4-methyl-N-(3-methyl-1-phenylbut-3-enyl)benzenesulfonamide | 172910-15-5

• 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: 4-methyl-N-(3-methyl-1-phenylbut-3-enyl)benzenesulfonamide
• 英文别名: N-(1-phenyl-3-methylbut-3-enyl)-p-toluensulfonamide
• CAS: 172910-15-5
• 化学式: C₁₈H₂₁NO₂S
• 分子量: 315.436
• InChiKey: WTYKUBFLIYEMPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  4-methyl-N-(3-methyl-1-phenylbut-3-enyl)benzenesulfonamide 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  烯丙基酯的串联酰氧基迁移/分子内[3 + 2]环加成反应生成金催化的哌啶合成

  摘要：

  已经开发了一种Au催化串联方案，该方案涉及烯丙基酯异构化和随后的分子内[3 + 2]环化。该策略为多官能哌啶的合成提供了一种有效的方法，所述多官能哌啶是许多生物活性分子的亚基。

  DOI：

  10.1021/ol202746s
• 作为产物：
  描述：

  对甲苯磺酰胺 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 4-methyl-N-(3-methyl-1-phenylbut-3-enyl)benzenesulfonamide
  参考文献：
  名称：

  铁催化三组分磺酰胺基化反应组装高烯丙胺衍生物

  摘要：

  醛，磺酰胺和烯丙基硅烷之间实现了有效的FeCl 3催化的三组分反应，这为构建均烯丙基胺衍生物提供了便捷，原子经济和绿色的方式。此外，该反应与γ-取代的烯丙基硅烷表现出优异的顺式立体选择性。

  DOI：

  10.1002/aoc.3334

文献信息

• Gold-catalyzed cycloisomerizations of ene-ynamides
  作者：Sylvain Couty、Christophe Meyer、Janine Cossy

  DOI：10.1016/j.tet.2008.10.108

  日期：2009.2

  The gold-catalyzed cycloisomerizations of 1,6-ene-ynamides proceed under mild conditions and lead to cyclobutanones from terminal or trimethylsilyl substituted ynamides, or to carbonyl compounds bearing a 2,3-methanopyrrolidine subunit from substrates possessing a propargylic alcohol moiety. High diastereoselectivities are observed with 1,6-ene-ynamides having a stereocenter at the α or β position

  1，6-烯-酰胺的金催化的环异构化在温和的条件下进行，并从末端或三甲基甲硅烷基取代的酰胺中产生环丁酮，或从具有炔丙醇部分的底物上产生带有2,3-甲基吡咯烷亚基的羰基化合物。用在氮原子的α或β位置具有立体中心的1，6-烯-酰胺具有高的非对映选择性。
• Efficient Ring-Closing Metathesis of Alkenyl Bromides: The Importance of Protecting the Catalyst during the Olefin Approach
  作者：Michele Gatti、Emma Drinkel、Linglin Wu、Ivano Pusterla、Fiona Gaggia、Reto Dorta

  DOI：10.1021/ja108253f

  日期：2010.11.3

  We present the first productive ring-closing metathesis reaction that leads to the construction of cyclic alkenyl bromides. Efficient catalysis employing commercially available Grubbs II catalyst is possible through appropriate modification of the starting bromoalkene moiety.
• Convenient Syntheses of Chiral Cyclic Sulfinates (Sultines) from Unsaturated Alcohols
  作者：Charles M. Marson、Paul R. Giles

  DOI：10.1021/jo00129a056

  日期：1995.12

  The reaction of unsaturated alcohols with N-sulfinyl-p-toluenesulfonamide (TsNSO) is shown to lead stereoselectively to chiral cyclic or bicyclic sulfinates (sultines). The reactions occur at ambient temperatures and afford a general route to delta- and epsilon-sultines which are notable for their crystallinity and thermal stability. These studies confirm the preservation of stereochemical integrity of the carbon atom alpha to the oxygen atom in the sultine ring. Some unsaturated aldehydes furnish sultines via a tandem oxo-ene cyclization and subsequent ring closure to the sultine. In some reactions, N-toluenesulfonamide derivatives of sultines (compounds of type 11) were isolated, and since those were converted into the sultines by the action of BF3-OEt(2), such sulfonamides are considered to be intermediates in the reaction pathway.
• Au-Catalyzed Piperidine Synthesis via Tandem Acyloxy Migration/Intramolecular [3 + 2] Cycloaddition of Enynyl Esters
  作者：Huaiji Zheng、Xing Huo、Changgui Zhao、Peng Jing、Juan Yang、Bowen Fang、Xuegong She

  DOI：10.1021/ol202746s

  日期：2011.12.16

  An Au-catalyzed tandem protocol involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach for the synthesis of polyfunctional piperidines, which are subunits of many bioactive molecules.

  已经开发了一种Au催化串联方案，该方案涉及烯丙基酯异构化和随后的分子内[3 + 2]环化。该策略为多官能哌啶的合成提供了一种有效的方法，所述多官能哌啶是许多生物活性分子的亚基。
• Assembly of homoallylamine derivatives through iron-catalyzed three-component sulfonamidoallylation reaction
  作者：Xiaohui Fan、Hong-Bo Zhu、Hao Lv、Kun Guo、Yong-Hong Guan、Xiao-Meng Cui、Bin An、Yan-Ling Pu

  DOI：10.1002/aoc.3334

  日期：2015.9

  An efficient FeCl3‐catalyzed three‐component reaction between aldehydes, sulfonamides and allylsilanes has been achieved, which provides a convenient, atom‐economic and green way to construct homoallylamine derivatives. In addition, this reaction exhibits excellent syn stereoselectivity with γ‐substituted allylsilanes.

  醛，磺酰胺和烯丙基硅烷之间实现了有效的FeCl 3催化的三组分反应，这为构建均烯丙基胺衍生物提供了便捷，原子经济和绿色的方式。此外，该反应与γ-取代的烯丙基硅烷表现出优异的顺式立体选择性。