spiro<(4-H-1,3-benzodithian)-2,1'-(5'-methoxy-6'-hydroxy-<1H>-2',3'-dihydroindene)>

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: spiro<(4-H-1,3-benzodithian)-2,1'-(5'-methoxy-6'-hydroxy-<1H>-2',3'-dihydroindene)>
• 英文别名: 6-methoxyspiro[1,2-dihydroindene-3,2'-4H-1,3-benzodithiine]-5-ol
• 化学式: C₁₇H₁₆O₂S₂
• 分子量: 316.445
• InChiKey: SYAFZCKINXYMIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-羟基-5-甲氧基-1-茚酮 、 2-(mercaptomethyl)thiophenol 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 spiro<(4-H-1,3-benzodithian)-2,1'-(5'-methoxy-6'-hydroxy-<1H>-2',3'-dihydroindene)>
  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

文献信息

• Sweet Isovanillyl Derivatives:  Synthesis and Structure−Taste Relationships of Conformationally Restricted Analogues
  作者：Anna Arnoldi、Angela Bassoli、Gigliola Borgonovo、Michael G. B. Drew、Lucio Merlini、Gabriella Morini

  DOI：10.1021/jf980246b

  日期：1998.10.1

  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.