thiophene-2-sulfonic acid allylamide | 140938-40-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: thiophene-2-sulfonic acid allylamide
• 英文别名: N-allylthiophene-2-sulfonamide；Thiophen-2-sulfonsaeure-allylamid；N-(prop-2-en-1-yl)thiophene-2-sulfonamide；N-prop-2-enylthiophene-2-sulfonamide
• CAS: 140938-40-5
• 化学式: C₇H₉NO₂S₂
• mdl: MFCD02047253
• 分子量: 203.286
• InChiKey: AUHGVYZXVHHKGB-UHFFFAOYSA-N

物化性质

• 熔点：
  54-56 °C
• 沸点：
  324.2±44.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  82.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  thiophene-2-sulfonic acid allylamide 在 (R,R)-QuinoxP 、 sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate 、 potassium carbonate 、 cobalt(II) bromide 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.0h， 生成 (R,Z)-2-((4-benzylidene-1-(thiophen-2-ylsulfonyl)pyrrolidin-3-yl)methyl)-1-(pyridin-2-yl)-1H-indole
  参考文献：
  名称：

  Cobalt-Catalyzed Enantioselective Hydroarylation of 1,6-Enynes

  摘要：

  An asymmetric hydroarylative cyclization of enynes involving a C-H bond cleavage is reported. The cobalt-catalyzed cascade generates three new bonds in an atom-economical fashion. The products were obtained in excellent yields and excellent enantioselectivities as single diastereo- and regioisomers. Preliminary mechanistic studies indicate that the reaction shows no intermolecular C-H crossover. This work highlights the potential of cobalt catalysis in C-H bond functionalization and enantioselective domino reactivity.

  DOI：

  10.1021/jacs.0c03246
• 作为产物：
  描述：

  丙烯胺 、 Pyridine;thiophene-2-sulfonic acid 在 trifluoromethanesulfonic acid anhydride 、 三苯基氧化膦 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到thiophene-2-sulfonic acid allylamide
  参考文献：
  名称：

  从磺酸直接合成磺酰胺和活化磺酸酯

  摘要：

  描述了通过使用三苯基膦二三氟甲磺酸酯试剂直接偶联磺酸盐与胺和醇来制备磺酰胺和活化磺酸酯的通用新方法。还描述了一种新的可重复使用的聚合物支持的试剂，用于在异质条件下进行这些转化。这些方法为制备含有磺酰胺官能团的小分子提供了一种全新的方法。

  DOI：

  10.1021/ja0397658

文献信息

• Cobalt‐Catalyzed Cascade Reaction of Ynamides and 1,3‐Dicarbonyl Compounds for Selective Synthesis of Differently Sized <i>N</i> ‐Heterocycles
  作者：Biao Zhang、Xu‐Heng Yang、Jian Huang、Cheng‐an Tao、Jianfang Wang

  DOI：10.1002/adsc.202201002

  日期：2023.3.7

  manifold with various 1,3-dicarbonyl compounds and halogenated N-allyl ynamides was accomplished under alkaline reaction conditions, facilitating the synthesis of differently sized N-heterocycles. A large array of products was prepared to demonstrate the selective synthesis of N-heterocycles of different ring sizes (5-, 6-, and 7-membered rings) via cobalt catalysis. The reaction has broad substrate

  在碱性反应条件下完成了具有各种 1,3-二羰基化合物和卤代N-烯丙基酰胺的三苯基膦连接的钴催化环化歧管，促进了不同大小的N-杂环的合成。准备了大量的产品来证明通过钴催化选择性合成不同环大小（5、6 和 7 元环）的N-杂环。该反应具有广泛的底物范围和广泛的官能团。
• Visible‐Light‐Induced Diradical‐Mediated <i>ipso</i> ‐Cyclization towards Double Dearomative [2+2]‐Cycloaddition or Smiles‐Type Rearrangement
  作者：Guangjin Zhen、Guohui Zeng、Kai Jiang、Furong Wang、Xiaohui Cao、Biaolin Yin

  DOI：10.1002/chem.202203217

  日期：2023.3.13

  ipso-cyclization involving dearomatizing spiro-intermediates of aromatic compounds towards divergent reaction pathways deserves investigation but has been rarely reported so far. By tuning the rate of C−S bond cleavage in the key dearomatizing spiro intermediate, a chemical divergent reaction of (hetero)aryl sulfonamides has been achieved in a visible-light-induced energy transfer reaction pathway involving diradical

  双自由基介导的 ipso环化涉及将芳香族化合物的螺环中间体脱芳构化到不同的反应途径值得研究，但迄今为止很少有报道。通过调节关键的脱芳构化螺环中间体中 C-S 键的断裂速率，在涉及双自由基物种的可见光诱导能量转移反应途径中实现了（杂）芳基磺酰胺的化学发散反应。
• Tunable [3+2] and [4+2] annulations for pyrrolidine and piperidine synthesis
  作者：Jeewani P. Ariyarathna、Prabagar Baskaran、Akanksha Chhikara、Navdeep Kaur、Alex M. Nguyen、Shashini M. Premathilaka、Michelle M. Huynh、Jonathon T. Truong、Wei Li

  DOI：10.1039/d3cc01400b

  日期：——

  N-heterocycles are privileged pharmaceutical scaffolds in drug discovery and development. We disclose here divergent intermolecular coupling strategies that can access diverse N-heterocycles directly from olefins. The radical-to-polar mechanistic switching is key for the divergent cyclization processes. These distinctive annulations result in the coupling of alkenes with simple bifunctional reagents

  N-杂环是药物发现和开发中的重要药物支架。我们在这里公开了不同的分子间偶联策略，可以直接从烯烃获得不同的N-杂环。自由基到极性的机制转换是不同环化过程的关键。这些独特的环化导致烯烃与简单的双功能试剂偶联，用于不同的 N-杂环合成。
• Foye et al., Journal of the American Pharmaceutical Association (1912), 1952, vol. 41, p. 273,275
  作者：Foye et al.

  DOI：——

  日期：——
• Asymmetric Organocatalytic Allylic Substitution of Morita–Baylis–Hillman Carbonates with Allylamines for the Synthesis of 2,5-Dihydropyrroles
  作者：Wangsheng Sun、Xiaozhou Ma、Liang Hong、Rui Wang

  DOI：10.1021/jo2011522

  日期：2011.10.7

  The asymmetric allylic substitution reaction of MBH carbonates with allylamines has been developed, which affords N-allyl-beta-amino-alpha-methylene esters in high yields and enantioselectivities. After a subsequent ring-closure metathesis of the products, a series of optically active 2,5-dihydropyrroles could be obtained smoothly in high yields without any loss of enantioselectivity. Finally, a tentative mechanism for rationalization of the reaction has been proposed.