3-(2-氯苯基)-恶唑烷-2-酮 | 101869-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(2-氯苯基)-恶唑烷-2-酮
• 英文名称: 3-(2-chlorophenyl)-oxazolidin-2-one
• 英文别名: 3-(2-chlorophenyl)oxazolidin-2-one；3-(2-Chloro-phenyl)-oxazolidin-2-one；3-(2-chlorophenyl)-1,3-oxazolidin-2-one
• CAS: 101869-85-6
• 化学式: C₉H₈ClNO₂
• 分子量: 197.621
• InChiKey: ZZKLNCOXKZXRMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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-(2-氯苯基)-恶唑烷-2-酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-[(2-氯苯基)氨基]-乙醇
  参考文献：
  名称：

  Bis-aryl Urea Derivatives as Potent and Selective LIM Kinase (Limk) Inhibitors

  摘要：

  The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 < 25 nM), excellent selectivity against ROCK and JNK kinases (>400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 < 1 mu M), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 mu M inhibited only Limk1 and STK16 with >= 80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.

  DOI：

  10.1021/jm501680m
• 作为产物：
  描述：

  邻氯苯胺 在 sodium hydroxide 、 苯 作用下， 生成 3-(2-氯苯基)-恶唑烷-2-酮
  参考文献：
  名称：

  Adams; Segur, Journal of the American Chemical Society, 1923, vol. 45, p. 789

  摘要：

  DOI：

文献信息

• A One-Pot Synthesis of <i>N</i> -Aryl-2-Oxazolidinones and Cyclic Urethanes by the Lewis Base Catalyzed Fixation of Carbon Dioxide into Anilines and Bromoalkanes
  作者：Teemu Niemi、Jesus E. Perea-Buceta、Israel Fernández、Otto-Matti Hiltunen、Vili Salo、Sari Rautiainen、Minna T. Räisänen、Timo Repo

  DOI：10.1002/chem.201602338

  日期：2016.7.18

  catalytic amounts of an organosuperbase such as Barton's base enables this transformation to proceed with high yields and exquisite substrate functional‐group tolerance under ambient CO2 pressure and mild temperature. This report also provides the first proof‐of‐principle for the single‐operation synthesis of elusive seven‐membered ring cyclic urethanes.

  描述了通过将二氧化碳直接插入容易获得的苯胺和二溴代烷烃中的，具有药学意义的N-芳基-恶唑烷酮的多组分组装方法。添加催化量的有机超碱（如Barton碱）可使该转化在环境CO 2压力和温和温度下以高收率和出色的底物官能团耐受性进行。该报告还为难以捉摸的七元环环状氨基甲酸酯的单操作合成提供了第一个原理证明。
• One-Pot Conversion of Carbon Dioxide, Ethylene Oxide, and Amines to 3-Aryl-2-oxazolidinones Catalyzed with Binary Ionic Liquids
  作者：Binshen Wang、Elnazeer H. M. Elageed、Dawei Zhang、Sijuan Yang、Shi Wu、Guirong Zhang、Guohua Gao

  DOI：10.1002/cctc.201300801

  日期：2014.1

  An effective one‐pot method for the conversion of carbon dioxide, ethylene oxide, and amines to 3‐aryl‐2‐oxazolidinones has been developed. This one‐pot method consists of two parallel reactions and a subsequent cascade reaction between the two products of the corresponding parallel reactions. Notably, the binary ionic liquids of 1‐butyl‐3‐methyl‐imidazolium bromide and 1‐butyl‐3‐methyl‐imidazolium

  已开发出一种有效的一锅法，可将二氧化碳，环氧乙烷和胺转化为3-芳基-2-恶唑烷酮。这种单锅法由两个平行反应和相应平行反应的两个产物之间的随后级联反应组成。值得注意的是，溴化1-丁基-3-甲基咪唑鎓和乙酸1-丁基-3-甲基咪唑鎓的二元离子液体对这种新策略显示出协同的催化作用。由于溴的良好亲核性和离去能力，溴化1-丁基-3-甲基咪唑鎓在两个平行反应中必不可少，而乙酸1-丁基-3-甲基咪唑鎓乙酸酯由于随后的级联反应在随后的级联反应中起主要作用。醋酸盐的强碱性。此外，二元离子液体可以使用三次，而不会显着降低催化活性。
• An Eco-friendly, Convenient, and Practical Conversion of Arylamines to Oxazolidinones
  作者：Hang Gong、Nian-Fa Yang、Guo-Jun Deng、Guang-Yi Xu

  DOI：10.1246/cl.2009.584

  日期：2009.6.5

  A one-step procedure for efficient synthesis of oxazolidinone only using ethylene carbonate and arylamines in the presence of 1,4-diazabicyclo[2,2,2]octane (DABCO) was developed. In most cases, moderate to high yield of products were obtained. This reaction can be considered a carbon dioxide fixation reaction since ethylene carbonate was synthesized via reaction of ethylene oxide with carbon dioxide.

  开发了一种仅使用碳酸亚乙酯和芳基胺在 1,4-二氮杂双环[2,2,2]辛烷 (DABCO) 存在下有效合成恶唑烷酮的一步程序。在大多数情况下，获得了中等到高产率的产品。该反应可以被认为是二氧化碳固定反应，因为碳酸亚乙酯是通过环氧乙烷与二氧化碳的反应合成的。
• Bis-aryl Urea Derivatives as Potent and Selective LIM Kinase (Limk) Inhibitors
  作者：Yan Yin、Ke Zheng、Nibal Eid、Shannon Howard、Ji-Hak Jeong、Fei Yi、Jia Guo、Chul Min Park、Mathieu Bibian、Weilin Wu、Pamela Hernandez、HaJeung Park、Yuntao Wu、Jun-Li Luo、Philip V. LoGrasso、Yangbo Feng

  DOI：10.1021/jm501680m

  日期：2015.2.26

  The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 < 25 nM), excellent selectivity against ROCK and JNK kinases (>400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 < 1 mu M), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 mu M inhibited only Limk1 and STK16 with >= 80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.
• Adams; Segur, Journal of the American Chemical Society, 1923, vol. 45, p. 789
  作者：Adams、Segur

  DOI：——

  日期：——