(5S)-5-(2-呋喃基)-3-甲基-1,3-恶唑烷-2-酮 | 769140-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (5S)-5-(2-呋喃基)-3-甲基-1,3-恶唑烷-2-酮
• 英文名称: (5S)-3-methyl-5-(2-furyl)-2-oxazolidinone
• 英文别名: 5S-3-methyl-5-(2-furyl)-2-oxazolidinone；(5S)-5-(furan-2-yl)-3-methyl-1,3-oxazolidin-2-one
• CAS: 769140-93-4
• 化学式: C₈H₉NO₃
• 分子量: 167.164
• InChiKey: BKQZAGYYCYACKB-ZETCQYMHSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  359.4±35.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-乙酰基呋喃 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 (1S,2S)-(+)-N-对甲苯磺酰基-1,2-二苯基乙二胺 N-氯代丁二酰亚胺 、 甲酸 、 氢氟酸 、 potassium tert-butylate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.75h， 生成 (5S)-5-(2-呋喃基)-3-甲基-1,3-恶唑烷-2-酮
  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

文献信息

• [EN] PROCESS TO PRODUCE ENANTIOMERICALLY ENRICHED 1-ARYL- AND 1-HETEROARYL-2-AMINOETHANOLS<br/>[FR] PROCEDE DE PREPARATION D'1-ARYL- ET D'1-HETEROARYL-2-AMINOETHANOLS ENRICHIS EN ENANTIOMERES
  申请人：UPJOHN CO

  公开号：WO2004085414A1

  公开（公告）日：2004-10-07

  The invention relates to a method of preparing enantiomerically enriched amino alcohols of Formula (I) wherein the variable R1, R2, and R3 are defined herein.

  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。
• 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.