3-phenyl-5-p-tolyloxymethyl-oxazolidin-2-one | 5255-95-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-phenyl-5-p-tolyloxymethyl-oxazolidin-2-one
• 英文别名: 3-Phenyl-5-(p-tolyloxymethyl)oxazolidin-2-one；5-[(4-methylphenoxy)methyl]-3-phenyl-1,3-oxazolidin-2-one
• CAS: 5255-95-8
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: XGAKSPGMZGHDTM-UHFFFAOYSA-N

物化性质

• 熔点：
  197-198 °C
• 沸点：
  417.8±14.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对叔丁基苯基1-(2,3-环氧)丙基醚 、 2,2,2-三氯-N-苯基乙酰胺 反应 6.0h， 生成 3-phenyl-5-p-tolyloxymethyl-oxazolidin-2-one
  参考文献：
  名称：

  来自缩水甘油醚与酰胺的反应的 2-恶唑烷酮

  摘要：

  酰胺与芳基缩水甘油醚的反应以叔胺为催化剂进行。2-恶唑烷酮衍生物由三氯乙酰苯胺或三氟乙酰苯胺与芳基缩水甘油醚反应得到。乙酰苯胺与苯基缩水甘油醚反应发生酰基迁移。

  DOI：

  10.1246/bcsj.39.2490

文献信息

• 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.
• 2-Oxazolidones from Glycidyl Ether Reactions with Acid Amides
  作者：Yoshio Iwakura、Shin-ichi Izawa

  DOI：10.1246/bcsj.39.2490

  日期：1966.11

  The reaction between acid amides and aryl glycidyl ethers was carried out using tertiary amine as the catalyst. 2-Oxazolidone derivatives were obtained by the reaction of trichloroacetanilide or trifluoroacetanilide with aryl glycidyl ether. Acyl migration occurred in the reaction of acetanilide with phenyl glycidyl ether.

  酰胺与芳基缩水甘油醚的反应以叔胺为催化剂进行。2-恶唑烷酮衍生物由三氯乙酰苯胺或三氟乙酰苯胺与芳基缩水甘油醚反应得到。乙酰苯胺与苯基缩水甘油醚反应发生酰基迁移。

表征谱图