ethyl (2E)-3-[(ethoxycarbonyl)amino]-2-nitro-3-phenylprop-2-enoate | 1448589-69-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (2E)-3-[(ethoxycarbonyl)amino]-2-nitro-3-phenylprop-2-enoate
• 英文别名: ethyl (E)-3-(ethoxycarbonylamino)-2-nitro-3-phenylprop-2-enoate
• CAS: 1448589-69-2
• 化学式: C₁₄H₁₆N₂O₆
• 分子量: 308.291
• InChiKey: BEDQHCJLENJYHR-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl α-nitrocinnamate 、 ethyl N-{[(4-nitrobenzene)sulfonyl]oxy}carbamate 在 calcium oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以66.5 mg的产率得到ethyl (2E)-3-[(ethoxycarbonyl)amino]-2-nitro-3-phenylprop-2-enoate
  参考文献：
  名称：

  Selective Amination Reactions of α-Nitro Aryl and Heteroaryl Enoates

  摘要：

  Highly functionalized tetrasubstituted alkenes were obtained by an unexpected amination reaction promoted by ethyl nosyloxycarbamate on various alpha-nitro aryl and heteroaryl enoates. A nitrene is likely the aminating species responsible for the observed insertion reaction leading to (E)-beta-amino alpha-nitro enoates as the major products, regardless of the substrate configuration. The compounds, bearing two nitrogenous functional groups in different oxidation states, can be regarded as interesting synthons. In contrast, aziridination was observed for alpha-nitro alkyl enoates or beta-nitro allylic alcohols.

  DOI：

  10.1021/jo4012859

文献信息

• Selective Amination Reactions of α-Nitro Aryl and Heteroaryl Enoates
  作者：Stefania Fioravanti、Lucio Pellacani、Maria Cecilia Vergari

  DOI：10.1021/jo4012859

  日期：2013.8.16

  Highly functionalized tetrasubstituted alkenes were obtained by an unexpected amination reaction promoted by ethyl nosyloxycarbamate on various alpha-nitro aryl and heteroaryl enoates. A nitrene is likely the aminating species responsible for the observed insertion reaction leading to (E)-beta-amino alpha-nitro enoates as the major products, regardless of the substrate configuration. The compounds, bearing two nitrogenous functional groups in different oxidation states, can be regarded as interesting synthons. In contrast, aziridination was observed for alpha-nitro alkyl enoates or beta-nitro allylic alcohols.