2-(benzyloxy)-4-methyl-1-(prop-1-en-2-yl)benzene | 1242447-18-2

• 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: 2-(benzyloxy)-4-methyl-1-(prop-1-en-2-yl)benzene
• 英文别名: 4-Methyl-2-phenylmethoxy-1-prop-1-en-2-ylbenzene
• CAS: 1242447-18-2
• 化学式: C₁₇H₁₈O
• 分子量: 238.329
• InChiKey: YODCQWCLOKJJBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  2-(benzyloxy)-4-methyl-1-(prop-1-en-2-yl)benzene 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 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：

  2-(2-benzyloxy-4-methylphenyl)-propan-2-ol 在 potassium hydrogensulfate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以96%的产率得到2-(benzyloxy)-4-methyl-1-(prop-1-en-2-yl)benzene
  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

• Dual-Stereocontrol Asymmetric Cobalt-Catalyzed Hydroboration of Sterically Hindered Styrenes
  作者：Heyi Zhang、Zhan Lu

  DOI：10.1021/acscatal.6b02278

  日期：2016.10.7

  An oxazoline aminoisopropylpyridine (OAP) was designed and synthesized for cobalt-catalyzed asymmetric hydroboration of sterically hindered styrenes. A unique dual-stereocontrol phenomenon was observed using a rigid OIP·CoCl2 complex or a flexible OAP with CoCl2 as precatalysts, respectively. The reaction could be easily carried out on a gram scale to afford chiral alkylboronic esters which could be

  设计并合成了恶唑啉氨基异丙基吡啶（OAP），用于钴催化的位阻苯乙烯的不对称硼氢化。分别使用刚性OIP·CoCl 2络合物或以CoCl 2为预催化剂的柔性OAP观察到独特的双重立体控制现象。该反应可以很容易地在克级进行，得到手性烷基硼酸酯，可以将其转化为多种C–X（X = C，N，O）键交叉偶联的产物。在氘实验的基础上，提出了机理上不同的途径。