2-Hexadecyl-1-(toluene-4-sulfonyl)-aziridine | 502697-25-8

• 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: 2-Hexadecyl-1-(toluene-4-sulfonyl)-aziridine
• 英文别名: 2-Hexadecyl-1-(4-methylphenyl)sulfonylaziridine
• CAS: 502697-25-8
• 化学式: C₂₅H₄₃NO₂S
• 分子量: 421.688
• InChiKey: IEQCESBRDQNNEA-UHFFFAOYSA-N

物化性质

• 沸点：
  522.4±43.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  2-Hexadecyl-1-(toluene-4-sulfonyl)-aziridine 在 nickel(II) chloride hexahydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以99%的产率得到N-(1-chlorooctadecan-2-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Hydrated nickel (II) halides mediated ring opening reaction with N-tosylaziridines

  摘要：

  An efficient and water tolerant method for the synthesis of beta-haloamines is described utilizing hydrated nickel (II) halides (NiX2 center dot nH(2)O X = Cl, Br, I) and aziridines as starting materials. N-Tosylaziridines reacted with NiCl2 center dot 6H(2)O or NiI2 center dot 6H(2)O giving beta-chloro- or beta-iodoamines in high yields (73-99%) within a short time, but 10 mol% of n-Bu4NBr should be added in the reactions of N-tosylaziridines with NiBr2 center dot 3H(2)O in order to obtain the high yields of corresponding beta-bromoamines. Solvent played an important role in the reactions. The proper solvent for the reaction of NiCl2 center dot 6H(2)O was DMF, while NiBr2 center dot 3H(2)O or NiI2 center dot 6H(2)O proceeded well in 1,4-dioxane. (C) 2011 Wan Xuan Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.12.005
• 作为产物：
  描述：

  十八碳烯 、 对甲苯磺酰胺 在 4A MS 碘苯二乙酸 、 potassium tert-butylate 、 碘 作用下， 以 1,2-二氯乙烷 为溶剂， 以62%的产率得到2-Hexadecyl-1-(toluene-4-sulfonyl)-aziridine
  参考文献：
  名称：

  PhI(OAc)2/I2 induced aziridination of alkenes with TsNH2 under mild conditions

  摘要：

  The aziridination of alkenes with the direct use of p-toluenesulfonamide (TsNH2) was achieved by using PhI(OAc)(2) and I-2 under mild conditions. The reaction affords aziridines in moderate to good yields, and offers good manipulability by avoiding the use of the expensive metal catalyst and the unstable and explosive PhI=NTs. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.143

文献信息

• Cationic Micelle-catalyzed Ring-Opening Reactions of Aziridines with Thiols in Water
  作者：Min Yang、Qin Yang、Puqing Chen、Yiyuan Peng

  DOI：10.1002/cjoc.201190112

  日期：2011.3

  An efficient and practical method is described for the ring‐opening reactions of N‐tosylaziridines with various thiols in water under mild conditions. Various surfactants have been evaluated to optimize the reactions. Under optimal conditions, these reactions gave rise to the corresponding β‐amino sulfides in good to excellent yields.

  描述了一种在水中温和条件下N-甲苯磺酰基氮丙啶与各种硫醇的开环反应的有效而实用的方法。已经评估了各种表面活性剂以优化反应。在最佳条件下，这些反应以良好至极好的收率产生了相应的β-氨基硫化物。
• Pyridine-N-oxide: An Efficient Organocatalyst for Ring-Opening Reactions of Aziridines with Aryl Thiols
  作者：Qin Yang、Zhenlan Yin、Min Yang、Yiyuan Peng

  DOI：10.1002/cjoc.201190064

  日期：2011.1

  Pyridine‐N‐oxide serves as an efficient catalyst for the ring‐opening reactions of N‐tosylaziridines with various aryl thiols under mild conditions. This transformation is highly effective, which gives rise to the corresponding β‐amino sulfides in good to excellent yields.

  吡啶-N-氧化物是N-甲苯磺酰氮丙啶与各种芳基硫醇在温和条件下的开环反应的有效催化剂。这种转化是非常有效的，它以良好至极好的收率产生了相应的β-氨基硫化物。
• DABCO: An Efficient Organocatalyst in the Ring-Opening Reactions of Aziridines with Amines or Thiols
  作者：Jie Wu、Xiaoyu Sun、Yizhe Li

  DOI：10.1002/ejoc.200500576

  日期：2005.10

  Efficient ring-opening of aziridines with various amines or thiols catalyzed by DABCO afforded the corresponding products in good to excellent yields under mild reaction conditions. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  在 DABCO 的催化下，氮丙啶与各种胺或硫醇的有效开环在温和的反应条件下以良好到极好的收率提供了相应的产物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Direct Synthesis of Nitrones via Transition-Metal-Free Ring-Opening of N-Tosylaziridines with the Nitrogen Atom of Various (E)-Aldoximes and (E)-Ketoximes
  作者：Xing Li、Wenjing Yan、Rui Zhang、Honghong Chang、Wenchao Gao、Xiuping Tian、Wenlong Wei

  DOI：10.1055/s-0039-1690186

  日期：2019.11

  The KOH-, K2CO3-, or Et3N-catalyzed ring-opening reaction of N-tosylaziridines using the nitrogen atom of a series of (E)-aldoximes and (E)-ketoximes as a nucleophilic atom instead of an oxygen atom was developed to construct various nitrones under mild reaction conditions. Diverse (E)-aldoximes and (E)-ketoximes were demonstrated to be compatible with this reaction and the products of O-ring-opening reactions were not detected for most examples.

  KOH-、K2CO3-或Et3N催化的N-对甲苯磺酰基环氧丙烷的开环反应，使用(E)-醛肟和(E)-酮肟系列化合物的氮原子作为亲核原子，而不是氧原子，以在温和的反应条件下构建各种亚硝酮。多种(E)-醛肟和(E)-酮肟已证明与该反应兼容，并且大多数示例中未检测到O-环开启反应的产物。
• A convenient and efficient ring-opening reaction of aziridines with acetylenes and synthesis of dihydropyrroles
  作者：Chang-Hua Ding、Li-Xin Dai、Xue-Long Hou

  DOI：10.1016/j.tet.2005.07.076

  日期：2005.10

  In the presence of tBuOK, reaction of acetylenes with N-Ts substituted aziridines derived from both cyclic and acyclic alkenes at room temperature gave rise to homopropargylamines in good to high yields and in high regioselectivity. Not only Ph- and Me3Si-substituted acetylenes but also acetylene itself was suitable reagents. Treatment of ring-opening products with I2 and AgOAc in the presence of K2CO3

  在t BuOK的存在下，乙炔与室温下衍生自环状和无环烯烃的N -Ts取代的氮丙啶反应以高至高收率和高区域选择性产生了高炔丙胺。合适的试剂不仅是Ph和Me 3 Si取代的乙炔，而且乙炔本身也是合适的试剂。在K 2 CO 3存在下用I 2和AgOAc处理开环产物以高产率提供了二氢吡咯。还可以通过在NaH存在下氮丙啶和苯乙炔的反应，然后用I 2和AgOAc处理，实现一锅合成二氢吡咯。