：——

  A tandem ring-opening reaction of N-tosylaziridines with terminal alkynoates promoted by Et3N has been described. A variety of N-tosylaziridines reacted with terminal alkynoates to give functionalized enamines in moderate to good yields under simple reaction conditions.

  已经描述了一种由三乙胺催化的N-托磺酰亚胺与末端炔酸酯的串联开环反应。多种N-托磺酰亚胺与末端炔酸酯反应，在简单的反应条件下得到功能化的烯胺，产率中等至良好。
• An Improved Protocol for Regioselective Ring-Opening of Sulfonyl Aziridines with Iodine Promoted by PPh₃
  作者：Jinfeng Zhang、Lingguo Meng、Chuntao Li、Guoyuan Xiao

  DOI：10.1002/cjoc.201300625

  日期：2013.12

  A new route to synthesize β‐iodo amines from sulfonyl aziridines and iodine was developed in the presence of PPh3. This ring‐opening reaction was an efficient and simple process to give β‐iodo amines in excellent yields with high chemoselectivity.

  在PPh 3存在下，开发了一种从磺酰基氮丙啶和碘合成β-碘胺的新途径。这种开环反应是一种高效简单的方法，可以以高收率和高化学选择性得到β-碘胺。
• Palladium(II)-Catalyzed Formal [3 + 2] Cycloaddition of Aziridines with 3-Substituted Indoles: Synthesis of Enantioenriched Pyrroloindolines
  作者：You-ming Huang、Chang-wu Zheng、Lu Pan、Qiao-wen Jin、Gang Zhao

  DOI：10.1021/acs.joc.5b01931

  日期：2015.11.6

  A Pd-catalyzed enantiospecific formal [3 + 2] cycloaddition between chiral aziridines and indoles has been developed. With this method, chiral pyrroloindolines in enantiomerically pure forms were constructed in high yields and diastereoselectivities under mild conditions.
• DABCO-Promoted Unexpected Regioselective Ring Opening and Stereoselective Addition Reactions of Sulfonylaziridines with Cyanoacetylenes: Access to Functionalized Enenitriles
  作者：Ling-Guo Meng、Lei Wang

  DOI：10.1002/adsc.201300454

  日期：2013.10.11

  AbstractA highly regioselective ring opening and stereoselective addition reaction of sulfonylaziridines with cyanoacetylenes promoted by 1,4‐diazabicyclo[2.2.2]octane (DABCO) was investigated. A variety of functionalized (Z)‐enenitriles could be obtained in good yields through regioselective cleavage of carbon‐nitrogen bonds in sulfonylaziridines.magnified image
• Lewis acid promoted three-component reactions of aziridines, arenes and aldehydes: an efficient and diastereoselective synthesis of cis-1,4-disubstituted tetrahydroisoquinolines
  作者：Siyang Xing、Jing Ren、Kui Wang、Hong Cui、Wenrui Li、Han Yan

  DOI：10.1016/j.tet.2015.06.013

  日期：2015.9

  A new Lewis acid promoted three-component reaction between the aziridine, arene and aldehyde has been developed. This reaction involves sequential ring opening of aziridine and Pictet-Spengler condensation and gives a broad range of cis-1,4-disubstituted tetrahydroisoquinolines in moderate yields with good diastereoselectivities under mild conditions. The methodology provides a rapid and convergent synthesis for the scaffold of tetrahydroisoquinoline and serves as a good tool for constructing the libraries of substituted tetrahydroisoquinolines. (C) 2015 Elsevier Ltd. All rights reserved.