3-(4-Chlorophenyl)-1'-methylspiro[1,3-oxazolidine-5,4'-7-oxabicyclo[4.1.0]heptane]-2,4-dione | 1234623-24-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 3-(4-Chlorophenyl)-1'-methylspiro[1,3-oxazolidine-5,4'-7-oxabicyclo[4.1.0]heptane]-2,4-dione
• 英文别名: 3-(4-chlorophenyl)-1'-methylspiro[1,3-oxazolidine-5,4'-7-oxabicyclo[4.1.0]heptane]-2,4-dione
• CAS: 1234623-24-5
• 化学式: C₁₅H₁₄ClNO₄
• 分子量: 307.733
• InChiKey: XKZOSZUHHDOKFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(4-Chlorophenyl)-8-methyl-4-methylidene-1-oxa-3-azaspiro[4.5]dec-7-en-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以89%的产率得到3-(4-Chlorophenyl)-1'-methylspiro[1,3-oxazolidine-5,4'-7-oxabicyclo[4.1.0]heptane]-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

• 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.