ethyl N-{[2-benzoyl-1-(4-methoxyphenyl)-3-oxo-3-phenyl]prop-1-yl}carbamate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: ethyl N-{[2-benzoyl-1-(4-methoxyphenyl)-3-oxo-3-phenyl]prop-1-yl}carbamate
• 英文别名: ethyl N-[2-benzoyl-1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl]carbamate
• 化学式: C₂₆H₂₅NO₅
• 分子量: 431.488
• InChiKey: WETKGAXXUYZMEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl N-{[2-benzoyl-1-(4-methoxyphenyl)-3-oxo-3-phenyl]prop-1-yl}carbamate 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 以66%的产率得到ethyl N-{[1-(4-methoxyphenyl)-3-oxo-3-phenyl]prop-1-yl}carbamate
  参考文献：
  名称：

  Different modes of acid-catalyzed cyclization of 4-(γ-oxoalkyl)semicarbazide hydrazones: 7-membered versus 14-membered cyclic semicarbazones formation

  摘要：

  Acid-catalyzed cyclization of 4-(gamma-oxoalkyl)semicarbazide hydrazones has been studied. 7-Membered cyclic semicarbazones, 2,4,5,6-tetrahydro-3H-1,2,4-triazepin-3-ones, were obtained from the gamma-phenyl-substituted semicarbazides, while the cyclization of the gamma-methyl-substituted semicarbazides involved two molecules of the starting material to result in 14-membered cyclic bis-semicarbazones, 1,2,4,8,9,11-hexaazacyclotetradeca-7,14-diene-3,10-diones. The 4-(gamma-oxoalkyl)semicarbazide hydrazones were prepared according to a four-step synthesis based on amidoallcylation of the sodium enolates of 1,3-diketones with ethyl N-(1-tosylallc-1-yl)carbamates followed by base-promoted retro-Claisen reaction and treatment of the obtained ethyl N-(gamma-oxoalkyl)carbamates with hydrazine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.079
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 32.25h， 生成 ethyl N-{[2-benzoyl-1-(4-methoxyphenyl)-3-oxo-3-phenyl]prop-1-yl}carbamate
  参考文献：
  名称：

  Different modes of acid-catalyzed cyclization of 4-(γ-oxoalkyl)semicarbazide hydrazones: 7-membered versus 14-membered cyclic semicarbazones formation

  摘要：

  Acid-catalyzed cyclization of 4-(gamma-oxoalkyl)semicarbazide hydrazones has been studied. 7-Membered cyclic semicarbazones, 2,4,5,6-tetrahydro-3H-1,2,4-triazepin-3-ones, were obtained from the gamma-phenyl-substituted semicarbazides, while the cyclization of the gamma-methyl-substituted semicarbazides involved two molecules of the starting material to result in 14-membered cyclic bis-semicarbazones, 1,2,4,8,9,11-hexaazacyclotetradeca-7,14-diene-3,10-diones. The 4-(gamma-oxoalkyl)semicarbazide hydrazones were prepared according to a four-step synthesis based on amidoallcylation of the sodium enolates of 1,3-diketones with ethyl N-(1-tosylallc-1-yl)carbamates followed by base-promoted retro-Claisen reaction and treatment of the obtained ethyl N-(gamma-oxoalkyl)carbamates with hydrazine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.079

文献信息

• Different modes of acid-catalyzed cyclization of 4-(γ-oxoalkyl)semicarbazide hydrazones: 7-membered versus 14-membered cyclic semicarbazones formation
  作者：Anastasia A. Fesenko、Anatoly D. Shutalev

  DOI：10.1016/j.tet.2015.10.079

  日期：2015.12

  Acid-catalyzed cyclization of 4-(gamma-oxoalkyl)semicarbazide hydrazones has been studied. 7-Membered cyclic semicarbazones, 2,4,5,6-tetrahydro-3H-1,2,4-triazepin-3-ones, were obtained from the gamma-phenyl-substituted semicarbazides, while the cyclization of the gamma-methyl-substituted semicarbazides involved two molecules of the starting material to result in 14-membered cyclic bis-semicarbazones, 1,2,4,8,9,11-hexaazacyclotetradeca-7,14-diene-3,10-diones. The 4-(gamma-oxoalkyl)semicarbazide hydrazones were prepared according to a four-step synthesis based on amidoallcylation of the sodium enolates of 1,3-diketones with ethyl N-(1-tosylallc-1-yl)carbamates followed by base-promoted retro-Claisen reaction and treatment of the obtained ethyl N-(gamma-oxoalkyl)carbamates with hydrazine. (C) 2015 Elsevier Ltd. All rights reserved.