1-(2-bromo-5-benzyloxy)phenyl-2-(4-aminophenyl)ethane | 239445-49-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(2-bromo-5-benzyloxy)phenyl-2-(4-aminophenyl)ethane
• 英文别名: 4-[2-(2-Bromo-5-phenylmethoxyphenyl)ethyl]aniline
• CAS: 239445-49-9
• 化学式: C₂₁H₂₀BrNO
• 分子量: 382.3
• InChiKey: FHWONMSGTKBCHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-bromo-5-benzyloxy)phenyl-2-(4-aminophenyl)ethane 在 硫酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 反应 4.5h， 以84%的产率得到1-(2-bromo-5-benzyloxy)phenyl-2-(4-azidophenyl)ethane
  参考文献：
  名称：

  Intramolecular Cyclizations via Arylnitrenium Ions. Formation of a Six-Membered Ring Rather than a Macrocycle

  摘要：

  The stereochemistry of 1-(3-benzyloxyphenyl)-2-(4-nitrophenyl)ethane has been studied. MMX calculations predicted, and 2D NOESY confirmed, that the bent conformation (global energy minimum) was such that six-membered ring formation, and not macrocyclization, would occur using the corresponding nitrenium ion, and this was found to be the case. Acid-catalyzed decomposition of 1-(3-benzyloxyphenyl)-2-(4-azidophenyl)ethane followed by treatment with (CF3CO)(2)O gave 48% of 2-benzyloxy-6-trifluoroacetamido-9,10-dihydrophenanthrene and 18% of 1-(3-benzyloxyphenyl)-2-(4-trifluoroacetamidophenyl)ethane. Blocking the original point of attack with a bromine atom led to the prediction (MMX, 2D NOESY) that, once again, small ring formation would take place, with macrocyclization possible but less likely. Again, this was found to be so. It is suggested that simple MMX calculations may provide a very rapid, empirical indicator of which precursors would have a readily accessible conformation that could result in intramolecular cyclization leading to macrocycles being preferred over intermolecular reactions.

  DOI：

  10.1021/jo990362t
• 作为产物：
  描述：

  间甲氧基苯甲醇 在 镍 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三甲基氯硅烷 、 copper chromite 、 三溴化硼 、 sodium hydride 、 potassium carbonate 、 一水合肼 、 lithium bromide 作用下， 以 四氢呋喃 、 喹啉 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 59.0h， 生成 1-(2-bromo-5-benzyloxy)phenyl-2-(4-aminophenyl)ethane
  参考文献：
  名称：

  Intramolecular Cyclizations via Arylnitrenium Ions. Formation of a Six-Membered Ring Rather than a Macrocycle

  摘要：

  The stereochemistry of 1-(3-benzyloxyphenyl)-2-(4-nitrophenyl)ethane has been studied. MMX calculations predicted, and 2D NOESY confirmed, that the bent conformation (global energy minimum) was such that six-membered ring formation, and not macrocyclization, would occur using the corresponding nitrenium ion, and this was found to be the case. Acid-catalyzed decomposition of 1-(3-benzyloxyphenyl)-2-(4-azidophenyl)ethane followed by treatment with (CF3CO)(2)O gave 48% of 2-benzyloxy-6-trifluoroacetamido-9,10-dihydrophenanthrene and 18% of 1-(3-benzyloxyphenyl)-2-(4-trifluoroacetamidophenyl)ethane. Blocking the original point of attack with a bromine atom led to the prediction (MMX, 2D NOESY) that, once again, small ring formation would take place, with macrocyclization possible but less likely. Again, this was found to be so. It is suggested that simple MMX calculations may provide a very rapid, empirical indicator of which precursors would have a readily accessible conformation that could result in intramolecular cyclization leading to macrocycles being preferred over intermolecular reactions.

  DOI：

  10.1021/jo990362t