4-formyl-3-methoxy-1,3,5-estratriene | 214754-54-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 4-formyl-3-methoxy-1,3,5-estratriene
• CAS: 214754-54-8
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: ZXBLCBXHARCKNU-HBXLWWENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-formyl-3-methoxy-1,3,5-estratriene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Formic acid (8S,9S,13S,14S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-4-yl ester
  参考文献：
  名称：

  Sweet Isovanillyl Derivatives:  Synthesis and Structure−Taste Relationships of Conformationally Restricted Analogues

  摘要：

  In structure-taste relationships of sweet substances, conformational analysis is important for the definition of the "active conformation" which actually interacts with the sweet taste receptor. This paper describes the synthesis and taste of some isovanillyl derivatives having a rigid structure, which can mimick only one possible conformation of their flexible analogues. We report also the solid state conformation of a sulfur-containing sweet isovanillyl derivative which was established by X-ray analysis. The relationships between conformation and taste were studied by comparison with the current models of the sweet taste receptor and by principal components analysis (PCA) using geometrical descriptors, followed by factor and cluster analysis. A strong correlation was proven between taste and geometry, which is able to explain the taste of rigid derivatives as well as the difference of taste between the two enantiomers of the same compound.

  DOI：

  10.1021/jf980246b
• 作为产物：
  描述：

  3-甲氧基雌甾-1(10),2,4-三烯 、 N,N-二甲基甲酰胺 在 仲丁基锂 作用下， 生成 4-formyl-3-methoxy-1,3,5-estratriene 、 2-formyl-3-methoxy-1,3,5-estratriene
  参考文献：
  名称：

  Sweet Isovanillyl Derivatives:  Synthesis and Structure−Taste Relationships of Conformationally Restricted Analogues

  摘要：

  In structure-taste relationships of sweet substances, conformational analysis is important for the definition of the "active conformation" which actually interacts with the sweet taste receptor. This paper describes the synthesis and taste of some isovanillyl derivatives having a rigid structure, which can mimick only one possible conformation of their flexible analogues. We report also the solid state conformation of a sulfur-containing sweet isovanillyl derivative which was established by X-ray analysis. The relationships between conformation and taste were studied by comparison with the current models of the sweet taste receptor and by principal components analysis (PCA) using geometrical descriptors, followed by factor and cluster analysis. A strong correlation was proven between taste and geometry, which is able to explain the taste of rigid derivatives as well as the difference of taste between the two enantiomers of the same compound.

  DOI：

  10.1021/jf980246b