(3R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylmethoxypropan-1-ol | 656825-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylmethoxypropan-1-ol
• CAS: 656825-40-0
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: QZJFRKWHSWPLNM-KGLIPLIRSA-N

物化性质

• 沸点：
  405.1±35.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylmethoxypropan-1-ol 在 palladium on activated charcoal chromium(VI) oxide 、 camphor-10-sulfonic acid 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 生成 D-(+)-核糖酸-gamma-内酯
  参考文献：
  名称：

  Enantioselective Synthesis and Biological Activity of (3S,4R)- and (3S,4S)-3-Hydroxy-4-hydroxymethyl- 4-butanolides in Relation to PGE₂

  摘要：

  Compounds 9 and 13 were synthesized, and their structures and stereochemistry were elucidated by spectroscopic methods. In competition binding experiments, specific [H-3]-PGE(2) binding was significantly displaced by compound 9 and, to a lesser extent, by 13, in a dose-dependent manner. The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE(2). Compound 9 increases c-fos mRNA level as does PGE2 and antagonizes TPA-induced terminal differentiation.

  DOI：

  10.1021/jm034216y
• 作为产物：
  描述：

  (E)-5-((tert-butyldiphenylsilyl)oxy)pent-2-en-1-ol 在 4 A molecular sieve titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(-)-diethyl tartrate 、 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 72.5h， 生成 (3R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylmethoxypropan-1-ol
  参考文献：
  名称：

  Enantioselective Synthesis and Biological Activity of (3S,4R)- and (3S,4S)-3-Hydroxy-4-hydroxymethyl- 4-butanolides in Relation to PGE₂

  摘要：

  Compounds 9 and 13 were synthesized, and their structures and stereochemistry were elucidated by spectroscopic methods. In competition binding experiments, specific [H-3]-PGE(2) binding was significantly displaced by compound 9 and, to a lesser extent, by 13, in a dose-dependent manner. The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE(2). Compound 9 increases c-fos mRNA level as does PGE2 and antagonizes TPA-induced terminal differentiation.

  DOI：

  10.1021/jm034216y