N-(2-(3-oxobut-1-en-1-yl)phenyl)formamide | 1379407-24-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-(2-(3-oxobut-1-en-1-yl)phenyl)formamide
• CAS: 1379407-24-5
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: DGBVCBAOWVOZNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2-(3-oxobut-1-en-1-yl)phenyl)formamide 在 联苯二碲 、 二异丙胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 2-phenylsulfanyl-3-((acetyl)(phenylsulfanyl)methyl)-1H-indole
  参考文献：
  名称：

  Photoinduced Intramolecular Cyclization of o-Ethenylaryl Isocyanides with Organic Disulfides Mediated by Diphenyl Ditelluride

  摘要：

  Photoinduced reaction of o-ethenylaryl isocyanides with organic disulfides in the presence of diphenyl ditellurides affords the corresponding bisthiolated indole derivatives via a radical cyclization process. The cyclization can proceed at room temperature upon visible-light irradiation and exhibits good tolerance to functional groups. Several organic disulfides also can be employed for this cyclization, and the corresponding bisthiolated indole derivatives are obtained selectively. In addition, the photoinduced reaction of o-ethenylaryl isocyanides with bis(2-aminophenyl) disulfide affords tetracyclic compounds in one portion.

  DOI：

  10.1021/jo200299d
• 作为产物：
  描述：

  2-溴苯胺 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 22.0h， 生成 N-(2-(3-oxobut-1-en-1-yl)phenyl)formamide
  参考文献：
  名称：

  Photoinduced Intramolecular Cyclization of o-Ethenylaryl Isocyanides with Organic Disulfides Mediated by Diphenyl Ditelluride

  摘要：

  Photoinduced reaction of o-ethenylaryl isocyanides with organic disulfides in the presence of diphenyl ditellurides affords the corresponding bisthiolated indole derivatives via a radical cyclization process. The cyclization can proceed at room temperature upon visible-light irradiation and exhibits good tolerance to functional groups. Several organic disulfides also can be employed for this cyclization, and the corresponding bisthiolated indole derivatives are obtained selectively. In addition, the photoinduced reaction of o-ethenylaryl isocyanides with bis(2-aminophenyl) disulfide affords tetracyclic compounds in one portion.

  DOI：

  10.1021/jo200299d

文献信息

• Synthesis of 2-Boryl- and Silylindoles by Copper-Catalyzed Borylative and Silylative Cyclization of 2-Alkenylaryl Isocyanides
  作者：Mamoru Tobisu、Hirokazu Fujihara、Keika Koh、Naoto Chatani

  DOI：10.1021/jo101024f

  日期：2010.7.16

  2-borylindoles via the copper(I)-catalyzed borylative cyclization of 2-alkenylphenyl isocyanides using diboronate. The reaction proceeds at room temperature under neutral conditions and exhibits high tolerance to functional groups, such as Br, CO2R, COR, CONMe2, and CN. The 2-borylindoles synthesized in the present study can be elaborated into an array of indole-based derivatives, for example, through the

  我们已经开发了一种通过使用二硼酸酯经铜（I）催化的2-烯基苯基异氰酸酯的硼化环化来合成2-硼吲哚的方法。反应在室温，中性条件下进行，并且对Br，CO 2 R，COR，CONMe 2等官能团具有较高的耐受性和CN。在本研究中合成的2-硼基吲哚可以通过例如Suzuki-Miyaura反应合成为一系列基于吲哚的衍生物。该方法的实用性在激酶抑制剂paullone的快速合成中得到了证明。通过分别使用氢硼酸酯（或氢硅烷）和甲硅烷基硼酸酯，可以将反应扩展到2-氢化吲哚和2-甲硅烷基吲哚的合成。在这些铜催化的条件下，也可以通过使用1,2-异氰基苯作为底物来构建喹喔啉环系统。
• Silver-catalyzed P-centered anion nucleophilic addition to isocyanide: access to 2-phosphinoyl indoles/indol-3-ols
  作者：Yong Liu、Mengying Jia、Guodong Wang、Wenhui Yang、Xianxiu Xu

  DOI：10.1039/d4cc01984a

  日期：——

  nucleophilic addition of a P-centered anion to isocyanides and cyclization reaction was developed for the efficient and practical synthesis of a wide range of 2-phosphinoyl indole and indol-3-ol derivatives. Unlike the well-documented synthesis of phosphorus-functionalized heterocycles via a P-centered radical, an anionic reactivity profile of phosphine oxides is most likely involved in this domino transformation

  开发了银催化的以 P 为中心的阴离子与异氰化物的化学选择性级联亲核加成和环化反应，用于有效且实用地合成各种 2-膦酰基吲哚和吲哚-3-醇衍生物。与通过P 中心自由基合成磷官能化杂环不同，氧化膦的阴离子反应性特征很可能参与这种多米诺骨牌转化。