(R)-3-(dimethylamino)butan-1-ol | 914461-77-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-3-(dimethylamino)butan-1-ol
• 英文别名: (R)-3-dimethylamino-butan-1-ol；(3R)-3-(dimethylamino)butan-1-ol
• CAS: 914461-77-1
• 化学式: C₆H₁₅NO
• 分子量: 117.191
• InChiKey: QTTKJYGPXLCJNF-ZCFIWIBFSA-N

物化性质

• 沸点：
  169.7±13.0 °C(Predicted)
• 密度：
  0.883±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-(dimethylamino)butan-1-ol 、 4-氟-2-甲基苯酚 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以34%的产率得到(R)-4-(4-fluoro-2-methylphenoxy)-N,N-dimethylbutan-2-amine
  参考文献：
  名称：

  Expanding the medicinal chemistry toolbox: stereospecific generation of methyl group-containing propylene linkers

  摘要：

  Use of alkyl substituted propylene linkers as a strategy for fine-tuning the biological activity of medicinal agents requires ready access to these substrates. Herein, a general strategy is described for stereo specifically generating 18 chiral mono- and di-methylpropylene linkers. All twelve vicinal 1,2-propylene targets were generated from methyl-3-hydroxybutanoate and all 1,3-disubstituted targets from pentane-2,4-diol. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.020
• 作为产物：
  描述：

  (R)-tert-butyl 4-hydroxybutan-2-yl(methyl)carbamate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以100%的产率得到(R)-3-(dimethylamino)butan-1-ol
  参考文献：
  名称：

  Expanding the medicinal chemistry toolbox: stereospecific generation of methyl group-containing propylene linkers

  摘要：

  Use of alkyl substituted propylene linkers as a strategy for fine-tuning the biological activity of medicinal agents requires ready access to these substrates. Herein, a general strategy is described for stereo specifically generating 18 chiral mono- and di-methylpropylene linkers. All twelve vicinal 1,2-propylene targets were generated from methyl-3-hydroxybutanoate and all 1,3-disubstituted targets from pentane-2,4-diol. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.020

文献信息

• Novel Acetylcholine and Carbamoylcholine Analogues: Development of a Functionally Selective α₄β₂ Nicotinic Acetylcholine Receptor Agonist
  作者：Camilla P. Hansen、Anders A. Jensen、Jeppe K. Christensen、Thomas Balle、Tommy Liljefors、Bente Frølund

  DOI：10.1021/jm701625v

  日期：2008.12.11

  A series of carbamoylcholine and acetylcholine analogues were synthesized and characterized pharmacologically at neuronal nicotinic acetylcholine receptors (nAChRs). Several of the compounds displayed low nanomolar binding affinities to the alpha(4)beta(2) nAChR and pronounced selectivity for this subtype over alpha(3)beta(4), alpha(4)beta(4), and alpha(7) nAChRs. The high nAChR activity of carbamoylcholine analogue 5d was found to reside in its R-enantiomer, a characteristic most likely true for all other compounds in the series. Interestingly, the pronounced alpha(4)beta(2) selectivities exhibited by some of the compounds in the binding assays translated into functional selectivity. Compound 5a was a fairly potent partial alpha(4)beta(2) nAChR agonist with negligible activities at the alpha(3)beta(4) and alpha(7) subtypes, thus being one of the few truly functionally selective alpha(4)beta(2) nAChR agonists published to date. Ligand-protein docking experiments using homology models of the amino-terminal domains of alpha(4)beta(2) and alpha(3)beta(4) nAChRs identified residues Val 111(beta(2))/Ile 113(beta(4)), Phe 119(beta(2))/Gln 121(beta(4)), and Thr155(alpha(4))/Ser 150(alpha(3)) as possible key determinants of the alpha(4)beta(2)/alpha(3)beta(4)-selectivity displayed by the analogues. 4
• Expanding the medicinal chemistry toolbox: stereospecific generation of methyl group-containing propylene linkers
  作者：Kristopher Bosse、Jason Marineau、Deane M. Nason、Anton J. Fliri、Barb E. Segelstein、Kishor Desai、Robert A. Volkmann

  DOI：10.1016/j.tetlet.2006.08.020

  日期：2006.10

  Use of alkyl substituted propylene linkers as a strategy for fine-tuning the biological activity of medicinal agents requires ready access to these substrates. Herein, a general strategy is described for stereo specifically generating 18 chiral mono- and di-methylpropylene linkers. All twelve vicinal 1,2-propylene targets were generated from methyl-3-hydroxybutanoate and all 1,3-disubstituted targets from pentane-2,4-diol. (c) 2006 Elsevier Ltd. All rights reserved.