cis-2-methyl-1-(4-methylphenylsulfonyl)-3-pentylaziridine

• 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-methyl-1-(4-methylphenylsulfonyl)-3-pentylaziridine
• 英文别名: cis-N-(p-toluenesulfonyl)-2-methyl-3-n-pentylaziridine；cis-N-(p-toluenesulfonyl)-2-methyl-3-pentylaziridine；(2S,3R)-2-methyl-1-(4-methylphenyl)sulfonyl-3-pentylaziridine
• 化学式: C₁₅H₂₃NO₂S
• 分子量: 281.419
• InChiKey: VYQZFSBPTGGDFZ-GVJPCGBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  cis-2-methyl-1-(4-methylphenylsulfonyl)-3-pentylaziridine 在 正丁基锂 、 potassium tert-butylate 、 二异丙胺 作用下， 以 正己烷 、 正戊烷 为溶剂， 以40%的产率得到4-methyl-N-[(E)-oct-3-en-2-yl]benzenesulfonamide
  参考文献：
  名称：

  Base-promoted elaboration of aziridines

  摘要：

  The base-promoted isomerization of aziridines to allyl amines is still an almost unknown reaction. However, the use of superbasic reagents has shown to be able to promote a regio- and stereoselective conversion of monocyclic and bicyclic sulfonyl aziridines. Moreover, the use of alkoxy substituted aziridines opens new routes to non-natural alpha- and beta-amino acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00729-9
• 作为产物：
  描述：

  顺-2-辛烯 、 chloroamine-T 在 碘 作用下， 以 乙腈 为溶剂， 生成 cis-2-methyl-1-(4-methylphenylsulfonyl)-3-pentylaziridine
  参考文献：
  名称：

  Lewis碱与甲硅烷基化的亲核试剂催化氮丙啶的开环。

  摘要：

  N，N，N′，N′-四甲基乙二胺催化的N-甲苯磺酰氮丙啶与三甲基甲硅烷基化的亲核试剂的开环导致β-官能化磺酰胺的生产，具有良好的产率和高的区域选择性。[反应：看文字]

  DOI：

  10.1021/ol051186f

文献信息

• Novel aziridination of olefins: direct synthesis from sulfonamides using t-BuOI
  作者：Satoshi Minakata、Yoshinobu Morino、Yoji Oderaotoshi、Mitsuo Komatsu

  DOI：10.1039/b606499j

  日期：——

  (t-BuOI) was found to be a powerful reagent for synthesis of aziridines from olefins and sulfonamides. The aziridination of olefins was achieved by using sulfonamides with t-BuOI. Our preliminary findings represent the example of metal-free aziridination of olefins with readily accessible sulfonamides as a nitrogen source.

  叔丁基次碘酸盐（t-BuOI）被发现是从烯烃和磺酰胺合成氮丙啶的有力试剂。通过使用磺酰胺与t-BuOI来实现烯烃的叠氮化。我们的初步发现代表了使用易于获得的磺酰胺作为氮源的烯烃无金属叠氮化的示例。
• Novel organic-solvent-free aziridination of olefins: Chloramine-T–I2 system under phase-transfer catalysis conditions
  作者：Daisuke Kano、Satoshi Minakata、Mitsuo Komatsu

  DOI：10.1039/b104940m

  日期：2001.11.29

  A variety of olefins could be aziridinated successfully by employing iodine-catalysed aziridination in water with a catalytic amount of a quaternary ammonium salt. Furthermore, the larger-scale process of styrene aziridination gives a highly pure aziridine in good yield via simple work-up.

  通过在水中使用催化量的季铵盐进行碘催化的氮丙啶化，可以成功地对多种烯烃进行氮丙啶化。此外，大规模的苯乙烯氮丙啶化过程可以通过简单的后处理以良好的收率得到高纯度的氮丙啶。
• Silica–Water Reaction Media: Its Application to the Formation and Ring Opening of Aziridines
  作者：Satoshi Minakata、Daisuke Kano、Yoji Oderaotoshi、Mitsuo Komatsu

  DOI：10.1002/anie.200352842

  日期：2004.1
• Iodine-catalyzed aziridination of alkenes using Chloramine-T as a nitrogen source
  作者：Takeya Ando、Daisuke Kano、Satoshi Minakata、Ilhyong Ryu、Mitsuo Komatsu

  DOI：10.1016/s0040-4020(98)00827-8

  日期：1998.10

  Iodine was found to be an efficient catalyst for the aziridination of alkenes utilizing Chloramine-T (N-chloro-N-sodio-p-toluenesulfonamide) as a nitrogen source. For example, when two equivalents of styrene were added to Chloramine-T in the presence of a catalytic amount of iodine in a 1 : 1 solvent mixture of acetonitrile and neutral buffer, the corresponding aziridine 1 was obtained in 91% yield. The reaction could be applied to other acyclic and cyclic alkenes such as 1-octene and cyclohexene. The aziridination of p-substituted styrene derivatives 2-5 with Chloramine-T showed that electron-rich alkenes reacted faster than electron-poor ones. Several Chloramine-T analogs were also examined and were found to give the corresponding aziridines 8-10 in only moderate yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Minakata, Satoshi; Kano, Daisuke; Fukuoka, Ryoko, Heterocycles, 2003, vol. 60, # 2, p. 289 - 298
  作者：Minakata, Satoshi、Kano, Daisuke、Fukuoka, Ryoko、Oderaotoshi, Yoji、Komatsu, Mitsuo

  DOI：——

  日期：——