(S)-1-(benzyloxy)-4-bromo-2-(1-bromopropan-2-yl)-5-methylbenzene | 1242447-15-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-1-(benzyloxy)-4-bromo-2-(1-bromopropan-2-yl)-5-methylbenzene
• 英文别名: 1-bromo-5-[(2S)-1-bromopropan-2-yl]-2-methyl-4-phenylmethoxybenzene
• CAS: 1242447-15-9
• 化学式: C₁₇H₁₈Br₂O
• 分子量: 398.137
• InChiKey: QDMWESLMVMOSFX-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1-(benzyloxy)-4-bromo-2-(1-bromopropan-2-yl)-5-methylbenzene 在 aluminum (III) chloride 、 N,N-二乙基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  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
• 作为产物：
  描述：

  (S)-2-(2-(benzyloxy)-4-methylphenyl)propan-1-ol 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(S)-1-(benzyloxy)-4-bromo-2-(1-bromopropan-2-yl)-5-methylbenzene
  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.