(S)-1-(2-furyl)-2-(methylamino)ethanol | 769140-94-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-1-(2-furyl)-2-(methylamino)ethanol
• 英文别名: N-methyl S-1-(2-furyl)-2-aminoethanol；(1S)-1-(furan-2-yl)-2-(methylamino)ethanol
• CAS: 769140-94-5
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: PLZGRWOGYMZWLZ-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-furyl)-2-(methylamino)ethanol 、 N-(4-chlorobenzyl)-9-(chloromethyl)-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamide 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-[(4-chlorophenyl)methyl]-7-[[[(2S)-2-(furan-2-yl)-2-hydroxyethyl]-methylamino]methyl]-4-methyl-3,10-dioxo-1,4-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13),11-tetraene-11-carboxamide
  参考文献：
  名称：

  The design and development of 2-aryl-2-hydroxy ethylamine substituted 1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamides as inhibitors of human cytomegalovirus polymerase

  摘要：

  Discovery efforts were focused on identifying a non-nucleoside antiviral for treating infections caused by human cytomegalovirus (HCMV) with equal or better potency and diminished toxicity compared to current therapeutics. This Letter describes the HCMV DNA polymerase inhibition and in vitro antiviral activity of various 2-aryl-2-hydroxy ethylamine substituted 1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxamides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.094
• 作为产物：
  描述：

  (5S)-5-(2-呋喃基)-3-甲基-1,3-恶唑烷-2-酮 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 3.0h， 以98%的产率得到(S)-1-(2-furyl)-2-(methylamino)ethanol
  参考文献：
  名称：

  [EN] PROCESS TO PRODUCE ENANTIOMERICALLY ENRICHED 1-ARYL- AND 1-HETEROARYL-2-AMINOETHANOLS
  [FR] PROCEDE DE PREPARATION D'1-ARYL- ET D'1-HETEROARYL-2-AMINOETHANOLS ENRICHIS EN ENANTIOMERES

  摘要：

  这项发明涉及一种制备式(I)的对映体富集氨基醇的方法，其中变量R1、R2和R3在此处被定义。

  公开号：

  WO2004085414A1

文献信息

• Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols
  作者：Steven P. Tanis、Bruce R. Evans、James A. Nieman、Timothy T. Parker、Wendy D. Taylor、Steven E. Heasley、Paul M. Herrinton、William R. Perrault、Richard A. Hohler、Lester A. Dolak、Matthew R. Hester、Eric P. Seest

  DOI：10.1016/j.tetasy.2006.07.017

  日期：2006.8

  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.