(R)-N-<3-(4-acetylphenyl)-5-hydroxymethyl-2-oxooxazolidinine> | 121466-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-N-<3-(4-acetylphenyl)-5-hydroxymethyl-2-oxooxazolidinine>
• 英文别名: 5(R)-hydroxymethyl-3-(4-acetylphenyl)-oxazolidin-2-one；(5R)-3-(4-acetylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one
• CAS: 121466-43-1
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: ZAEPGMOWWSWNQU-LLVKDONJSA-N

物化性质

• 沸点：
  425.7±28.0 °C(predicted)
• 密度：
  1.295±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-N-<3-(4-acetylphenyl)-5-hydroxymethyl-2-oxooxazolidinine> 在 盐酸 、 sodium hydroxide 、 sodium azide 、 三乙胺 、 三甲氧基磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 9.5h， 生成 N-[(S)-3-(4-Acetyl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide
  参考文献：
  名称：

  新型抗菌剂dup 721的手性合成

  摘要：

  描述了由4-乙酰基异氰酸酯（）和（R）-丁酸缩水甘油酯（）合成DuP 721 [（S）-N- [3-（4-乙酰苯基）-2-氧代-5-恶唑烷基甲基]乙酰胺]的手性合成方法。。

  DOI：

  10.1016/0040-4020(89)80130-9
• 作为产物：
  描述：

  (R)-<3-(4-acetylphenyl)-2-oxo-5-oxazolidinyl>methyl butyrate 在 sodium methylate 甲醇 作用下， 反应 2.0h， 以95%的产率得到(R)-N-<3-(4-acetylphenyl)-5-hydroxymethyl-2-oxooxazolidinine>
  参考文献：
  名称：

  新型抗菌剂dup 721的手性合成

  摘要：

  描述了由4-乙酰基异氰酸酯（）和（R）-丁酸缩水甘油酯（）合成DuP 721 [（S）-N- [3-（4-乙酰苯基）-2-氧代-5-恶唑烷基甲基]乙酰胺]的手性合成方法。。

  DOI：

  10.1016/0040-4020(89)80130-9

文献信息

• Oxazolidinone compounds and pharmaceutical compositions containing them
  申请人：AstraZeneca AB

  公开号：EP1357122A2

  公开（公告）日：2003-10-29

  The current invention provides an in-vivo hydrolysable ester of a compound of the formula (I) or a pharmaceutically-acceptable salt thereof; wherein X is -O- or -S-; HET is an optionally substituted C-linked 6-membered heteroaryl ring containing 1 or 2 N; Q is Q1 and T is for example:

  当前发明提供了化合物(I)的体内可水解酯或其药用可接受的盐；其中X为-O-或-S-；HET为含有1或2个N的可选择取代的C-连接的6元杂环芳基环；Q为Q1，T为例如：
• Stereocontrolled, Divergent, Al(lll)-Catalyzed Coupling of Chiral <i>N</i>-Aryl Epoxy Amines and CO₂
  作者：Yuseop Lee、Jonghoon Choi、Hyunwoo Kim

  DOI：10.1021/acs.orglett.8b02186

  日期：2018.8.17

  achieved between N-aryl epoxy amines and CO2. By using two different cocatalysts, tetrabutylammonium iodide (TBAI) or 4-dimethylaminopyridine (DMAP) together with an Al(III) Lewis acid, cyclic carbonates or oxazolidinones were selectively produced through two distinct reaction pathways, respectively. The proposed reaction mechanism was supported by the stereochemical determination of the products. A

  N-芳基环氧胺与CO 2之间发生了发散性偶联反应。通过使用两种不同的助催化剂，碘化四丁基铵碘化物（TBAI）或4-二甲基氨基吡啶（DMAP）以及Al（III）Lewis酸，分别通过两种不同的反应途径选择性地生产环状碳酸酯或恶唑烷酮。所提出的反应机理得到产物的立体化学测定的支持。成功实现了克利奈唑胺的克级生产。
• Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group
  作者：Walter A. Gregory、David R. Brittelli、C. L. J. Wang、Mark A. Wuonola、Ronald J. McRipley、David C. Eustice、Virginia S. Eberly、Andrew M. Slee、Martin Forbes、P. T. Bartholomew

  DOI：10.1021/jm00128a003

  日期：1989.8

  The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.
• WANG, CHIA-LIN J.;GREGORY, WALTER A.;WUONOLA, MARK A., TETRAHEDRON , 45,(1989) N, C. 1323-1326
  作者：WANG, CHIA-LIN J.、GREGORY, WALTER A.、WUONOLA, MARK A.

  DOI：——

  日期：——
• OXAZOLIDINONE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：AstraZeneca AB

  公开号：EP1082322A2

  公开（公告）日：2001-03-14