3-(4-chloro-phenyl)-5,5-dimethyl-oxazolidine-2,4-dione | 27125-28-6

• 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: 3-(4-chloro-phenyl)-5,5-dimethyl-oxazolidine-2,4-dione
• 英文别名: 3-(4-Chlor-phenyl)-5,5-dimethyl-oxazolidin-2,4-dion；3-(4-Chlorophenyl)-5,5-dimethyl-1,3-oxazolidine-2,4-dione
• CAS: 27125-28-6
• 化学式: C₁₁H₁₀ClNO₃
• 分子量: 239.658
• InChiKey: HFAYIHHFZPFECH-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  317.8±44.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-chloro-phenyl)-5,5-dimethyl-oxazolidine-2,4-dione 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以47%的产率得到N-(4-氯苯基)-2-羟基-2-甲基丙酰胺
  参考文献：
  名称：

  Versatile synthesis of quaternary 1,3-oxazolidine-2,4-diones and their use in the preparation of α-hydroxyamides

  摘要：

  A new approach to the synthesis of 1,3-oxazolidine-2,4-diones, via a two-step reaction sequence, starting from the readily available alpha-ketols and isocyanates, is reported. The condensation of the latter led to the key precursors 4-methylene-2-oxazolidinones, which are converted into the diones by an oxidative cleavage of the exocyclic double bond. Thus, 5,5-disubstituted 1,3-oxazolidine-2,4-diones can be accessed in good yields from the appropriate functionalized alpha-ketols. Moreover, two alternative routes are also described either by functionalization of 4-oxazolin-2-ones or by alkylation of the 1,3-oxazolidine-2,4-dione core previously prepared. Upon hydrolysis of the 1,3-oxazolidine-2,4-diones, a series of alpha-hydroxyamides bearing a quaternary stereocenter were obtained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.034
• 作为产物：
  描述：

  3-(4-chlorophenyl)-5,5-dimethyl-4-methyleneoxazolidin-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以97%的产率得到3-(4-chloro-phenyl)-5,5-dimethyl-oxazolidine-2,4-dione
  参考文献：
  名称：

  Versatile synthesis of quaternary 1,3-oxazolidine-2,4-diones and their use in the preparation of α-hydroxyamides

  摘要：

  A new approach to the synthesis of 1,3-oxazolidine-2,4-diones, via a two-step reaction sequence, starting from the readily available alpha-ketols and isocyanates, is reported. The condensation of the latter led to the key precursors 4-methylene-2-oxazolidinones, which are converted into the diones by an oxidative cleavage of the exocyclic double bond. Thus, 5,5-disubstituted 1,3-oxazolidine-2,4-diones can be accessed in good yields from the appropriate functionalized alpha-ketols. Moreover, two alternative routes are also described either by functionalization of 4-oxazolin-2-ones or by alkylation of the 1,3-oxazolidine-2,4-dione core previously prepared. Upon hydrolysis of the 1,3-oxazolidine-2,4-diones, a series of alpha-hydroxyamides bearing a quaternary stereocenter were obtained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.034

文献信息

• N-Substituted Oxazolidinediones
  作者：Seymour L. Shapiro、Ira M. Rose、Frank C. Testa、Eric Roskin、Louis Freedman

  DOI：10.1021/ja01533a042

  日期：1959.12
• DOVLATYAN V. V.; AMBARTSUMYAN EH. N.; BAGRAZYAN S. G.; AMBARTSUMYAN M. N., XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1975, HO 6, 745-747
  作者：DOVLATYAN V. V.、 AMBARTSUMYAN EH. N.、 BAGRAZYAN S. G.、 AMBARTSUMYAN M. N.

  DOI：——

  日期：——
• Versatile synthesis of quaternary 1,3-oxazolidine-2,4-diones and their use in the preparation of α-hydroxyamides
  作者：Omar Merino、Blanca M. Santoyo、Luisa E. Montiel、Hugo A. Jiménez-Vázquez、L. Gerardo Zepeda、Joaquín Tamariz

  DOI：10.1016/j.tetlet.2010.05.034

  日期：2010.7

  A new approach to the synthesis of 1,3-oxazolidine-2,4-diones, via a two-step reaction sequence, starting from the readily available alpha-ketols and isocyanates, is reported. The condensation of the latter led to the key precursors 4-methylene-2-oxazolidinones, which are converted into the diones by an oxidative cleavage of the exocyclic double bond. Thus, 5,5-disubstituted 1,3-oxazolidine-2,4-diones can be accessed in good yields from the appropriate functionalized alpha-ketols. Moreover, two alternative routes are also described either by functionalization of 4-oxazolin-2-ones or by alkylation of the 1,3-oxazolidine-2,4-dione core previously prepared. Upon hydrolysis of the 1,3-oxazolidine-2,4-diones, a series of alpha-hydroxyamides bearing a quaternary stereocenter were obtained. (C) 2010 Elsevier Ltd. All rights reserved.