3-(3-chloro-4-methylphenyl)oxazolidin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-chloro-4-methylphenyl)oxazolidin-2-one
• 英文别名: 3-(3-Chloro-4-methylphenyl)oxazolidin-2-one；3-(3-chloro-4-methylphenyl)-1,3-oxazolidin-2-one
• 化学式: C₁₀H₁₀ClNO₂
• 分子量: 211.648
• InChiKey: NCTITIXAYYPFKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-chloro-4-methylphenyl)oxazolidin-2-one 、 丙烯酸甲酯（MA） 在 silver hexafluoroantimonate 、 (p-cymene)ruthenium(II) chloride 、 氧气 、 copper(II) acetate monohydrate 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 18.0h， 以60%的产率得到
  参考文献：
  名称：

  Ruthenium(II)-Catalyzed C–H Functionalization Using the Oxazolidinone Heterocycle as a Weakly Coordinating Directing Group: Experimental and Computational Insights

  摘要：

  Herein, we report the ruthenium-catalyzed ortho C-H alkenylation of a wide range of N-aryloxazolidinone scaffolds. Alkenylation was achieved with complete mono selectivity with a scope of 27 examples in 2-MeTHF. Yields ranged from 23 to 94%, producing highly decorated oxazolidinone scaffolds. A kinetically relevant C-H cleavage was also observed with a kinetic isotope effect (KIE) of similar to 2. Density functional theory calculations provided information about mechanism, detailing the beta-hydride elimination as the most energetically challenging step of 13.5 kcal mol(-1). In-depth computational kinetic studies also predicted a KIE of 2.17 for C-H cleavage and an intrinsic KIE for the reaction of 2.22, in line with the experimentally observed value.

  DOI：

  10.1021/acscatal.6b01370
• 作为产物：
  描述：

  碳酸乙烯酯 、 3-氯-4-甲基苯胺 在 三乙胺 、 腺嘌呤 作用下， 以 neat (no solvent) 为溶剂， 反应 18.0h， 以74%的产率得到3-(3-chloro-4-methylphenyl)oxazolidin-2-one
  参考文献：
  名称：

  生物催化剂催化的环状碳酸酯和芳香胺合成 N- 芳基-2-恶唑烷酮

  摘要：

  描述了在无溶剂条件下在Et 3 N存在下由生物催化剂腺嘌呤催化的环状碳酸酯和芳基胺合成3-芳基-2-恶唑烷酮的便捷有效方法。该方案适用于多种底物，例如带或不带取代基的环状碳酸酯，以及具有吸电子或供电子基团的芳基胺。即使在位阻情况下，在最佳条件下也能以良好或优异的收率获得产品。研究了反应时间，温度，催化剂用量和原料用量对反应的影响，并探讨了反应机理。

  DOI：

  10.1007/s11164-017-3222-y

文献信息

• Substituted Benzoazepines As Toll-Like Receptor Modulators
  申请人：Howbert James Jeffry

  公开号：US20140066432A1

  公开（公告）日：2014-03-06

  Provided are compositions and methods useful for modulation of signaling through the Toll-like receptors TLR7 and/or TLR8. The compositions and methods have use in treating or preventing disease, including cancer, autoimmune disease, fibrotic disease, cardiovascular disease, infectious disease, inflammatory disorder, graft rejection, or graft-versus-host disease.

  提供的是对调节Toll样受体TLR7和/或TLR8信号传导有用的组合物和方法。这些组合物和方法在治疗或预防疾病方面有用，包括癌症、自身免疫疾病、纤维化疾病、心血管疾病、传染病、炎症性疾病、移植排斥或移植物抗宿主病方面。
• SUBSTITUTED BENZOAZEPINES AS TOLL-LIKE RECEPTOR MODULATORS
  申请人：VentiRx Pharmaceuticals, Inc.

  公开号：EP2663550B1

  公开（公告）日：2016-12-14
• US9718796B2
  申请人：——

  公开号：US9718796B2

  公开（公告）日：2017-08-01
• Ruthenium(II)-Catalyzed C–H Functionalization Using the Oxazolidinone Heterocycle as a Weakly Coordinating Directing Group: Experimental and Computational Insights
  作者：Jamie A. Leitch、Philippe B. Wilson、Claire L. McMullin、Mary F. Mahon、Yunas Bhonoah、Ian H. Williams、Christopher G. Frost

  DOI：10.1021/acscatal.6b01370

  日期：2016.8.5

  Herein, we report the ruthenium-catalyzed ortho C-H alkenylation of a wide range of N-aryloxazolidinone scaffolds. Alkenylation was achieved with complete mono selectivity with a scope of 27 examples in 2-MeTHF. Yields ranged from 23 to 94%, producing highly decorated oxazolidinone scaffolds. A kinetically relevant C-H cleavage was also observed with a kinetic isotope effect (KIE) of similar to 2. Density functional theory calculations provided information about mechanism, detailing the beta-hydride elimination as the most energetically challenging step of 13.5 kcal mol(-1). In-depth computational kinetic studies also predicted a KIE of 2.17 for C-H cleavage and an intrinsic KIE for the reaction of 2.22, in line with the experimentally observed value.
• Synthesis of N-aryl-2-oxazolidinones from cyclic carbonates and aromatic amines catalyzed by bio-catalyst
  作者：Congmin Mei、Yibo Zhao、Ke Zou、Changsheng Cao、Guangsheng Pang、Yanhui Shi

  DOI：10.1007/s11164-017-3222-y

  日期：2018.3

  A convenient and effective method of synthesizing 3-aryl-2-oxazolidinones from cyclic carbonates and aryl amines catalyzed by bio-catalyst adenine in the presence of Et3N under solvent-free conditions is described. The protocol is suitable for the wide scope of substrates, e.g. cyclic carbonates with or without substitutes, and aryl amines with either electron-withdrawing or electron-donating group

  描述了在无溶剂条件下在Et 3 N存在下由生物催化剂腺嘌呤催化的环状碳酸酯和芳基胺合成3-芳基-2-恶唑烷酮的便捷有效方法。该方案适用于多种底物，例如带或不带取代基的环状碳酸酯，以及具有吸电子或供电子基团的芳基胺。即使在位阻情况下，在最佳条件下也能以良好或优异的收率获得产品。研究了反应时间，温度，催化剂用量和原料用量对反应的影响，并探讨了反应机理。