3-(4-tert-butylphenyl)-1-tosyl-1,2,3,5-tetrahydrobenzo[e][1,4]oxazepine | 1616666-48-8

• 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: 3-(4-tert-butylphenyl)-1-tosyl-1,2,3,5-tetrahydrobenzo[e][1,4]oxazepine
• 英文别名: 3-(4-tert-butylphenyl)-1-(4-methylphenyl)sulfonyl-3,5-dihydro-2H-4,1-benzoxazepine
• CAS: 1616666-48-8
• 化学式: C₂₆H₂₉NO₃S
• 分子量: 435.587
• InChiKey: RHIOUGRNUYZFFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-(2-bromobenzyloxy)-2-(4-tert-butylphenyl)ethyl)-4-methylbenzenesulfonamide 在 copper(l) iodide 、 sodium hydride 、 L-脯氨酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以83%的产率得到3-(4-tert-butylphenyl)-1-tosyl-1,2,3,5-tetrahydrobenzo[e][1,4]oxazepine
  参考文献：
  名称：

  Syntheses of Imidazo-, Oxa-, and Thiazepine Ring Systems via Ring-Opening of Aziridines/Cu-Catalyzed C–N/C–C Bond Formation

  摘要：

  A simple and unpredicted synthetic pathway toward racemic and scalemic tetrahydrodibenzoimidazoazepines has been invented serendipitously proceeding through an S(N)2-type ring-opening of N-activated aziridines with 2-bromobenzylamine followed by a hitherto unprecedented cascade cyclization reaction sequence comprising a Cu-catalyzed cross dehydrogenation C-N coupling and an Ullmann C-C bond formation reaction. The tetrahydrobenzoxazepine and the tetrahydrobenzothiazepine derivatives have also been synthesized via the ring-opening of aziridines with 2-bromobenzyl alcohols and -mercaptan, respectively, followed by Cu-catalyzed N-arylation reaction.

  DOI：

  10.1021/jo500888j

文献信息

• Syntheses of Imidazo-, Oxa-, and Thiazepine Ring Systems via Ring-Opening of Aziridines/Cu-Catalyzed C–N/C–C Bond Formation
  作者：Manas K. Ghorai、Ashis Kumar Sahoo、Aditya Bhattacharyya

  DOI：10.1021/jo500888j

  日期：2014.7.18

  A simple and unpredicted synthetic pathway toward racemic and scalemic tetrahydrodibenzoimidazoazepines has been invented serendipitously proceeding through an S(N)2-type ring-opening of N-activated aziridines with 2-bromobenzylamine followed by a hitherto unprecedented cascade cyclization reaction sequence comprising a Cu-catalyzed cross dehydrogenation C-N coupling and an Ullmann C-C bond formation reaction. The tetrahydrobenzoxazepine and the tetrahydrobenzothiazepine derivatives have also been synthesized via the ring-opening of aziridines with 2-bromobenzyl alcohols and -mercaptan, respectively, followed by Cu-catalyzed N-arylation reaction.