(E)-N,4-dimethyl-N-(4-phenylbut-3-en-1-yn-1-yl)benzenesulfonamide | 1562381-12-7

• 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: (E)-N,4-dimethyl-N-(4-phenylbut-3-en-1-yn-1-yl)benzenesulfonamide
• 英文别名: N,4-dimethyl-N-[(E)-4-phenylbut-3-en-1-ynyl]benzenesulfonamide
• CAS: 1562381-12-7
• 化学式: C₁₈H₁₇NO₂S
• 分子量: 311.404
• InChiKey: MBWQDHCPCSZWFT-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N,4-dimethyl-N-(4-phenylbut-3-en-1-yn-1-yl)benzenesulfonamide 在 1,3-双(2,6-二-异丙基苯基)咪唑-2-亚基金(I)氯化物 、 碘 、 silver sulfate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 N-(6-(dimethylamino)-3-iodo-5-phenylpyridin-2-yl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  乙酰胺和氰胺的杂-Tetradehydro-Diels-Alder环加成反应：金催化生成的不同取代的2,6-二氨基吡啶

  摘要：

  金（I）催化的乙酰胺和氰酰胺杂四-脱氢-狄尔斯-阿尔德环加成反应是制备不同取代的2,6-二氨基吡啶的有效途径（28个实例；产率高达99％）。反应在具有高官能团耐受性的非常温和的条件下（DCM，rt）进行。所获得的2，6-二氨基吡啶代表有用的合成平台，其具有易于调节的取代模式，用于吡啶核和N-取代基的随后官能化。

  DOI：

  10.1021/acs.joc.1c00558
• 作为产物：
  描述：

  (E)-but-1-en-3-yn-1-ylbenzene 在 N-溴代丁二酰亚胺(NBS) 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 silver nitrate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 1.0h， 生成 (E)-N,4-dimethyl-N-(4-phenylbut-3-en-1-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Zn(II)- or Ag(I)-Catalyzed 1,4-Metathesis Reactions between 3-En-1-ynamides and Nitrosoarenes

  摘要：

  Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 2-propynimidamides and benzaldehyde derivatives. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently. We have developed metathesis/alkynation cascades for unsubstituted 2-propynimidamides and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes. Both 1,4-oxoiminations and 1,4-hydroxyiminations increase the molecular complexity of products.

  DOI：

  10.1021/ja412634w

文献信息

• Acid-catalyzed [2 + 2 + 2] cycloaddition of two cyanamides and one ynamide: highly regioselective synthesis of 2,4,6-triaminopyrimidines
  作者：Alexey Yu. Dubovtsev、Valeria V. Zvereva、Nikolay V. Shcherbakov、Dmitry V. Dar'in、Alexander S. Novikov、Vadim Yu. Kukushkin

  DOI：10.1039/d1ob00513h

  日期：——

  Triflic acid (10 mol%) catalyzes the highly regioselective [2 + 2 + 2] cycloaddition between two cyanamides and one ynamide to grant the 2,4,6-triaminopyrimidine core. The developed synthetic method is effective for the preparation of a family of the diversely substituted heterocyclic products (30 examples; yields up to 94%). The synthesis can be easily scaled up and conducted in gram quantities. As

  三氟甲磺酸 (10 mol%) 催化两个氰胺和一个 ynamide 之间的高度区域选择性 [2 + 2 + 2] 环加成，形成 2,4,6-三氨基嘧啶核心。所开发的合成方法对于制备一系列不同取代的杂环产品是有效的（30 个例子；产率高达 94%）。该合成可以很容易地放大并以克的数量进行。正如涉及氨基取代基的后官能化所证明的，所获得的杂环代表了构建各种嘧啶基框架的有用平台。所进行的密度泛函理论计算证实了 H +在环加成的区域选择性中作为亲电活化剂的特殊作用。
• Chiral Bifunctional Phosphine Ligand Enables Asymmetric Trapping of Catalytic Vinyl Gold Carbene Species
  作者：Xuan Wu、Ke Zhao、Carlos D. Quintanilla、Liming Zhang

  DOI：10.1021/jacs.3c10865

  日期：2024.1.31

  employing alkyne/allene as the electrophilic site, this work engages an in situ-generated alkenyl/acyl gold carbene in a ligand-facilitated attack by an alcoholic nucleophile. With an amide-functionalized chiral binaphthylphosphine ligand, γ-alkoxy-α,β-unsaturated imides are formed with excellent enantiomeric excesses. The intermediacy of a carbene species is supported by its alternative access via dediazotization

  双功能配体支持的协同金催化可加速亲核攻击，并提供实现不对称金催化的通用策略。与之前使用炔烃/烯烯作为亲电位点的研究不同，这项工作在醇亲核试剂的配体促进攻击中利用原位生成的烯基/酰基金卡宾。与酰胺官能化的手性联萘基膦配体一起，γ-烷氧基-α，β-不饱和酰亚胺以优异的对映体过量形成。卡宾物种的中间体由其通过脱重氮化的替代途径支持。该反应可耐受多种醇类，除芳纶酰胺外，还可以容纳二烯酰胺底物。这项工作利用一种多功能策略来富集金化学，并通过配体促进的反应性中间体的对映选择性捕获实现具有挑战性的对映选择性金催化。
• Hetero-Tetradehydro-Diels–Alder Cycloaddition of Enynamides and Cyanamides: Gold-Catalyzed Generation of Diversely Substituted 2,6-Diaminopyridines
  作者：Nikolay V. Shcherbakov、Dmitry V. Dar’in、Vadim Yu. Kukushkin、Alexey Yu. Dubovtsev

  DOI：10.1021/acs.joc.1c00558

  日期：2021.5.21

  hetero-tetradehydro-Diels–Alder cycloaddition of enynamides and cyanamides comprises an efficient route to diversely substituted 2,6-diaminopyridines (28 examples; yields up to 99%). The reaction proceeds under very mild conditions (DCM, rt) with high functional group tolerance. The obtained 2,6-diaminopyridines represent a useful synthetic platform with an easily modulated substitution pattern for subsequent

  金（I）催化的乙酰胺和氰酰胺杂四-脱氢-狄尔斯-阿尔德环加成反应是制备不同取代的2,6-二氨基吡啶的有效途径（28个实例；产率高达99％）。反应在具有高官能团耐受性的非常温和的条件下（DCM，rt）进行。所获得的2，6-二氨基吡啶代表有用的合成平台，其具有易于调节的取代模式，用于吡啶核和N-取代基的随后官能化。
• Zn(II)- or Ag(I)-Catalyzed 1,4-Metathesis Reactions between 3-En-1-ynamides and Nitrosoarenes
  作者：Sagar Ashok Gawade、Deepak B. Huple、Rai-Shung Liu

  DOI：10.1021/ja412634w

  日期：2014.2.26

  Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 2-propynimidamides and benzaldehyde derivatives. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently. We have developed metathesis/alkynation cascades for unsubstituted 2-propynimidamides and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes. Both 1,4-oxoiminations and 1,4-hydroxyiminations increase the molecular complexity of products.