t-butyl 2-[2-(trimethylstannyl)phenyl]ethylcarbamate | 1382354-89-3

• 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: t-butyl 2-[2-(trimethylstannyl)phenyl]ethylcarbamate
• 英文别名: tert-butyl N-[2-(2-trimethylstannylphenyl)ethyl]carbamate
• CAS: 1382354-89-3
• 化学式: C₁₆H₂₇NO₂Sn
• 分子量: 384.106
• InChiKey: IYDLPZUEARQHRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  t-butyl 2-[2-(trimethylstannyl)phenyl]ethylcarbamate 在 2,2,6,6-四甲基哌啶氧化物 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 1-Boc-吲哚啉
  参考文献：
  名称：

  Approach to the Synthesis of Indoline Derivatives from Diaryliodonium Salts

  摘要：

  An effective method of constructing the indoline moiety via intramolecular nucleophilic ring closure of a diaryliodonium salt is described. Diacetoxyiodoarene compounds (1a-1e) were converted into intermediate Koser's reagent and coupled with arylstannanes (7-10) to form diaryliodonium salts (11a-14e). Indo line compounds with different N-protecting groups, 15, 16, 17, and 18, were synthesized in higher yields by treating salts (11a-14e) with Cs2CO3 and TEMPO. Regardless of the electronic environment of five para-substituted iodoarenes and the natures of four N-protected arylstannane groups, the conversion proceeded well to afford corresponding indolines in yields of 72-84 and 70-84%, respectively.

  DOI：

  10.1021/jo300874m

文献信息

• Approach to the Synthesis of Indoline Derivatives from Diaryliodonium Salts
  作者：Kamalkishor P. Landge、Keun Sam Jang、Sang Yeul Lee、Dae Yoon Chi

  DOI：10.1021/jo300874m

  日期：2012.7.6

  An effective method of constructing the indoline moiety via intramolecular nucleophilic ring closure of a diaryliodonium salt is described. Diacetoxyiodoarene compounds (1a-1e) were converted into intermediate Koser's reagent and coupled with arylstannanes (7-10) to form diaryliodonium salts (11a-14e). Indo line compounds with different N-protecting groups, 15, 16, 17, and 18, were synthesized in higher yields by treating salts (11a-14e) with Cs2CO3 and TEMPO. Regardless of the electronic environment of five para-substituted iodoarenes and the natures of four N-protected arylstannane groups, the conversion proceeded well to afford corresponding indolines in yields of 72-84 and 70-84%, respectively.