(Z)-N-(hex-4-en-1-yl)-4-methylbenzenesulfonamide | 906451-51-2

• 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)-N-(hex-4-en-1-yl)-4-methylbenzenesulfonamide
• 英文别名: N-[(Z)-hex-4-enyl]-4-methylbenzenesulfonamide
• CAS: 906451-51-2
• 化学式: C₁₃H₁₉NO₂S
• 分子量: 253.365
• InChiKey: STFPCZNVUDZNMC-ARJAWSKDSA-N

物化性质

• 沸点：
  373.6±45.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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)-N-(hex-4-en-1-yl)-4-methylbenzenesulfonamide 在 Oxone 作用下， 以 水 、 乙腈 为溶剂， 反应 56.0h， 以91%的产率得到(+/-)-syn-1-(1-tosylpyrrolidin-2-yl)ethanol
  参考文献：
  名称：

  Brønsted Acid-assisted Intramolecular Aminohydroxylation of N-Alkenylsulfonamides under Heavy Metal-free Conditions

  摘要：

  The intramolecular aminohydroxylation of N-alkenylsulfonamides proceeded under heavy metal-free conditions to give substituted prolinol derivatives in high yields. Oxone activated by catalytic Bronsted acid worked well as an electrophilic oxidant for this reaction.

  DOI：

  10.1021/jo301523a
• 作为产物：
  描述：

  (Z)-2-(hex-4-en-1-yl)isoindoline-1,3-dione 在 一水合肼 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 12.5h， 生成 (Z)-N-(hex-4-en-1-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Electrophilic cyclization of N-alkenylamides using a chloramine-T/I2 system

  摘要：

  A new protocol for the cyclization of N-alkenylamides using chloramine-T and iodine is described. When N-alkenylsulfonamides are treated with chloramine-T and iodine, three- to six-membered N-heterocycles are obtained with complete stereoselectivity. The method is compatible with the cyclization of the allylbenzamide or allylbenzthioamide to afford an oxazoline or thiazoline derivative, respectively. Mechanistic studies indicate that the chloramine-T/I-2 system functions as an effective iodonium species. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.003

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。
• Aza-heterocycles via copper-catalyzed, remote C–H desaturation of amines
  作者：Leah M. Stateman、Ross M. Dare、Alyson N. Paneque、David A. Nagib

  DOI：10.1016/j.chempr.2021.10.022

  日期：2022.1

  desaturation of amines. Inspired by the Hofmann-Löffler-Freytag (HLF) synthesis of five-membered pyrrolidines, we tackled the century-old challenge of synthesizing six-membered piperidines by H-atom transfer. Herein, we present a double, vicinal C–H oxidation by dual catalysis, entailing Ir photocatalytic initiation of 1,5-HAT by an N-centered radical and Cu-catalyzed interception of the C-centered radical

  大多数药物在五元或六元环中含有一个氮原子。为了快速获得这两种氮杂杂环化合物，我们试图开发一种远程 C-H 胺去饱和方法。受五元吡咯烷的 Hofmann-Löffler-Freytag (HLF) 合成的启发，我们解决了通过氢原子转移合成六元哌啶的百年挑战。在这里，我们提出了一个 双，通过双催化进行邻位 C-H 氧化，需要 Ir 光催化引发 1,5-HAT 由 N 中心自由基和 Cu 催化拦截 C 中心自由基以促进去饱和。通过这种机制，两个 C-H 键（δ 和 ε 到 N）被区域选择性地从烷基链的无偏、远程位置移除。超过 50 个实例说明了合成内部和末端 δ 乙烯基胺和氮杂杂环的效率、选择性、官能团耐受性和药用价值。机理实验探索了烷基铜中间体，以及 HAT 和消除步骤的动力学和区域选择性。
• A New, Simple Synthesis of <i>N</i>-Tosyl Pyrrolidines and Piperidines
  作者：Maria Marcotullio、Valerio Campagna、Silvia Sternativo、Ferdinando Costantino、Massimo Curini

  DOI：10.1055/s-2006-942488

  日期：2006.8

  lodocyclization of unsaturated tosylamides promoted by Oxone® oxidation of KI afforded, in good yields, N-tosyl iodopyrrolidines and piperidines. A new, simple method for the conversion of alcohols to tosylamides is presented.

  通过 Oxone® 氧化 KI 促进的不饱和甲苯磺酰胺的碘环化以良好的收率提供了 N-甲苯磺酰基碘吡咯烷和哌啶。介绍了一种将醇转化为甲苯磺酰胺的简单新方法。
• Practical Synthesis of Halogenated <i>N</i> ‐Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes
  作者：Yanyang He、Xiaowen Qin、Xinxu He、Xiao‐Feng Wu、Zhiping Yin

  DOI：10.1002/ejoc.202101189

  日期：2021.11.15

  A general and efficient intramolecular halo-amination of unactivated alkenes for the synthesis of various halogenated N-heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N-heterocycles, including three-, five-, and six-membered N-heterocycles were

  通过电化学阳极氧化开发了用于合成各种卤化N-杂环的未活化烯烃的通用且有效的分子内卤化胺化。该协议通过使用 LiI 或 LiBr 作为氧化还原介质和卤素源，在一个简单的未分隔单元中进行。在室温下以中等至良好的产率构建了范围广泛的卤化N-杂环，包括三元、五元和六元N-杂环。值得注意的是，这种电化学氧化转化避免了使用外部氧化剂和强碱，因此代表了一种环境友好的方法。
• Practical and Convenient Synthesis of <i>N</i>-Heterocycles:  Stereoselective Cyclization of <i>N</i>-Alkenylamides with <i>t</i>-BuOI under Neutral Conditions
  作者：Satoshi Minakata、Yoshinobu Morino、Yoji Oderaotoshi、Mitsuo Komatsu

  DOI：10.1021/ol061182q

  日期：2006.7.1

  [Structure: see text] tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cyclization of N-alkenylamides leading to a variety of N-heterocycles under extremely mild conditions. When N-alkenylsulfonamides were employed in the reaction, three- to six-membered saturated N-heterocycles were obtained in good to excellent yields with complete stereoselectivity. The method was applicable

  [结构：见正文]叔丁基次碘酸盐（t-BuOI）被发现是在极端温和条件下环化N-烯基酰胺的强大试剂，可导致多种N-杂环。当在反应中使用N-烯基磺酰胺时，以完全的立体选择性，以良好至优异的产率获得了三元至六元饱和N-杂环。该方法适用于烯基苯甲酰胺衍生物的环化以提供N-，O-或N-，S-杂环。