N-phenyl-1-tosylindolin-3-amine | 1429656-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-phenyl-1-tosylindolin-3-amine
• 英文别名: 1-(4-methylphenyl)sulfonyl-N-phenyl-2,3-dihydroindol-3-amine
• CAS: 1429656-36-9
• 化学式: C₂₁H₂₀N₂O₂S
• 分子量: 364.468
• InChiKey: DWBCCXNICULRAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[2-anilino-2-(2-bromophenyl)ethyl]-4-methylbenzenesulfonamide 在 palladium diacetate 、 potassium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以99%的产率得到N-phenyl-1-tosylindolin-3-amine
  参考文献：
  名称：

  Synthetic Route to Chiral Indolines via Ring-Opening/C–N Cyclization of Activated 2-Haloarylaziridines

  摘要：

  A practical approach for the synthesis of 3-substituted indolines via regio- and stereoselective S(N)2-type ring opening of 2-(2-halophenyl)-N-tosylaziridines with heteroatomic nucleophiles (O, N, and S) followed by palladium catalyzed intramolecular C-N cyclization is reported in excellent yields (up to >99%) and enantiomeric excess (ee 99%)

  DOI：

  10.1021/jo400287a

文献信息

• Iodine-Mediated Electrochemical C(sp²)–H Amination: Switchable Synthesis of Indolines and Indoles
  作者：Kangfei Hu、Yan Zhang、Zhenghong Zhou、Yu Yang、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/acs.orglett.0c01821

  日期：2020.8.7

  A metal-free electrochemical intramolecular C(sp2)–H amination using iodine as a mediator was developed. This method enables a switchable synthesis of indoline and indole derivatives, respectively, from easily available 2-vinyl anilines.

  开发了一种以碘为介质的无金属电化学分子内C（sp 2）–H胺化反应。该方法能够从容易获得的2-乙烯基苯胺分别切换合成吲哚和吲哚衍生物。
• Iodine-catalyzed diamination of styrene in water with the oxidation of H₂O₂
  作者：Liyan Liu、Qi Sun、Zicong Yan、Xinping Liang、Zhenggen Zha、Yu Yang、Zhiyong Wang

  DOI：10.1039/c8gc01332b

  日期：——

  An environmentally friendly diamination was developed in the presence of TMDAI/H2O2 with water as the only by-product. A series of 3-amino indolines can be obtained in good to excellent yields. The reaction conditions are very mild and no any organic solvent or metal was involved in the reaction.

  在TMDAI / H 2 O 2的存在下，以水为唯一副产物，开发了一种环保的渗染方法。可以以优异的产率获得一系列的3-氨基二氢吲哚。反应条件非常温和，反应中不涉及任何有机溶剂或金属。
• 一种水相的烯烃双氨基化合成含氮杂环类化 合物的方法
  申请人：安徽德信佳生物医药有限公司

  公开号：CN108440379B

  公开（公告）日：2021-03-30

  本发明公开了一种水相的烯烃双氨基化合成含氮杂环类化合物的方法，将邻氨基苯乙烯、芳香胺、溶剂和氧化剂加入反应器中，在催化剂的存在下搅拌反应，反应完成后分离提纯，获得含氮杂环类化合物。本发明首次实现了使用低价碘催化剂来催化邻氨基苯乙烯与芳香胺的烯烃双氨基化反应，选择性的生成含氮杂环类化合物。此方法可以使用双氧水等作为氧化剂，可以在纯水中进行反应，是绿色高效的双氨基化方法。
• Alkene Diamination Using Electron-Rich Amines: Hypervalent Iodine-Promoted Inter-/Intramolecular C–N Bond Formation
  作者：Ki Bum Hong、Jeffrey N. Johnston

  DOI：10.1021/ol501693j

  日期：2014.7.18

  A combined inter-/intramolecular oxidative diamination of terminal alkenes is described that uses a hypervalent iodine oxidant and a nucleophilic amine to produce 3-aminoindolines at room temperature. This operationally straightforward and metal-free protocol is compatible with a broad range of functional groups. A mechanism involving the conversion of the amine to an electrophilic nitrogen source is advanced and used to identify a protocol effective with substoichiometric amounts of iodide and commercially available phenyl iodobenzene diacetate (PIDA) as the stoichiometric oxidant.
• Synthetic Route to Chiral Indolines via Ring-Opening/C–N Cyclization of Activated 2-Haloarylaziridines
  作者：Manas K. Ghorai、Y. Nanaji

  DOI：10.1021/jo400287a

  日期：2013.4.19

  A practical approach for the synthesis of 3-substituted indolines via regio- and stereoselective S(N)2-type ring opening of 2-(2-halophenyl)-N-tosylaziridines with heteroatomic nucleophiles (O, N, and S) followed by palladium catalyzed intramolecular C-N cyclization is reported in excellent yields (up to >99%) and enantiomeric excess (ee 99%)