2-(3,4-二羟基亚苄基)-3-氧代丁酸乙酯 | 100798-32-1

• 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
• 中文名称: 2-(3,4-二羟基亚苄基)-3-氧代丁酸乙酯
• 英文名称: ethyl 2-(3,4-dihydroxybenzylidene)-3-oxobutanoate
• 英文别名: 2-acetyl-3-(3,4-dihydroxy-phenyl)-acrylic acid ethyl ester；2-Acetyl-3ξ-(3,4-dihydroxy-phenyl)-acrylsaeure-aethylester；2-Acetyl-3-(3,4-dihydroxy-phenyl)-acrylsaeure-aethylester
• CAS: 100798-32-1
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: RMVYAIABVFYIOB-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(3,4-二羟基亚苄基)-3-氧代丁酸乙酯 在 盐酸 、 sodium hydroxide 、 羟胺 作用下， 生成 3-methyl-4-(3,4-dihydroxyphenyl)methylene-isoxazole-5(4H)-one
  参考文献：
  名称：

  Pandya; Pandya, Journal of the Indian Chemical Society, 1957, vol. 34, p. 231,235

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 3,4-二羟基苯甲醛 在 哌啶 作用下， 生成 2-(3,4-二羟基亚苄基)-3-氧代丁酸乙酯
  参考文献：
  名称：

  Pandya; Pandya, Journal of the Indian Chemical Society, 1957, vol. 34, p. 231,235

  摘要：

  DOI：

文献信息

• Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives
  作者：Stancho Stanchev、Georgi Momekov、Frank Jensen、Ilia Manolov

  DOI：10.1016/j.ejmech.2007.05.005

  日期：2008.4

  Six new 4-hydroxycoumarin derivatives have been synthesized. They were characterized by UV-vis, IR, (1)H NMR, (13)C NMR, mass spectral data, elemental analysis, TLC and melting point determination. The new 4-hydroxycoumarin derivatives are studied by computational methods DFT (B3LYP) and force field methods (MM2 and OPLS), in order to optimize their geometry and calculate quantum-chemical properties and conformational analysis. Five new 4-hydroxycoumarin derivatives were tested for cytotoxic activity in two tumor cell lines - HL-60 and EL The obtained results are compared with the utilized anticancer drug melphalan. Two of these compounds - ethyl 2-[(3,4-dihydroxyphenyl)-(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-3-oxobutanoate (SS-16) and ethyl 2-[(4-hydroxy-2-oxo-2H-chromen-3-yl)(3-nitrophenyl)methyl]-3-oxobutanoate (SS-21) show comparatively good cytotoxic properties. Their activity is weaker than melphalan. SS-16 seems to be more active than SS-21. (c) 2007 Elsevier Masson SAS. All rights reserved.