5-methyl-3-(o-iodophenyl)-2,4-oxazolidinedione | 1262144-65-9

• 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-methyl-3-(o-iodophenyl)-2,4-oxazolidinedione
• 英文别名: 3-(2-iodophenyl)-5-methyl-1,3-oxazolidine-2,4-dione
• CAS: 1262144-65-9
• 化学式: C₁₀H₈INO₃
• 分子量: 317.083
• InChiKey: QDOUHZMOWYAJCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-methyl-3-(o-iodophenyl)-2,4-oxazolidinedione 、 苯甲醛 在 lithium diisopropyl amide 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以76.6%的产率得到5-(α-hydroxybenzyl)-5-methyl-3-(o-iodophenyl)-2,4-oxazolidinedione
  参考文献：
  名称：

  Stereoselective lithiation and alkylation and aldol reactions of chiral 5-methyl-3-(o-aryl)-oxazolidinones

  摘要：

  Alkylation and aldol reactions carried out on axially chiral diastereoenriched oxazolidinedione derivatives were found to be highly stereoselective with respect to substitution at the 5-position of the oxazolidindione ring Thus diastereoenriched 5-methyl-3 (o-lodophenyl)-2-thioxo-4-oxazolidinone and 5-methyl-3-(o-aryl)-2 4 oxazolidinediones were prepared and lithiated at C-5 of the oxazolicline ring and the subsequent electrophilic quench with alkyl halides or benzaldehyde yielded products with the same diastereomer ratios as the starting materials (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.008
• 作为产物：
  描述：

  L(-)-乳酸乙酯 、 异氰酸-2-碘苯酯 在 sodium 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 5-methyl-3-(o-iodophenyl)-2,4-oxazolidinedione
  参考文献：
  名称：

  Stereoselective lithiation and alkylation and aldol reactions of chiral 5-methyl-3-(o-aryl)-oxazolidinones

  摘要：

  Alkylation and aldol reactions carried out on axially chiral diastereoenriched oxazolidinedione derivatives were found to be highly stereoselective with respect to substitution at the 5-position of the oxazolidindione ring Thus diastereoenriched 5-methyl-3 (o-lodophenyl)-2-thioxo-4-oxazolidinone and 5-methyl-3-(o-aryl)-2 4 oxazolidinediones were prepared and lithiated at C-5 of the oxazolicline ring and the subsequent electrophilic quench with alkyl halides or benzaldehyde yielded products with the same diastereomer ratios as the starting materials (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.008