1-butyl-3,6-dimethyl-3-(2,2,2-trifluoroethyl)indolin-2-one

• 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: 1-butyl-3,6-dimethyl-3-(2,2,2-trifluoroethyl)indolin-2-one
• 英文别名: 1-butyl-3-(2,2,2-trifluoroethyl)-3,6-dimethylindolin-2-one；1-Butyl-3,6-dimethyl-3-(2,2,2-trifluoroethyl)indol-2-one；1-butyl-3,6-dimethyl-3-(2,2,2-trifluoroethyl)indol-2-one
• 化学式: C₁₆H₂₀F₃NO
• 分子量: 299.336
• InChiKey: XQUJZJXGGLQNQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三氟甲烷磺酰氯 、 N-butyl-N-tosylmethacrylamide 在 dipotassium hydrogenphosphate 、 tris(2,2'-bipyridyl)ruthenium dichloride 作用下， 以 乙腈 为溶剂， 以85%的产率得到1-butyl-3,6-dimethyl-3-(2,2,2-trifluoroethyl)indolin-2-one
  参考文献：
  名称：

  Difunctionalization of Alkenes via the Visible-Light-Induced Trifluoromethylarylation/1,4-Aryl Shift/Desulfonylation Cascade Reactions

  摘要：

  A novel visible-light-induced trifluoromethylarylation/1,4-aryl shift/desulfonylation cascade reaction using CF3SO2Cl as CF3 source was described. The protocol provides an efficient approach for the synthesis of alpha-aryl-beta-trifluoromethyl amides and/or CF3-containing oxindoles as well as the isoquinolinediones under benign conditions.

  DOI：

  10.1021/acs.joc.5b00677

文献信息

• Copper-Catalyzed One-Pot Trifluoromethylation/Aryl Migration/Desulfonylation and C(sp²)–N Bond Formation of Conjugated Tosyl Amides
  作者：Wangqing Kong、Maria Casimiro、Estı́baliz Merino、Cristina Nevado

  DOI：10.1021/ja403954g

  日期：2013.10.2

  A novel copper-catalyzed one-pot trifluoromethylation/aryl migration/desulfonylation and C(sp(2))-N bond formation with conjugated tosyl amides as starting materials is presented here. The reaction affords α-aryl-β-trifluoromethyl amides bearing a quaternary stereocenter or trifluoromethylated oxindoles in a regioselective manner.

  此处介绍了一种新型铜催化一锅三氟甲基化/芳基迁移/脱磺酰化和 C(sp(2))-N 键形成，以共轭甲苯磺酰胺为起始材料。该反应以区域选择性方式提供带有季立体中心或三氟甲基化羟吲哚的α-芳基-β-三氟甲基酰胺。
• Metal-Free Direct Intramolecular Carbotrifluoromethylation of Alkenes to Functionalized Trifluoromethyl Azaheterocycles
  作者：Lei Li、Min Deng、Sheng-Cai Zheng、Ya-Ping Xiong、Bin Tan、Xin-Yuan Liu

  DOI：10.1021/ol403391v

  日期：2014.1.17

  The first example of a metal-free direct carbotrifluoromethylation of alkenes using inexpensive TMSCF3 as the CF3 source is described. The methodology not only exhibits high chemoselectivity for this transformation but also expands the substrate scope that is difficult to access by known transition-metal-catalyzed methods.
• Difunctionalization of Alkenes via the Visible-Light-Induced Trifluoromethylarylation/1,4-Aryl Shift/Desulfonylation Cascade Reactions
  作者：Lewei Zheng、Chao Yang、ZhaoZhong Xu、Fei Gao、Wujiong Xia

  DOI：10.1021/acs.joc.5b00677

  日期：2015.6.5

  A novel visible-light-induced trifluoromethylarylation/1,4-aryl shift/desulfonylation cascade reaction using CF3SO2Cl as CF3 source was described. The protocol provides an efficient approach for the synthesis of alpha-aryl-beta-trifluoromethyl amides and/or CF3-containing oxindoles as well as the isoquinolinediones under benign conditions.