(Z)-4-methyl-N-(4-phenylbut-3-en-1-yl)benzenesulfonamide | 428453-34-3

• 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: (Z)-4-methyl-N-(4-phenylbut-3-en-1-yl)benzenesulfonamide
• 英文别名: 4-methyl-N-[(Z)-4-phenylbut-3-enyl]benzenesulfonamide
• CAS: 428453-34-3
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: WMEWTZWNRSQQJQ-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-4-methyl-N-(4-phenylbut-3-en-1-yl)benzenesulfonamide 在 十八氟十氢萘 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 1.0h， 以91%的产率得到2-苯基-1-(4-甲基苯磺酰)吡咯烷
  参考文献：
  名称：

  Heptadecafluorooctanesulfonic acid (C8F17SO3H) catalyzed intramolecular hydroamination of olefinic sulfonamides in fluorous biphase system (FBS)

  摘要：

  A practical, efficient, and environmentally benign intramolecular hydroamination of olefinic sulfonamides was carried out in fluorous biphase system (FBS) using commercially available heptadecafluorooctanesulfonic acid (C8F17SO3H) as a catalyst and perfluorodecaline (C10F18, cis- and trans- mixture) as a fluorous solvent to produce the corresponding cyclic products in good yields. The Bronsted acid of C8F17SO3H is easily recovered and recycled at least five times. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2006.09.012
• 作为产物：
  描述：

  N-(3-bromopropyl)-4-methylbenzenesulfonamide 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 对二甲苯 为溶剂， 反应 14.0h， 生成 (Z)-4-methyl-N-(4-phenylbut-3-en-1-yl)benzenesulfonamide
  参考文献：
  名称：

  铜催化的三氟甲基化四氢呋喃的非对映选择性合成

  摘要：

  在温和的条件下，使用Togni试剂作为三氟甲基化试剂，实现了铜催化的均丙醇的分子内非对映选择性三氟甲基环醚化。以中等至良好的产率合成了各种三氟甲基化的四氢呋喃。而且，宽泛的通用官能团是可以容忍的。

  DOI：

  10.1002/adsc.201501166

文献信息

• Palladium- and Ruthenium-Catalyzed Cycloisomerization of Enynamides and Enynhydrazides: A Rapid Approach to Diverse Azacyclic Frameworks
  作者：P. Ross Walker、Craig D. Campbell、Abid Suleman、Greg Carr、Edward A. Anderson

  DOI：10.1002/anie.201304186

  日期：2013.8.26

  I want to ride my azacycle: The title reaction of enynamides affords a wide diversity of azacycles. The reactions are high‐yielding, highly stereoselective, and proceed rapidly under mild reaction conditions. Equivalent transformations using enynhydrazides offer new routes to pyrazole and indazole scaffolds. Boc=tert‐butoxycarbonyl, EWG=electron‐withdrawing group, Ns=4‐nitrobenzenesulfonyl, Ts=4‐toluenesulfonyl

  我想骑着氮杂自行车：烯乙酰胺的标题反应提供了多种氮杂自行车。反应具有高产率，高立体选择性，并且在温和的反应条件下可以快速进行。使用烯丙肼的等效转化为吡唑和吲唑支架的开发提供了新途径。Boc =叔丁氧羰基，EWG =吸电子基团，Ns = 4-硝基苯磺酰基，Ts = 4-甲苯磺酰基。
• Brønsted Acid-Catalyzed Intramolecular Hydroamination of Protected Alkenylamines. Synthesis of Pyrrolidines and Piperidines
  作者：Björn Schlummer、John F. Hartwig

  DOI：10.1021/ol025659j

  日期：2002.5.1

  [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.
• Heptadecafluorooctanesulfonic acid (C8F17SO3H) catalyzed intramolecular hydroamination of olefinic sulfonamides in fluorous biphase system (FBS)
  作者：Yan Yin、Gang Zhao

  DOI：10.1016/j.jfluchem.2006.09.012

  日期：2007.1

  A practical, efficient, and environmentally benign intramolecular hydroamination of olefinic sulfonamides was carried out in fluorous biphase system (FBS) using commercially available heptadecafluorooctanesulfonic acid (C8F17SO3H) as a catalyst and perfluorodecaline (C10F18, cis- and trans- mixture) as a fluorous solvent to produce the corresponding cyclic products in good yields. The Bronsted acid of C8F17SO3H is easily recovered and recycled at least five times. (c) 2006 Elsevier B.V. All rights reserved.
• 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.
• Copper-Catalyzed Diastereoselective Synthesis of Trifluoromethylated Tetrahydrofurans
  作者：Yanan Wang、Min Jiang、Jin-Tao Liu

  DOI：10.1002/adsc.201501166

  日期：2016.4.14

  The copper‐catalyzed intramolecular diastereoselective trifluoromethylcycloetherification of homoallylic alcohols with Togni’s reagent as trifluoromethylating reagent was realized under mild conditions. Various trifluoromethylated tetrahydrofurans were synthesized in moderate to good yields. Moreover, a wide range of common functional groups was tolerated.

  在温和的条件下，使用Togni试剂作为三氟甲基化试剂，实现了铜催化的均丙醇的分子内非对映选择性三氟甲基环醚化。以中等至良好的产率合成了各种三氟甲基化的四氢呋喃。而且，宽泛的通用官能团是可以容忍的。