5-hexyl-3-phenyl-oxazolidin-2-one | 137146-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-hexyl-3-phenyl-oxazolidin-2-one
• 英文别名: 5-Hexyl-3-phenyl-1,3-oxazolidin-2-one
• CAS: 137146-09-9
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: VSVXANNIGPUQAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-phenyl-1-amino-2-octanol 、 4-hexyl-1,3-dioxolan-2-one 在 potassium phosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以80%的产率得到5-hexyl-3-phenyl-oxazolidin-2-one
  参考文献：
  名称：

  磷酸钾催化一锅法从环氧化物，胺和大气二氧化碳合成3-芳基-2-恶唑烷酮

  摘要：

  发现磷酸钾是在环境温度下在DMF中的胺，环氧化物和二氧化碳的三组分环加成反应中形成3-芳基-2-恶唑烷酮的高活性催化剂。大气二氧化碳...

  DOI：

  10.1039/c6gc02934e

文献信息

• Selective Formation of α-Cleavage Cycloadduct of Oxirane with Heterocumulene Promoted by High-Coordinated Trialkyltin Complexes
  作者：Katsunori Yano、Nobuyoshi Amishiro、Akio Baba、Haruo Matsuda

  DOI：10.1246/bcsj.64.2661

  日期：1991.9

  In the reaction of monosubstituted oxiranes and heterocumulenes, trialkyltin iodides coordinated by phosphine oxides effectively catalyzed the formation of heterocycles via cleavage at the substituted site in the oxirane ring, while other types of organotin complexes or noncomplexed organotin iodides promoted selective cleavage at the opposite site. A mechanistic investigation demonstrated that the

  在单取代环氧乙烷和杂枯草烯的反应中，氧化膦配位的三烷基锡碘化物通过环氧乙烷环中取代位点的裂解有效催化杂环的形成，而其他类型的有机锡络合物或未络合的有机锡碘化物则促进了相反位点的选择性裂解。机理研究表明，氧化膦的配位促进了环氧乙烷环裂解的逆反应，导致主要形成 α-裂解环加合物。
• [EN] 3,5-SUBSTITUTED-1,3-OXAZOLIDIN-2-ONE DERIVATIVES<br/>[FR] DÉRIVÉS DE 1,3-OXAZOLIDIN-2-ONE 3,5-SUBSTITUÉE
  申请人：MERCK & CO INC

  公开号：WO2009094265A1

  公开（公告）日：2009-07-30

  The present invention is directed to 3,5-disubstituted-l,3-oxazolidin~2-one derivatives which are potentiators of metabotropic glutamate receptors, including the mGluR2 receptor, and which are useful in the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which metabotropic glutamate receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which metabotropic glutamate receptors are involved.

  本发明涉及3,5-二取代-1,3-噁唑烷-2-酮衍生物，其是代谢型谷氨酸受体的增效剂，包括mGluR2受体，适用于治疗或预防与谷氨酸功能障碍有关的神经系统和精神疾病以及代谢型谷氨酸受体参与的疾病。该发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在预防或治疗涉及代谢型谷氨酸受体的疾病中的用途。
• Triethylamine Hydroiodide as a Bifunctional Catalyst for the Solvent-Free Synthesis of 2-Oxazolidinones
  作者：Ryuichi Nishiyori、Ken Okuno、Seiji Shirakawa

  DOI：10.1002/ejoc.202000771

  日期：2020.8.23

  An efficient synthesis of 2‐oxazolidinones from epoxides and isocyanates under solvent‐free conditions, featuring the use of triethylamine hydroiodide as a simple and effective bifunctional organocatalyst is developed.

  开发了在无溶剂条件下由环氧化物和异氰酸酯有效合成2-恶唑烷酮的方法，该方法以三乙胺碘化氢为简单有效的双功能有机催化剂。
• 3,5-SUBSTITUTED-1,3-OXAZOLIDIN-2-ONE DERIVATIVES
  申请人：Brnardic Edward

  公开号：US20100292241A1

  公开（公告）日：2010-11-18

  The present invention is directed to 3,5-disubstituted-1,3-oxazolidin-2-one derivatives which are potentiators of metabotropic glutamate receptors, including the mGluR2 receptor, and which are useful in the treatment or prevention of neuro-ological and psychiatric disorders associated with glutamate dysfunction and diseases in which metabotropic glutamate receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which metabotropic glutamate receptors are involved.

  本发明涉及3,5-二取代-1,3-噁唑烷-2-酮衍生物，其为代谢型谷氨酸受体的增强剂，包括mGluR2受体，可用于治疗或预防与谷氨酸功能失调相关的神经学和精神疾病以及代谢型谷氨酸受体参与的疾病。本发明还涉及包含这些化合物的药物组合物以及这些化合物和组合物在预防或治疗代谢型谷氨酸受体参与的疾病中的使用。
• 3-Aryl-5-phenoxymethyl-1,3-oxazolidin-2-ones as positive allosteric modulators of mGluR2 for the treatment of schizophrenia: Hit-to-lead efforts
  作者：Edward J. Brnardic、Mark E. Fraley、Robert M. Garbaccio、Mark E. Layton、John M. Sanders、Chris Culberson、Marlene A. Jacobson、Brian C. Magliaro、Pete H. Hutson、Julie A. O’Brien、Sarah L. Huszar、Jason M. Uslaner、Kerry L. Fillgrove、Cuyue Tang、Yuhsin Kuo、Sylvie M. Sur、George D. Hartman

  DOI：10.1016/j.bmcl.2010.03.089

  日期：2010.5

  Hit to lead optimization of (5R)-5-hexyl-3-phenyl-1,3-oxazolidin-2-one as a positive allosteric modulator of mGluR2 is described. Improvements in potency and metabolic stability were achieved through SAR on both ends of the oxazolidinone. An optimized lead compound was found to be brain penetrant and active in a rat ketamine-induced hyperlocomotion model for antipsychotic activity. (C) 2010 Elsevier Ltd. All rights reserved.