(R)-2-(2-(benzyloxy)-4-methylphenyl)propane-1,2-diol | 1242447-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-2-(2-(benzyloxy)-4-methylphenyl)propane-1,2-diol
• 英文别名: (2R)-2-(4-methyl-2-phenylmethoxyphenyl)propane-1,2-diol
• CAS: 1242447-19-3
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: VZYVNWYEVXBCSF-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(benzyloxy)-4-methyl-1-(prop-1-en-2-yl)benzene 在 AD-Mix β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 以85%的产率得到(R)-2-(2-(benzyloxy)-4-methylphenyl)propane-1,2-diol
  参考文献：
  名称：

  Total Synthesis and Anticancer Activities of (−)- and (+)-Thespesone

  摘要：

  The natural p-naphthoquinone (-)-thespesone 1 and its (+)-enantiomer were synthesized for the first time by bisacylation of a 5-lithiodihydrobenzofuran 2' with 4-methy1-3-tert-butoxycyclobut-3-ene-1,2-dione 3. The racemate of the required 2-arylpropan-1-ol precursor 10 was kinetically resolved by an enzyme-catalyzed acetylation exclusively of the (S)-enantiomer. Saponification of this acetate mediated by the same enzyme, porcine pancreas lipase (PPL), afforded the (S)-2-arylpropan-1-ol in 96% ee. Its unreacted (R)-enantiomer could be obtained with 77% ee. (-)-(S)-Thespesone was far more efficacious against a panel of six cancer cell lines including multiresistant ones than its (+)-enantiomer and also when compared to thymoquinone, an established natural antitumoral p-quinone from Nigella saliva. Unlike the latter, (-)-thespesone was well tolerated by nonmalignant fibroblasts.

  DOI：

  10.1021/jo1012493

文献信息

• Total Synthesis and Anticancer Activities of (−)- and (+)-Thespesone
  作者：Sandra Breyer、Katharina Effenberger-Neidnicht、Rainer Schobert

  DOI：10.1021/jo1012493

  日期：2010.9.17

  The natural p-naphthoquinone (-)-thespesone 1 and its (+)-enantiomer were synthesized for the first time by bisacylation of a 5-lithiodihydrobenzofuran 2' with 4-methy1-3-tert-butoxycyclobut-3-ene-1,2-dione 3. The racemate of the required 2-arylpropan-1-ol precursor 10 was kinetically resolved by an enzyme-catalyzed acetylation exclusively of the (S)-enantiomer. Saponification of this acetate mediated by the same enzyme, porcine pancreas lipase (PPL), afforded the (S)-2-arylpropan-1-ol in 96% ee. Its unreacted (R)-enantiomer could be obtained with 77% ee. (-)-(S)-Thespesone was far more efficacious against a panel of six cancer cell lines including multiresistant ones than its (+)-enantiomer and also when compared to thymoquinone, an established natural antitumoral p-quinone from Nigella saliva. Unlike the latter, (-)-thespesone was well tolerated by nonmalignant fibroblasts.