N-Ethyl-N-(2-bromobenzyl)-1-cyclopentenylamine | 146983-00-8

• 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: N-Ethyl-N-(2-bromobenzyl)-1-cyclopentenylamine
• 英文别名: N-[(2-bromophenyl)methyl]-N-ethylcyclopenten-1-amine
• CAS: 146983-00-8
• 化学式: C₁₄H₁₈BrN
• 分子量: 280.208
• InChiKey: KYLSAURVTWGKPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Ethyl-N-(2-bromobenzyl)-1-cyclopentenylamine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 N-Benzyl-N-cyclopentylethylamine 、 N-Cyclopentyl-N-ethyl-2-bromobenzylamine 、 N-Ethylbenzo-1-azaspiro<4.4>nonane 、 cis-N-Ethyl-4-aza-2,3,3a,4,5,9b-hexahydrobenzindene
  参考文献：
  名称：

  Aryl radical cyclizations onto enamine double bonds

  摘要：

  Aryl radicals from N-alkyl-N-(2-bromobenzyl)-1-cyclohexenylamine 2 and N-alkyl-N-(2-bromobenzyl)-cyclopentenylamine 11 cyclize readily onto the enamine double bond by 6-endo and 5-exo closure. In the case of 2, 6-endo cyclization is the major pathway; however, the 6-endo to 5-exo ratio is dependent upon the N-alkyl substituent. In both cases, the dominant isomer from 6-endo cyclization is the cis isomer. For 2a in toluene, values of k6-endo and k5-exo at 80-degrees-C were 4.6 X 10(8) s-1 and 1.5 x 10(8) s-1, respectively.

  DOI：

  10.1021/jo00060a030
• 作为产物：
  描述：

  2-溴溴苄 在 对甲苯磺酸 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 N-Ethyl-N-(2-bromobenzyl)-1-cyclopentenylamine
  参考文献：
  名称：

  Aryl radical cyclizations onto enamine double bonds

  摘要：

  Aryl radicals from N-alkyl-N-(2-bromobenzyl)-1-cyclohexenylamine 2 and N-alkyl-N-(2-bromobenzyl)-cyclopentenylamine 11 cyclize readily onto the enamine double bond by 6-endo and 5-exo closure. In the case of 2, 6-endo cyclization is the major pathway; however, the 6-endo to 5-exo ratio is dependent upon the N-alkyl substituent. In both cases, the dominant isomer from 6-endo cyclization is the cis isomer. For 2a in toluene, values of k6-endo and k5-exo at 80-degrees-C were 4.6 X 10(8) s-1 and 1.5 x 10(8) s-1, respectively.

  DOI：

  10.1021/jo00060a030