3-benzylamino-2-methylbutan-2-ol | 63557-73-3

• 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: 3-benzylamino-2-methylbutan-2-ol
• 英文别名: N-Benzylamino-2-methylbutan-2-ol；(β-Oxy-α-methyl-isobutyl)-benzylamin；3-(Benzylamino)-2-methylbutan-2-ol
• CAS: 63557-73-3
• 化学式: C₁₂H₁₉NO
• mdl: MFCD21106820
• 分子量: 193.289
• InChiKey: SZZRCZNJFYKEAT-UHFFFAOYSA-N

物化性质

• 沸点：
  310.1±17.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzylamino-2-methylbutan-2-ol 在 锂硼氢 、 三甲基氯硅烷 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 生成
  参考文献：
  名称：

  Discovery of novel 2-(alkylmorpholin-4-yl)-6-(3-fluoropyridin-4-yl)-pyrimidin-4(3H)-ones as orally-active GSK-3β inhibitors for Alzheimer’s disease

  摘要：

  We herein describe the results of further evolution of GSK-3 beta inhibitors for Alzheimer's disease from our promising compounds with in vivo tau phosphorylation inhibitory activity by oral administration. Introduction of a low alkyl group instead of the phenyl group at the 3-position of the morpholine moiety aiming to improve pharmacokinetic profiles resulted in potent low molecular weight GSK-3 beta inhibitors with good in vitro pharmacokinetic profiles, which also showed in vivo tau phosphorylation inhibitory activity by oral administration. Effect of the stereochemistry of the alkyl moiety is also discussed using docking models. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.01.005
• 作为产物：
  描述：

  2,3-环氧-2-甲基丁烷 、 苄胺 生成 3-benzylamino-2-methylbutan-2-ol
  参考文献：
  名称：

  Gabel, Ukrains'kii Khemichnii Zhurnal, 1926, vol. 2, p. 382

  摘要：

  DOI：

文献信息

• Regioselectivity in a Highly Efficient, Microwave-Assisted Epoxide Aminolysis
  作者：Harriet Lindsay、Hinal Desai、Brendan D’Souza、Devin Foether、Benjamin Johnson

  DOI：10.1055/s-2007-965927

  日期：2007.3

  We have developed a microwave-assisted aminolysis of epoxides as an efficient method for synthesizing a number of β-amino alcohols. In most cases, including in reactions of amines with a trisubstituted epoxide, only one equivalent of amine is required to obtain good yields. The reactions are consistently regioselective for amine nucleophiles of varying strengths and for both hindered and unhindered epoxides. In some cases, this regioselectivity could be enhanced by using a polar aprotic or a non-polar solvent.

  我们开发了一种微波辅助的环氧化物胺解法作为合成多种β-氨基醇的有效方法。在大多数情况下，包括三取代环氧化物与胺的反应，只需使用一个当量的胺即可获得良好的产率。这些反应对于不同强度的胺亲核试剂以及阻碍性和非阻碍性的环氧化物都表现出一致的区域选择性。在某些情况下，可以通过使用极性非质子溶剂或非极性溶剂来增强这种区域选择性。
• Burfield,D.R. et al., Journal of the Chemical Society. Perkin transactions I, 1977, p. 666 - 671
  作者：Burfield,D.R. et al.

  DOI：——

  日期：——
• Gabel, Ukrains'kii Khemichnii Zhurnal, 1926, vol. 2, p. 382
  作者：Gabel

  DOI：——

  日期：——
• Discovery of novel 2-(alkylmorpholin-4-yl)-6-(3-fluoropyridin-4-yl)-pyrimidin-4(3H)-ones as orally-active GSK-3β inhibitors for Alzheimer’s disease
  作者：Kenji Fukunaga、Daiki Sakai、Kazutoshi Watanabe、Kazuki Nakayama、Toshiyuki Kohara、Hiroshi Tanaka、Shinji Sunada、Mika Nabeno、Masako Okamoto、Ken-Ichi Saito、Jun-ichi Eguchi、Akiko Mori、Shinji Tanaka、Keiko Inazawa、Takashi Horikawa

  DOI：10.1016/j.bmcl.2015.01.005

  日期：2015.3

  We herein describe the results of further evolution of GSK-3 beta inhibitors for Alzheimer's disease from our promising compounds with in vivo tau phosphorylation inhibitory activity by oral administration. Introduction of a low alkyl group instead of the phenyl group at the 3-position of the morpholine moiety aiming to improve pharmacokinetic profiles resulted in potent low molecular weight GSK-3 beta inhibitors with good in vitro pharmacokinetic profiles, which also showed in vivo tau phosphorylation inhibitory activity by oral administration. Effect of the stereochemistry of the alkyl moiety is also discussed using docking models. (C) 2015 Elsevier Ltd. All rights reserved.