tert-butyl N-[(2-bromo-5-methoxyphenyl)methyl]-N-(2-methylprop-2-enoyl)carbamate | 1144029-12-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl N-[(2-bromo-5-methoxyphenyl)methyl]-N-(2-methylprop-2-enoyl)carbamate
• CAS: 1144029-12-8
• 化学式: C₁₇H₂₂BrNO₄
• 分子量: 384.27
• InChiKey: YLEYPFMWWKBNRM-UHFFFAOYSA-N

物化性质

• 沸点：
  444.7±55.0 °C(predicted)
• 密度：
  1.292±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2-bromo-5-methoxyphenyl)methyl]-N-(2-methylprop-2-enoyl)carbamate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以29%的产率得到tert-butyl 8-methoxy-4-methyl-3-oxo-4,5-dihydro-1H-2-benzazepine-2-carboxylate
  参考文献：
  名称：

  Mechanistic study of 7-endo selective radical cyclization of the aryl radical

  摘要：

  Mechanistic studies on the novel 7-endo selective radical cyclization were carried out. The reaction afforded three products, 7-endo product, 6-exo product, and reduced product. The distribution of these products was estimated by GC analyses. The 7-endo/6-exo selectivity was almost constant against variation in the concentration of Bu3SnH, while the reduction/cyclization ratio was sensitive to the concentration of Bu3SnH. The reduction/cyclization ratio was mainly affected by the rotational isomeric ratio of the cyclization precursor. Kinetic analyses indicated that the cyclization process should be irreversible, and the rate constant of 7-endo/6-exo radical cyclization was estimated to be about 3.3 x 10(8) s (1) at 80 degrees C. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.132
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 N-(2-bromo-5-methoxybenzyl)methacrylamide 以99%的产率得到tert-butyl N-[(2-bromo-5-methoxyphenyl)methyl]-N-(2-methylprop-2-enoyl)carbamate
  参考文献：
  名称：

  An efficient preparation of N-alkyl-2-benzazepine derivatives and investigation of their biological activity

  摘要：

  N-Alkyl-2-benzazepine derivatives are readily prepared through N-alkylation of secondary 2-benzazepines that are constructed via 7-endo selective cyclization of radical cyclization of N-boc-N-(2-bromo5-methoxyphenylmethyl) methacrylamides. The structure and activity relationship of these derivatives are examined. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.117

文献信息

• An efficient preparation of N-alkyl-2-benzazepine derivatives and investigation of their biological activity
  作者：Akio Kamimura、Masahiro So、Tomohiro Kuratani、Kenji Matsuura、Makoto Inui

  DOI：10.1016/j.bmcl.2009.04.117

  日期：2009.6

  N-Alkyl-2-benzazepine derivatives are readily prepared through N-alkylation of secondary 2-benzazepines that are constructed via 7-endo selective cyclization of radical cyclization of N-boc-N-(2-bromo5-methoxyphenylmethyl) methacrylamides. The structure and activity relationship of these derivatives are examined. (C) 2009 Elsevier Ltd. All rights reserved.
• Mechanistic study of 7-endo selective radical cyclization of the aryl radical
  作者：Akio Kamimura、Yuriko Ishihara、Masahiro So、Takahiro Hayashi

  DOI：10.1016/j.tetlet.2009.01.132

  日期：2009.4

  Mechanistic studies on the novel 7-endo selective radical cyclization were carried out. The reaction afforded three products, 7-endo product, 6-exo product, and reduced product. The distribution of these products was estimated by GC analyses. The 7-endo/6-exo selectivity was almost constant against variation in the concentration of Bu3SnH, while the reduction/cyclization ratio was sensitive to the concentration of Bu3SnH. The reduction/cyclization ratio was mainly affected by the rotational isomeric ratio of the cyclization precursor. Kinetic analyses indicated that the cyclization process should be irreversible, and the rate constant of 7-endo/6-exo radical cyclization was estimated to be about 3.3 x 10(8) s (1) at 80 degrees C. (C) 2009 Elsevier Ltd. All rights reserved.