2-(4-异丙氧基-3-甲氧基苯基)乙醇 | 1260522-81-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-(4-异丙氧基-3-甲氧基苯基)乙醇
• 英文名称: 2-(4-isopropoxy-3-methoxyphenyl)ethanol
• 英文别名: 2-(3-Methoxy-4-propan-2-yloxyphenyl)ethanol；2-(3-methoxy-4-propan-2-yloxyphenyl)ethanol
• CAS: 1260522-81-3
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: PUTARMMLRPIAFO-UHFFFAOYSA-N

物化性质

• 沸点：
  312.5±27.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-异丙氧基-3-甲氧基苯基)乙醇 在 吡啶 、 咪唑 、 titanium(IV) isopropylate 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 正丁基锂 、 水 、 三氯化硼 、 sodium hydride 、 potassium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 37.0h， 生成 左旋千金藤啶碱
  参考文献：
  名称：

  Total Synthesis of (S)-(-)-Stepholidine Using (S)-tert-Butanesulfinylimine

  摘要：

  A new synthetic strategy of (S)-()-stepholidine, a promising antipsychotic drug candidate, is described. Nucleophilic addition of a laterally lithiated nitrile to a (5)-tert-butanesulfinylimine was used as the key step, which was complished in 94 % de and the main isomer was isolated in 52% yield. (S)-(-)-St epholidine was prepared after another 5 steps, with an overall yield of 18.3% and > 98% ee.

  DOI：

  10.3987/com-10-12056
• 作为产物：
  描述：

  2-(4-异丙氧基-3-甲氧基苯基)乙酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以98%的产率得到2-(4-异丙氧基-3-甲氧基苯基)乙醇
  参考文献：
  名称：

  Total Synthesis of (S)-(-)-Stepholidine Using (S)-tert-Butanesulfinylimine

  摘要：

  A new synthetic strategy of (S)-()-stepholidine, a promising antipsychotic drug candidate, is described. Nucleophilic addition of a laterally lithiated nitrile to a (5)-tert-butanesulfinylimine was used as the key step, which was complished in 94 % de and the main isomer was isolated in 52% yield. (S)-(-)-St epholidine was prepared after another 5 steps, with an overall yield of 18.3% and > 98% ee.

  DOI：

  10.3987/com-10-12056

文献信息

• Synthesis, Resolution, and Biological Evaluation of Atropisomeric (a<i>R</i>)- and (a<i>S</i>)-16-Methyllamellarins N: Unique Effects of the Axial Chirality on the Selectivity of Protein Kinases Inhibition
  作者：Kenyu Yoshida、Ryosuke Itoyama、Masashi Yamahira、Junji Tanaka、Nadège Loaëc、Olivier Lozach、Emilie Durieu、Tsutomu Fukuda、Fumito Ishibashi、Laurent Meijer、Masatomo Iwao

  DOI：10.1021/jm400719y

  日期：2013.9.26

  The total synthesis of the optically active (aR)- and (aS)-16-methyllamellarins N (3a and 3b) was achieved via resolution on HPLC chiral stationary phase. The kinase inhibitory activities of both enantiomers were evaluated on eight protein Icinases relevant to cancer and neurodegenerative diseases (CDKI/cyclin B, CDK2/cyclin A, CDK5/p25, GSK-3 alpha/beta, PIM1, DYRK1A, CLIO, and CK1). Isomer (aR)-3b exhibited potent but nonselective inhibition on all protein kinases except CK1, while (aS)-3a selectively inhibited only GSK-3 alpha/beta, PIM1, and DYRKIA. The different inhibition profiles of (aS)-3a and (aR)-3b were elucidated by docking simulation studies. Although parental lamellarin N (2) inhibited the action of topoisomerase I, both (aS)-3a and (aR)-3b showed no inhibition of this enzyme. The phenotypic scytotoxic activities of 2, (aS)-3a, and (aR)-3b on three cancer cell lines (HeLa, SH-SYSY, and IMR32) changed according to their topoisomerase I and protein kinase inhibitory activities.
• Total Synthesis of (S)-(-)-Stepholidine Using (S)-tert-Butanesulfinylimine
  作者：Yushe Yang、Liqiang Fu、Chenyu Ling

  DOI：10.3987/com-10-12056

  日期：——

  A new synthetic strategy of (S)-()-stepholidine, a promising antipsychotic drug candidate, is described. Nucleophilic addition of a laterally lithiated nitrile to a (5)-tert-butanesulfinylimine was used as the key step, which was complished in 94 % de and the main isomer was isolated in 52% yield. (S)-(-)-St epholidine was prepared after another 5 steps, with an overall yield of 18.3% and > 98% ee.