(E)-ethyl 4-(5-(benzyloxy)-2-bromo-4-methoxyphenyl)but-2-enoate | 1432493-94-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-ethyl 4-(5-(benzyloxy)-2-bromo-4-methoxyphenyl)but-2-enoate
• 英文别名: ethyl (E)-4-(2-bromo-4-methoxy-5-phenylmethoxyphenyl)but-2-enoate
• CAS: 1432493-94-1
• 化学式: C₂₀H₂₁BrO₄
• 分子量: 405.288
• InChiKey: PRYGSHXLCZFNLY-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 4-(5-(benzyloxy)-2-bromo-4-methoxyphenyl)but-2-enoate 、 copper(l) cyanide 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以76%的产率得到ethyl 1-amino-6-(benzyloxy)-7-methoxynaphthalene-2-carboxylate
  参考文献：
  名称：

  CuCN-Mediated Cascade Cyclization of 4-(2-Bromophenyl)-2-butenoates: A High-Yield Synthesis of Substituted Naphthalene Amino Esters

  摘要：

  A new method of CuCN-mediated one-pot cyclization of 4-(2-bromophenyl)-2-butenoates leading to efficient synthesis of substituted naphthalene amino esters including phenanthrene aromatic structural units is described. Deuterium labeling studies establish that this one-pot cascade cyclization proceeds through isomerization of olefin, intramolecular C-C bond cyclization, and aromatization as the key intermediates, all occurring in a single step.

  DOI：

  10.1021/jo400244h
• 作为产物：
  描述：

  5-benzyloxy-2-bromo-4,β-dimethoxystyrene 在 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (E)-ethyl 4-(5-(benzyloxy)-2-bromo-4-methoxyphenyl)but-2-enoate
  参考文献：
  名称：

  CuCN-Mediated Cascade Cyclization of 4-(2-Bromophenyl)-2-butenoates: A High-Yield Synthesis of Substituted Naphthalene Amino Esters

  摘要：

  A new method of CuCN-mediated one-pot cyclization of 4-(2-bromophenyl)-2-butenoates leading to efficient synthesis of substituted naphthalene amino esters including phenanthrene aromatic structural units is described. Deuterium labeling studies establish that this one-pot cascade cyclization proceeds through isomerization of olefin, intramolecular C-C bond cyclization, and aromatization as the key intermediates, all occurring in a single step.

  DOI：

  10.1021/jo400244h

文献信息

• CuCN-Mediated Cascade Cyclization of 4-(2-Bromophenyl)-2-butenoates: A High-Yield Synthesis of Substituted Naphthalene Amino Esters
  作者：R. Santhosh Reddy、Pragati K Prasad、Brij Bhushan Ahuja、Arumugam Sudalai

  DOI：10.1021/jo400244h

  日期：2013.5.17

  A new method of CuCN-mediated one-pot cyclization of 4-(2-bromophenyl)-2-butenoates leading to efficient synthesis of substituted naphthalene amino esters including phenanthrene aromatic structural units is described. Deuterium labeling studies establish that this one-pot cascade cyclization proceeds through isomerization of olefin, intramolecular C-C bond cyclization, and aromatization as the key intermediates, all occurring in a single step.