(S)-3-(2-benzyloxyphenoxy)-1,2-propanediol | 119702-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-3-(2-benzyloxyphenoxy)-1,2-propanediol
• 英文别名: (2S)-3-(2-phenylmethoxyphenoxy)propane-1,2-diol
• CAS: 119702-00-0
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: DWFXXPGZPLELIP-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(2-benzyloxyphenoxy)-1,2-propanediol 在 sodium hydroxide 、 palladium on activated charcoal 、 氢溴酸 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 (R)-2-(羟基甲基)-1,4-苯并二噁烷
  参考文献：
  名称：

  （）-和（）-2-羟甲基-1,4-苯并二恶烷的短和对映选择性合成

  摘要：

  描述了由容易获得的手性缩水甘油衍生物制备的（）-和（）-2-羟甲基-1,4-苯并二恶烷的两种简单而高度对映选择性的合成。

  DOI：

  10.1016/s0040-4039(00)82150-4
• 作为产物：
  描述：

  2-苯甲氧基苯酚 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 29.0h， 生成 (S)-3-(2-benzyloxyphenoxy)-1,2-propanediol
  参考文献：
  名称：

  Structure–affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

  摘要：

  A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the alpha(1a)-AR with respect to the other two alpha(1), subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific alpha(1a), affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high alpha(1a) affinity of (S)-1 and its alpha(1a) versus alpha(1b) selectivity slightly increasing the alpha(1a)/alpha(1d) and alpha(1a)/5HT(1A) affinity ratios. The SAR data were evaluated in the light of known alpha(1), subtype pharmacophores and of the alpha(1a)-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.040

文献信息

• DELGADO, ANTONIO;LECLERC, GERARD;LOBATO, CINTA;MAULEON, DAVID, TETRAHEDRON LETT., 29,(1988) N 30, C. 3671-3674
  作者：DELGADO, ANTONIO、LECLERC, GERARD、LOBATO, CINTA、MAULEON, DAVID

  DOI：——

  日期：——
• Structure–affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101
  作者：Cristiano Bolchi、Paolo Catalano、Laura Fumagalli、Marco Gobbi、Marco Pallavicini、Alessandro Pedretti、Luigi Villa、Giulio Vistoli、Ermanno Valoti

  DOI：10.1016/j.bmc.2004.06.040

  日期：2004.9

  A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the alpha(1a)-AR with respect to the other two alpha(1), subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific alpha(1a), affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high alpha(1a) affinity of (S)-1 and its alpha(1a) versus alpha(1b) selectivity slightly increasing the alpha(1a)/alpha(1d) and alpha(1a)/5HT(1A) affinity ratios. The SAR data were evaluated in the light of known alpha(1), subtype pharmacophores and of the alpha(1a)-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models. (C) 2004 Elsevier Ltd. All rights reserved.
• Short and enantioselective syntheses of (R)- and (S)-2-hydroxymethyl-1,4-benzodioxan
  作者：Antonio Delgado、Gerard Leclerc、Ma Cinta Lobato、David Mauleona

  DOI：10.1016/s0040-4039(00)82150-4

  日期：——

  Two straightforward and highly enantioselective syntheses of ()- and ()-2-hydroxymethyl-1,4-benzodioxan from readily available chiral glycidol derivatives are described.

  描述了由容易获得的手性缩水甘油衍生物制备的（）-和（）-2-羟甲基-1,4-苯并二恶烷的两种简单而高度对映选择性的合成。