3-(4-acetylphenyl)-2-oxazolidinone | 103989-12-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-acetylphenyl)-2-oxazolidinone
• 英文别名: 3-(4-acetylphenyl)oxazolidin-2-one；N-(4-acetylphenyl)oxazolidin-2-one；3-(4-acetyl-phenyl)-oxazolidin-2-one；3-(4-Acetyl-phenyl)-oxazolidin-2-on；N-(p-Acetylphenyl)-2-oxazolidon；3-(4-Acetylphenyl)-1,3-oxazolidin-2-one
• CAS: 103989-12-4
• 化学式: C₁₁H₁₁NO₃
• mdl: MFCD02946492
• 分子量: 205.213
• InChiKey: NKYZULHJSPVQDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-acetylphenyl)-2-oxazolidinone 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 生成 3-(2-(2,4-difluorophenyl)-2-oxoethyl)-5-methyl-5-(4-(2-oxooxazolidin-3-yl)phenyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  Identification and Profiling of Hydantoins—A Novel Class of Potent Antimycobacterial DprE1 Inhibitors

  摘要：

  Tuberculosis is the leading cause of death worldwide from infectious diseases. With the development of drug-resistant strains of Mycobacterium tuberculosis, there is an acute need for new medicines with novel modes of action. Herein, we report the discovery and profiling of a novel hydantoin-based family of antimycobacterial inhibitors of the decaprenylphospho-beta-D-ribofuranose 2-oxidase (DprE1). In this study, we have prepared a library of more than a 100 compounds and evaluated them for their biological and physicochemical properties. The series is characterized by high enzymatic and whole-cell activity, low cytotoxicity, and a good overall physicochemical profile. In addition, we show that the series acts via reversible inhibition of the DprE1 enzyme. Overall, the novel compound family forms an attractive base for progression to further stages of optimization and may provide a promising drug candidate in the future.

  DOI：

  10.1021/acs.jmedchem.8b01356
• 作为产物：
  描述：

  N-(2-羟基乙基)-氨基甲酸乙酯 、 4-碘代苯乙酮 在 copper(l) iodide 、 2,2,6,6-四甲基-3,5-庚二酮 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以93%的产率得到3-(4-acetylphenyl)-2-oxazolidinone
  参考文献：
  名称：

  铜催化氨基醇氨基甲酸酯一锅法合成N-芳基恶唑烷酮

  摘要：

  已经开发出在氨基甲酸酯氨基甲酸酯的有效顺序分子内环化，然后在温和条件下与芳基碘化物进行铜催化的交叉偶联。该反应以高收率进行，并且可以耐受含有官能团（例如腈，酮，醚和卤素）的芳基碘化物。杂芳基碘化物和取代的氨基醇氨基甲酸酯也被很好地耐受。

  DOI：

  10.1021/ol502322c

文献信息

• Synthesis of Oxazolidinones and Derivatives through Three-Component Fixation of Carbon Dioxide
  作者：Congmin Mei、Yibo Zhao、Qianwei Chen、Changsheng Cao、Guangsheng Pang、Yanhui Shi

  DOI：10.1002/cctc.201800142

  日期：2018.7.19

  three‐component fixation of atmospheric CO2 with readily available 1,2‐dichloroethane and aromatic amine toward oxazolidinones catalyzed by in situ NHC was developed. The reaction occurred in good to excellent yields with good generality and wide functional group tolerance, including challenging steric hindered substituted‐dichloroethane (e.g. 1,2‐dichloropropane and 2,3‐dichlorobutane). The catalytic system

  已经开发了一种有效的三组分固定方法，用现成的NHC催化的1,2-二氯乙烷和芳香族胺直接固定在恶唑烷酮上，以固定大气中的CO 2。该反应以良好的通用性和宽泛的官能团耐受性（包括具有挑战性的位阻取代的二氯乙烷（例如1,2-二氯丙烷和2,3-二氯丁烷））以良好的收率获得了良好的收率。该催化体系对空气和湿气不敏感，即使在约0.3atm的二氧化碳压力下也可获得高产率的恶唑烷酮。机理研究表明，该反应是通过NHC-CO 2原位催化NHC催化的加合物中，1-丁基-3-甲基咪唑-2-羧酸盐为中间体，而氨基氯化物参与反应路径。催化剂可以循环使用至少3次而不会明显降低催化活性。该协议还可以有效地制备六元3-芳基-1,3-氧杂嗪酮-2-一，甚至七元3-芳基-1,3-氧杂氮杂-2-酮，当1,3-二氯丙烷和1时使用了4-二氯丁烷。
• A straightforward one-pot synthesis of bioactive N-aryl oxazolidin-2-ones via a highly efficient Fe₃O₄@SiO₂-supported acetate-based butylimidazolium ionic liquid nanocatalyst under metal- and solvent-free conditions
  作者：Radhika Gupta、Manavi Yadav、Rashmi Gaur、Gunjan Arora、Rakesh Kumar Sharma

  DOI：10.1039/c7gc01414g

  日期：——

  A supported ionic liquid-based magnetic nanocatalyst has been fabricated for the formation of pharmaceutically important N-aryl oxazolidin-2-ones.

