N,N-diethyl-2-phenyl-1H-indole-1-carboxamide | 858647-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N,N-diethyl-2-phenyl-1H-indole-1-carboxamide
• 英文别名: N,N-diethyl-2-phenylindole-1-carboxamide
• CAS: 858647-69-5
• 化学式: C₁₉H₂₀N₂O
• 分子量: 292.381
• InChiKey: MIVRVHBGDKGLNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-2-phenyl-1H-indole-1-carboxamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到N,N-二乙基-2-(1H-吲哚-2-基)苯甲酰胺
  参考文献：
  名称：

  Anionic Indole N-Carbamoyl N → C Translocation. A Directed remote Metalation Route to 2-Aryl- and 2-Heteroarylindoles. Synthesis of Benz[a]carbazoles and Indeno[1,2-b]indoles

  摘要：

  A new LDA-induced anionic N-C carbamoyl migration of 2-arylindoles (7) is reported. Treatment of N-carbamoylindoles 10 and 13, readily available by direct and ipso-borodesilylative Suzuki-Miyaura cross-coupling routes from 8 and 12, respectively, provides a general route to functionalized 2-arylindoles 11 and 14, respectively (Tables 1 and 2). The reaction has been applied to the synthesis of benzo[a]carbazoles 16 and indeno[1,2-b]indoles 18, and its intramolecularity has been established by a crossover experiment (Scheme 4).

  DOI：

  10.1021/ol800307g
• 作为产物：
  描述：

  碘苯 、 N，N-二乙基-2-（三甲基甲硅烷基）吲哚-1-羧酰胺 在 四(三苯基膦)钯 三溴化硼 、 sodium carbonate 作用下， 以 二氯甲烷 、 乙二醇二甲醚 为溶剂， 反应 5.0h， 以85%的产率得到N,N-diethyl-2-phenyl-1H-indole-1-carboxamide
  参考文献：
  名称：

  有指导的基于原位金属化的方法。卤代，亚硝基和硼基诱导的ipso-去甲硅烷基化。链接到原位Suzuki反应。

  摘要：

  [反应：请参见文本]在标准的亲电子卤化条件下处理DoM衍生的甲硅烷基化芳族化合物2-4，可干净地获得ipso脱水产物5-7，而将甲氧基取代的类似物8、9硝化可生成非ipso异构体10、12和11、13受硅空间效应控制。2a，3a和20的顺序ipso-borodesilylation，然后在Pd催化条件下用芳基卤化物处理，构成了原位Suzuki-Miyaura交叉偶联方案，实现了联芳基和杂联芳基23。

  DOI：

  10.1021/ol0506563

文献信息

• Regiocontrolled aerobic oxidative coupling of indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands
  作者：Alison N. Campbell、Eric B. Meyer、Shannon S. Stahl

  DOI：10.1039/c1cc13632a

  日期：——

  Palladium-catalyzed aerobic oxidative cross-couplings of indoles and benzene have been achieved by using 4,5-diazafluorene derivatives as ancillary ligands. Proper choice of the neutral and anionic ligands enables control over the reaction regioselectivity.

  已成功实现以钯为催化剂的吲哚和苯的好氧氧化交叉偶联反应，使用4,5-二氮芴衍生物作为辅助配体。合理选择中性和阴离子配体可以控制反应的区域选择性。
• Directed <i>ortho</i> Metalation-Based Methodology. Halo-, Nitroso-, and Boro-Induced <i>ipso-</i>Desilylation. Link to an <i>in situ</i> Suzuki Reaction
  作者：Zhongdong Zhao、Victor Snieckus

  DOI：10.1021/ol0506563

  日期：2005.6.1

  [reaction: see text] Treatment of DoM-derived silylated aromatics 2-4 under standard electrophilic halogenation conditions cleanly affords ipso-desilyation products 5-7, while nitration of methoxy-substituted analogues 8, 9 leads to non-ipso isomers 10, 12 and 11, 13, controlled by a silicon steric effect. Sequential ipso-borodesilylation of 2a, 3a, and 20 followed by treatment with aryl halides under

  [反应：请参见文本]在标准的亲电子卤化条件下处理DoM衍生的甲硅烷基化芳族化合物2-4，可干净地获得ipso脱水产物5-7，而将甲氧基取代的类似物8、9硝化可生成非ipso异构体10、12和11、13受硅空间效应控制。2a，3a和20的顺序ipso-borodesilylation，然后在Pd催化条件下用芳基卤化物处理，构成了原位Suzuki-Miyaura交叉偶联方案，实现了联芳基和杂联芳基23。
• Anionic Indole <i>N</i>-Carbamoyl N → C Translocation. A Directed remote Metalation Route to 2-Aryl- and 2-Heteroarylindoles. Synthesis of Benz[<i>a</i>]carbazoles and Indeno[1,2-<i>b</i>]indoles
  作者：Zhongdong Zhao、Ashley Jaworski、Isabel Piel、Victor Snieckus

  DOI：10.1021/ol800307g

  日期：2008.7.3

  A new LDA-induced anionic N-C carbamoyl migration of 2-arylindoles (7) is reported. Treatment of N-carbamoylindoles 10 and 13, readily available by direct and ipso-borodesilylative Suzuki-Miyaura cross-coupling routes from 8 and 12, respectively, provides a general route to functionalized 2-arylindoles 11 and 14, respectively (Tables 1 and 2). The reaction has been applied to the synthesis of benzo[a]carbazoles 16 and indeno[1,2-b]indoles 18, and its intramolecularity has been established by a crossover experiment (Scheme 4).