(2S)-3-(2'-benzyloxyphenoxy)-1,2-propanediol acetonide | 62501-66-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S)-3-(2'-benzyloxyphenoxy)-1,2-propanediol acetonide
• 英文别名: (S)-3-(2-benzyloxyphenoxy)-1,2-propanediol acetonide；(2R)-3-(2'-Benzyloxyphenoxy)-1,2-propandiol-acetonid；(4S)-4-{[2-(Benzyloxy)phenoxy]methyl}-2,2-dimethyl-1,3-dioxolane；(4S)-2,2-dimethyl-4-[(2-phenylmethoxyphenoxy)methyl]-1,3-dioxolane
• CAS: 62501-66-0
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: OGVIQJJLNDUROX-INIZCTEOSA-N

物化性质

• 熔点：
  36-37 °C
• 沸点：
  420.6±30.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-3-(2'-benzyloxyphenoxy)-1,2-propanediol acetonide 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 、 potassium carbonate 、 一水合肼 作用下， 以 乙二醇甲醚 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (S)-WB-4101
  参考文献：
  名称：

  Ferri; Pallavicini; Piccini, Farmaco, Edizione Scientifica, 1988, vol. 43, # 12 SUPPL., p. 1153 - 1163

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(+)-1,2-异亚丙基甘油 在 吡啶 、 sodium hydride 作用下， 以 乙醇 为溶剂， 生成 (2S)-3-(2'-benzyloxyphenoxy)-1,2-propanediol acetonide
  参考文献：
  名称：

  Ferri; Pallavicini; Piccini, Farmaco, Edizione Scientifica, 1988, vol. 43, # 12 SUPPL., p. 1153 - 1163

  摘要：

  DOI：

文献信息

• 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.
• NELSON W. L.; WENNERSTROM J. E.; DYER D. C.; ENGEL M., J. MED. CHEM. <JMCM-AR>, 1977, 20, NO 7, 880-885
  作者：NELSON W. L.、 WENNERSTROM J. E.、 DYER D. C.、 ENGEL M.

  DOI：——

  日期：——
• Ferri; Pallavicini; Piccini, Farmaco, Edizione Scientifica, 1988, vol. 43, # 12 SUPPL., p. 1153 - 1163
  作者：Ferri、Pallavicini、Piccini、Valoti、Villa

  DOI：——

  日期：——