  已制备一种支持的离子液体基磁性纳米催化剂，用于合成具有药用重要性的N-芳基噁唑烷-2-酮。
• Novel carbapenem compound
  申请人：Sunagawa Makoto

  公开号：US20090029964A1

  公开（公告）日：2009-01-29

  An orally administrable antibacterial agent which contains as an active ingredient a carbapenem compound represented by the formula [1] below, wherein R 0 represents hydrogen atom or the like; R 1 represents C 1 -C 3 alkyl substituted by hydroxyl group or the like; R represents hydrogen atom or a group which regenerates a carboxyl group by hydrolysis in a living body; L represents a single bond, methylene, —OCH 2 (CO)— or the like; and Het represents a group represented by the following formula [2], wherein m and n independently represent 0 or 1; A and B independently represent methylene, carbonyl or the like; Y represents methylene, ethylene, oxygen atom, —OCH 2 —, —NR a CH 2 — (wherein R a represents hydrogen atom, optionally substituted C 1 -C 4 alkyl group or the like) or the like.

  一种口服抗菌剂，其活性成分为由下式[1]表示的碳青霉烯化合物，其中R0表示氢原子或类似物；R1表示C1-C3烷基，该烷基被羟基或类似物取代；R表示氢原子或通过水解在活体内再生羧基的基团；L表示单键，亚甲基，—OCH2（CO）—或类似物；Het表示由下式[2]表示的基团，其中m和n独立地表示0或1；A和B独立地表示亚甲基，羰基或类似物；Y表示亚甲基，乙烯基，氧原子，—OCH2—，—NRaCH2—（其中Ra表示氢原子，可选取代的C1-C4烷基或类似物）或类似物。
• THERAPEUTIC AGENT FOR CHRONIC OBSTRUCTIVE PULMONARY DISEASE
  申请人：Sugasawa Toshinari

  公开号：US20110263550A1

  公开（公告）日：2011-10-27

  Disclosed is a method for the prevention and/or treatment of a chronic obstructive pulmonary disease by administrating a 5-membered cyclic compound represented by the formula below: or a pharmaceutically acceptable salt of the compound or a prodrug of the compound or salt: wherein X represents an oxygen or sulfur atom; R 1 represents a hydrogen atom, a substituted or unsubstituted alkyl or the like; R 2 represents a hydrogen atom, a substituted or unsubstituted alkyl or the like; Y 1 represents single bond, a substituted or unsubstituted alkylene or the like; the wavy line means an (E) or (Z) coordination; R 3 represents a hydrogen atom, a substituted or unsubstituted aryl or the like; Y 2 represents a substituted or unsubstituted alkylene or an alkenylene; R 4 represents a hydrogen atom, a substituted or unsubstituted alkanoyl or the like; and R 5 represents a hydrogen atom or a substituted or unsubstituted alkyl.

  本发明公开了一种通过给予下式所表示的5元环化合物的药物或其盐或其前药的方法预防和/或治疗慢性阻塞性肺疾病：其中X表示氧或硫原子；R1表示氢原子、取代或未取代的烷基或类似物；R2表示氢原子、取代或未取代的烷基或类似物；Y1表示单键、取代或未取代的亚烷基或类似物；波浪线表示（E）或（Z）协调；R3表示氢原子、取代或未取代的芳基或类似物；Y2表示取代或未取代的亚烷基或烯基；R4表示氢原子、取代或未取代的脂肪酰基或类似物；R5表示氢原子或取代或未取代的烷基。
• Therapeutic agent for chronic obstructive pulmonary disease
  申请人：Sugasawa Toshinari

  公开号：US20090131439A1

  公开（公告）日：2009-05-21

  Disclosed is a method for the prevention and/or treatment of a chronic obstructive pulmonary disease by administrating a 5-membered cyclic compound represented by the formula below: or a pharmaceutically acceptable salt of the compound or a prodrug of the compound or salt: wherein X represents an oxygen or sulfur atom; R 1 represents a hydrogen atom, a substituted or unsubstituted alkyl or the like; R 2 represents a hydrogen atom, a substituted or unsubstituted alkyl or the like; Y 1 represents single bond, a substituted or unsubstituted alkylene or the like; the wavy line means an (E) or (Z) coordination; R 3 represents a hydrogen atom, a substituted or unsubstituted aryl or the like; Y 2 represents a substituted or unsubstituted alkylene or an alkenylene; R 4 represents a hydrogen atom, a substituted or unsubstituted alkanoyl or the like; and R 5 represents a hydrogen atom or a substituted or unsubstituted alkyl.

  本发明公开了一种通过给予下式所表示的5元环化合物的药物或其盐或其前药的方法，用于预防和/或治疗慢性阻塞性肺疾病：其中X代表氧或硫原子；R1代表氢原子，取代或未取代的烷基或类似物；R2代表氢原子，取代或未取代的烷基或类似物；Y1代表单键，取代或未取代的亚烷基或类似物；波浪线表示（E）或（Z）配位；R3代表氢原子，取代或未取代的芳基或类似物；Y2代表取代或未取代的亚烷基或烯基；R4代表氢原子，取代或未取代的脂肪酰基或类似物；R5代表氢原子或取代或未取代的烷基。