(2-bromophenyl)(2,3-dimethyl-1H-indol-1-yl)methanone | 1370410-30-2

• 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: (2-bromophenyl)(2,3-dimethyl-1H-indol-1-yl)methanone
• 英文别名: N-(2-bromobenzoxyl)-2,3-dimethylindole
• CAS: 1370410-30-2
• 化学式: C₁₇H₁₄BrNO
• 分子量: 328.208
• InChiKey: SGNGVLDYMVCJTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2-bromophenyl)(2,3-dimethyl-1H-indol-1-yl)methanone 在 sodium phosphate dibasic dodecahydrate 、 silver(I) acetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以80%的产率得到10b-methyl-11-methylene-10b,11-dihydro-6H-isoindolo[2,1-a]indol-6-one
  参考文献：
  名称：

  Efficient Construction of Fused Indolines with a 2-Quaternary Center via an Intramolecular Heck Reaction with a Low Catalyst Loading

  摘要：

  An efficient construction of fused indolines with a 2-quaternary center through a palladium-catalyzed intramolecular Heck reaction of N-(2(2-halobenzoxyl)-2,3-disubstituted indoles is disclosed. This protocol provided a straightforward access to diverse fused indolines with good functional group tolerance.

  DOI：

  10.1021/ol300584m
• 作为产物：
  描述：

  2,3-二甲基吲哚 、 2-溴苯甲酰氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2-bromophenyl)(2,3-dimethyl-1H-indol-1-yl)methanone
  参考文献：
  名称：

  Efficient Construction of Fused Indolines with a 2-Quaternary Center via an Intramolecular Heck Reaction with a Low Catalyst Loading

  摘要：

  An efficient construction of fused indolines with a 2-quaternary center through a palladium-catalyzed intramolecular Heck reaction of N-(2(2-halobenzoxyl)-2,3-disubstituted indoles is disclosed. This protocol provided a straightforward access to diverse fused indolines with good functional group tolerance.

  DOI：

  10.1021/ol300584m

文献信息

• CF₃SO₃H-enabled cascade ring-opening/dearomatization of indole derivatives to polycyclic heterocycles
  作者：Zhengdong Yao、Huangdi Feng、Hui Xi、Chuanjun Xi、Weiping Liu

  DOI：10.1039/d1ob00712b

  日期：——

  A novel dearomatization process to produce fused polycyclic indolines via a CF3SO3H-mediated cascade ring-opening of a β-lactam and hydroaminative cyclization is demonstrated. It provides a new strategy for the synthesis of important polycyclic indoline-2-amine derivatives in moderate to excellent yields, as well as with good functional group tolerance. Moreover, transformation of the product was performed

  展示了一种通过CF 3 SO 3 H 介导的 β-内酰胺的级联开环和氢化氨基环化来生产稠合多环二氢吲哚的新型脱芳构化工艺。它为以中等至优异的产率合成重要的多环二氢吲哚-2-胺衍生物提供了一种新策略，并且具有良好的官能团耐受性。此外，对产物进行转化，使相应的酸、醇和酰胺顺利释放。
• Dearomative Indole Bisfunctionalization via a Diastereoselective Palladium-Catalyzed Arylcyanation
  作者：David A. Petrone、Andy Yen、Nicolas Zeidan、Mark Lautens

  DOI：10.1021/acs.orglett.5b02403

  日期：2015.10.2

  The first Pd-catalyzed dearomative indole bisfunctionalization via a diastereoselective arylcyanation is reported. This method facilitates the formation of diverse indoline scaffolds bearing congested stereocenters with high levels of diastereoselectivity. This also represents the first example of a cyanation mechanism involving a 2 benzylic Pd(II) intermediate.