Methyl-carbamic acid (S)-2-chloro-1-pyridin-3-yl-ethyl ester | 913289-33-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Methyl-carbamic acid (S)-2-chloro-1-pyridin-3-yl-ethyl ester
• CAS: 913289-33-5
• 化学式: C₉H₁₁ClN₂O₂
• 分子量: 214.652
• InChiKey: OFEIUFZASFXEOL-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Methyl-carbamic acid (S)-2-chloro-1-pyridin-3-yl-ethyl ester 在 氢氧化钾 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.25h， 生成 (S)-1-(3-pyridyl)-2-(methylamino)ethanol
  参考文献：
  名称：

  Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols

  摘要：

  As part of medicinal chemistry efforts we found it necessary to develop general syntheses of highly enantiomerically enriched 1-aryl-2-chloroethanols and 1-aryl-2-methylaminoethanols. A survey of literature methods suggested that a truly general approach had not yet been reported, encouraging us to undertake the development of such a methodology. This study describes the design, development, and reduction to practice of a general synthesis of chiral 1-aryl-2-chloroethanols and the transformation of these entities to highly enantiomerically enriched 1-aryl-2-methylaminoethanols. Of particular importance were observations of the impact of solvent and the method of catalyst preparation on the yield and enantiomerical excess of chlorohydrins prepared via Noyori transfer hydrogenations of aryl-chloromethyl ketones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.017
• 作为产物：
  描述：

  2-氯-1-(吡啶-3-基)乙酮 在 RuCl[(1R,2R)-p-TsNCH(Ph)-CH(Ph)NH2](η⁶-p-cymene) 甲酸 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、4.0 kPa 条件下， 反应 0.75h， 生成 Methyl-carbamic acid (S)-2-chloro-1-pyridin-3-yl-ethyl ester
  参考文献：
  名称：

  Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols

  摘要：

  As part of medicinal chemistry efforts we found it necessary to develop general syntheses of highly enantiomerically enriched 1-aryl-2-chloroethanols and 1-aryl-2-methylaminoethanols. A survey of literature methods suggested that a truly general approach had not yet been reported, encouraging us to undertake the development of such a methodology. This study describes the design, development, and reduction to practice of a general synthesis of chiral 1-aryl-2-chloroethanols and the transformation of these entities to highly enantiomerically enriched 1-aryl-2-methylaminoethanols. Of particular importance were observations of the impact of solvent and the method of catalyst preparation on the yield and enantiomerical excess of chlorohydrins prepared via Noyori transfer hydrogenations of aryl-chloromethyl ketones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.017