N-(4-toluenesulfonyl)-(Z)-4-(4-methylphenyl)but-3-enylamine | 428453-35-4

• 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-toluenesulfonyl)-(Z)-4-(4-methylphenyl)but-3-enylamine
• 英文别名: (Z)-4-methyl-N-(4-(p-tolyl)but-3-en-1-yl)benzenesulfonamide
• CAS: 428453-35-4
• 化学式: C₁₈H₂₁NO₂S
• 分子量: 315.436
• InChiKey: NNYLNETYXLUHRD-HYXAFXHYSA-N

物化性质

• 沸点：
  493.4±55.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(4-toluenesulfonyl)-(Z)-4-(4-methylphenyl)but-3-enylamine 在 三氟甲磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以77%的产率得到N-(4-甲苯磺酰基)-2-(4-甲基苯基)吡咯烷
  参考文献：
  名称：

  Brønsted Acid-Catalyzed Intramolecular Hydroamination of Protected Alkenylamines. Synthesis of Pyrrolidines and Piperidines

  摘要：

  [GRAPHIC]The cyclization of aminoalkenes bearing an electron-withdrawing group on the nitrogen atom was catalyzed by triflic or sulfuric acid in toluene. Pyrrolidines and piperidines were formed in excellent yields. N-Phenylanilides also underwent cyclization to form gamma-lactams.

  DOI：

  10.1021/ol025659j
• 作为产物：
  描述：

  (Z)-N-(4-(4-methylphenyl)but-3-enyl)phthalimide 在 一水合肼 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 N-(4-toluenesulfonyl)-(Z)-4-(4-methylphenyl)but-3-enylamine
  参考文献：
  名称：

  Brønsted Acid-Catalyzed Intramolecular Hydroamination of Protected Alkenylamines. Synthesis of Pyrrolidines and Piperidines

  摘要：

  [GRAPHIC]The cyclization of aminoalkenes bearing an electron-withdrawing group on the nitrogen atom was catalyzed by triflic or sulfuric acid in toluene. Pyrrolidines and piperidines were formed in excellent yields. N-Phenylanilides also underwent cyclization to form gamma-lactams.

  DOI：

  10.1021/ol025659j

文献信息

• Alkene Oxyamination Using Malonoyl Peroxides: Preparation of Pyrrolidines and Isoxazolidines
  作者：Carla Alamillo-Ferrer、Jonathan M. Curle、Stuart C. Davidson、Simon C. C. Lucas、Stephen J. Atkinson、Matthew Campbell、Alan R. Kennedy、Nicholas C. O. Tomkinson

  DOI：10.1021/acs.joc.8b00392

  日期：2018.6.15

  functionalized pyrrolidines and isoxazolidines. This metal free alkene oxyamination proceeds in 50–85% yield and up to 13:1 trans-selectivity. In addition, the relative stereochemistry of the oxygen and nitrogen substituents can be inverted through an oxidation/reduction sequence or inverting the stereochemistry of the starting alkene. Mechanistic investigations show a higher reactivity for hydroxyl

  高烯丙基的治疗Ñ甲苯磺酰胺或烯丙基ñ -tosyl用的过氧化物malonoyl 1.5当量羟胺提供一种立体选择性的方法来访问官能吡咯烷和异恶唑烷。这种无金属的烯烃氧胺化反应收率可达50-85％，反式选择性高达13：1 。另外，氧和氮取代基的相对立体化学可以通过氧化/还原序列或起始烯烃的立体化学来反转。机理研究表明，羟基亲核试剂比磺酰胺亲核试剂具有更高的反应性，表明对双加氧反应的偏好高于对氧胺的反应。
• Palladium-catalyzed inter- and intramolecular hydroamination of styrenes coupled with alcohol oxidation using N-fluorobenzenesulfonimide as the oxidant
  作者：Tao Xu、Shuifa Qiu、Guosheng Liu

  DOI：10.1016/j.jorganchem.2010.07.015

  日期：2011.1

  Palladium-catalyzed inter- and intramolecular hydroaminations of styrenes that are coupled to alcohol oxidation under oxidative condition are reported. The fluorination reagent NFSI is used as the nitrogen source as well as the oxidant. Bidental nitrogen ligand bathocuproine plays a crucial role in this transformation. (C) 2010 Elsevier B.V. All rights reserved.