(R)-3-(2-benzyloxyphenoxy)-1,2-propanediol acetonide | 62703-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-3-(2-benzyloxyphenoxy)-1,2-propanediol acetonide
• 英文别名: (4R)-4-{[2-(Benzyloxy)phenoxy]methyl}-2,2-dimethyl-1,3-dioxolane；(4R)-2,2-dimethyl-4-[(2-phenylmethoxyphenoxy)methyl]-1,3-dioxolane
• CAS: 62703-32-6
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: OGVIQJJLNDUROX-MRXNPFEDSA-N

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：

  (R)-3-(2-benzyloxyphenoxy)-1,2-propanediol acetonide 在 palladium on activated charcoal 盐酸 、 TEA 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 15.0h， 生成 (S)-2-((mesyloxy)methyl)-1,4-benzodioxane
  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
• 作为产物：
  描述：

  2-苯甲氧基苯酚 、 (S)-o-异亚丙基甲磺酸甘油酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (R)-3-(2-benzyloxyphenoxy)-1,2-propanediol acetonide
  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

• Optically active alkylenedioxybenzene derivatives and their use in
  申请人：Mitsubishi Kasei Corporation

  公开号：US05168099A1

  公开（公告）日：1992-12-01

  Optically active alkylenedioxybenzene derivatives of the formula: ##STR1## wherein m is an integer of 2-5, and n is an integer of 1-3, and acid addition salts thereof. A pharmaceutical composition containing a compound (I) or racemate, and a method of treating anxiety in a warm-blooded animal by administering the above compound (I) to said animal are also provided.

  提供了公式为：##STR1##的光学活性的烷基二氧苯衍生物，其中m是2-5的整数，n是1-3的整数，以及其酸盐加成物。还提供了一种含化合物(I)或外消旋体的药物组合物，并通过向该动物投与上述化合物(I)的方法来治疗温血动物的焦虑。
• Drugs Fut. 1997, 22, 225
  作者：

  DOI：——

  日期：——
• J. Med. Chem. 1977, 20, 880-885
  作者：

  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.