(R)-5-(3-羟基苯基)-3-甲基-2-恶唑烷酮 | 110193-49-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: (R)-5-(3-羟基苯基)-3-甲基-2-恶唑烷酮
• 英文名称: (R)-5-(3-hydroxyphenyl)-3-methyl-2-oxazolidone
• 英文别名: (R)-5-(3-Hydroxyphenyl)-3-methyl-2-oxazolidinone；(5R)-5-(3-hydroxyphenyl)-3-methyl-1,3-oxazolidin-2-one
• CAS: 110193-49-2
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: JMKOBHGSFGXCHJ-VIFPVBQESA-N

物化性质

• 溶解度：
  溶于二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-氯甲基-1,3-苯并噻唑 、 (R)-5-(3-羟基苯基)-3-甲基-2-恶唑烷酮 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以27%的产率得到(R)-5-[3-(Benzothiazol-2-ylmethoxy)-phenyl]-3-methyl-oxazolidin-2-one
  参考文献：
  名称：

  Phenylephrine derivatives as leukotriene D4 antagonists

  摘要：

  Two series of phenylephrine derivatives were prepared and tested as inhibitors of leukotriene D4 (LTD4) induced and ovalbumin-induced bronchospasm in the guinea pig. The most potent compound of the urea series, (R)-N,N-diethyl-N-[2-hydroxy-2-[3-(2-quinolinylmethoxy)phenyl]ethyl]-N- methylurea (3, Wy-47,120), was orally active with ED50's of 56 mg/kg vs. LTD4 and 55 mg/kg vs. ovalbumin. When tested as an antagonist of LTD4-induced contraction of isolated guinea pig tracheal strips, 3 was a competitive inhibitor with a p kappa B value of 5.22. In the second series, (R)-3-methyl-5-[3-(2-quinolinylmethoxy)phenyl]-2-oxazolidinone (26, Wy-47,674) had oral ED50's of 36 mg/kg against LTD4 and 95 mg/kg against ovalbumin. Compound 26 selectively antagonized contractile responses of guinea pig trachea evoked by LTD4 (p kappa B = 6.09). In the cat coronary artery, 3 dilated the preparation and blocked the coronary constrictor effect of LTD4. Compound 3 (0.13 mg/kg, iv) also preserved myocardial integrity in rats 48 h after coronary artery ligation. When tested in the rat alcohol-induced gastric lesion model, 3 and 26 manifested a dose-dependent mucosal protection against ethanol.

  DOI：

  10.1021/jm00394a026
• 作为产物：
  描述：

  (R)-2-N-tert-butoxycarbonyl-N-methylamino-1-(3-nitrophenyl)ethanol 在 吡啶 、 盐酸 、 copper acetylacetonate 、 sodium tetrahydroborate 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 17.5h， 生成 (R)-5-(3-羟基苯基)-3-甲基-2-恶唑烷酮
  参考文献：
  名称：

  Whole-cell yeast-mediated preparation of (R)-2-chloro-1-(3-nitrophenyl)ethanol as a synthetic precursor for (R)-phenylephrine

  摘要：

  The incubated whole-cell biocatalyst of Pichia minuta JCM 3622 reduced 2-chloro-1-(3-nitrophenyl)ethanone to provide (R)-2-chloro-1-(3-nitrophenyl)ethanol with 99.2% ee in 87% isolated yield in the presence of Amberlite XAD-7 as a reservoir for the hydrophobic, crystalline and toxic substrate. The product was transformed to (R)-1-(3-hydroxyphenyl)-2-methylaminoethanol (PhenylePhrine,1a), a selective alpha(1)-adrenergic receptor agonist, in 98.0% ee over five steps. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.07.021

文献信息

• MUSSER, JOHN H.;KUBRAK, DENNIS M.;BENDER, REINHOLD H. W.;KREFT, ANTHONY F+, J. MED. CHEM., 30,(1987) N 11, 2087-2093
  作者：MUSSER, JOHN H.、KUBRAK, DENNIS M.、BENDER, REINHOLD H. W.、KREFT, ANTHONY F+

  DOI：——

  日期：——
• Whole-cell yeast-mediated preparation of (R)-2-chloro-1-(3-nitrophenyl)ethanol as a synthetic precursor for (R)-phenylephrine
  作者：Daisuke Tokoshima、Kengo Hanaya、Mitsuru Shoji、Takeshi Sugai

  DOI：10.1016/j.molcatb.2013.07.021

  日期：2013.12

  The incubated whole-cell biocatalyst of Pichia minuta JCM 3622 reduced 2-chloro-1-(3-nitrophenyl)ethanone to provide (R)-2-chloro-1-(3-nitrophenyl)ethanol with 99.2% ee in 87% isolated yield in the presence of Amberlite XAD-7 as a reservoir for the hydrophobic, crystalline and toxic substrate. The product was transformed to (R)-1-(3-hydroxyphenyl)-2-methylaminoethanol (PhenylePhrine,1a), a selective alpha(1)-adrenergic receptor agonist, in 98.0% ee over five steps. (C) 2013 Elsevier B.V. All rights reserved.
• Phenylephrine derivatives as leukotriene D4 antagonists
  作者：John H. Musser、Dennis M. Kubrak、Reinhold H. W. Bender、Anthony F. Kreft、Susan T. Nielsen、Allan M. Lefer、Joseph Chang、Alan J. Lewis、James M. Hand

  DOI：10.1021/jm00394a026

  日期：1987.11

  Two series of phenylephrine derivatives were prepared and tested as inhibitors of leukotriene D4 (LTD4) induced and ovalbumin-induced bronchospasm in the guinea pig. The most potent compound of the urea series, (R)-N,N-diethyl-N-[2-hydroxy-2-[3-(2-quinolinylmethoxy)phenyl]ethyl]-N- methylurea (3, Wy-47,120), was orally active with ED50's of 56 mg/kg vs. LTD4 and 55 mg/kg vs. ovalbumin. When tested as an antagonist of LTD4-induced contraction of isolated guinea pig tracheal strips, 3 was a competitive inhibitor with a p kappa B value of 5.22. In the second series, (R)-3-methyl-5-[3-(2-quinolinylmethoxy)phenyl]-2-oxazolidinone (26, Wy-47,674) had oral ED50's of 36 mg/kg against LTD4 and 95 mg/kg against ovalbumin. Compound 26 selectively antagonized contractile responses of guinea pig trachea evoked by LTD4 (p kappa B = 6.09). In the cat coronary artery, 3 dilated the preparation and blocked the coronary constrictor effect of LTD4. Compound 3 (0.13 mg/kg, iv) also preserved myocardial integrity in rats 48 h after coronary artery ligation. When tested in the rat alcohol-induced gastric lesion model, 3 and 26 manifested a dose-dependent mucosal protection against ethanol.