N-(2-bromoallyl)naphthalene-2-carboxamide | 917092-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-bromoallyl)naphthalene-2-carboxamide
• 英文别名: N-benzyl-N-(2-bromoprop-2-enyl)naphthalene-2-carboxamide
• CAS: 917092-09-2
• 化学式: C₂₁H₁₈BrNO
• 分子量: 380.284
• InChiKey: JOBPNNAKUQUKBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-bromoallyl)naphthalene-2-carboxamide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以10%的产率得到1-Benzyl-4-naphthalen-2-ylpyrrolidin-2-one
  参考文献：
  名称：

  Aryl pyrrolidinones via radical 1,4-aryl migration and 5-endo-trig cyclisation of N-(2-bromoallyl)arylcarboxamides

  摘要：

  Radical reaction of a series of N-(2-bromoallyl)arylearboxamides led to the production of 4-arylpyrrolidin-2-ones and directly reduced materials in comparable yields. A cascade process, involving sequential 5-exo-trig spirocyclisation, beta-scission, and 5-endo-trig cyclisation of the resulting acyl radical, is proposed to explain the pyrrolidinone products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.040
• 作为产物：
  描述：

  2-萘甲酸 在 草酰氯 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-bromoallyl)naphthalene-2-carboxamide
  参考文献：
  名称：

  Aryl pyrrolidinones via radical 1,4-aryl migration and 5-endo-trig cyclisation of N-(2-bromoallyl)arylcarboxamides

  摘要：

  Radical reaction of a series of N-(2-bromoallyl)arylearboxamides led to the production of 4-arylpyrrolidin-2-ones and directly reduced materials in comparable yields. A cascade process, involving sequential 5-exo-trig spirocyclisation, beta-scission, and 5-endo-trig cyclisation of the resulting acyl radical, is proposed to explain the pyrrolidinone products. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.040

文献信息

• Aryl pyrrolidinones via radical 1,4-aryl migration and 5-endo-trig cyclisation of N-(2-bromoallyl)arylcarboxamides
  作者：Matthew J. Palframan、Kirill Tchabanenko、Jeremy Robertson

  DOI：10.1016/j.tetlet.2006.09.040

  日期：2006.11

  Radical reaction of a series of N-(2-bromoallyl)arylearboxamides led to the production of 4-arylpyrrolidin-2-ones and directly reduced materials in comparable yields. A cascade process, involving sequential 5-exo-trig spirocyclisation, beta-scission, and 5-endo-trig cyclisation of the resulting acyl radical, is proposed to explain the pyrrolidinone products. (c) 2006 Elsevier Ltd. All rights reserved.