5,5-dimethyl-3-phenyloxazolidin-2-one | 54044-70-1

• 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: 5,5-dimethyl-3-phenyloxazolidin-2-one
• 英文别名: 2,2-dimethyl-5-phenyl-oxazolidin-4-one；(+/-)-2,2-dimethyl-5-phenyl-oxazolidin-4-one；(+/-)-2,2-Dimethyl-5-phenyl-oxazolidin-4-on；2,2-Dimethyl-5-phenyl-1,3-oxazolidin-4-on；2,2-Dimethyl-5-phenyl-1,3-oxazolidin-4-one
• CAS: 54044-70-1
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: FEFKVCRLZMSHEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-3-phenyloxazolidin-2-one 在 palladium on activated charcoal 正丁基锂 、 potassium tert-butylate 、 氢气 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 75.25h， 生成 5-(Hydroxymethyl)-2,2,3-trimethyl-5-phenyl-1,3-oxazolidin-4-one
  参考文献：
  名称：

  Synthesis and Lipase-Catalyzed Resolution of 5-(Hydroxymethyl)-1,3-dioxolan-4-ones:  Masked Glycerol Analogs as Potential Building Blocks for Pharmaceuticals

  摘要：

  (Hydroxymethyl)-1,3-dioxolan-4-ones from mandelic and lactic acids and 1,5,5-trimethyl-3-phenyloxazolidin-2-one from mandelamide were alpha-alkylated using benzyl chloromethyl ether. Reductive debenzylation of the products of alkylation unmasked the hydroxymethyl groups. The compounds obtained in this fashion were subsequently subjected to lipase-catalyzed resolution in organic media. Depending on the lipase and substrate employed, enantiomeric ratios up to E = 200 were observed. The obtained optically pure compounds can be considered as masked 2-substituted glycerol equivalents, which could be used for the preparation of tertiary (aryloxy)propanolamines, compounds having potential beta-blocking activity.

  DOI：

  10.1021/jo952021v
• 作为产物：
  描述：

  N-isopropyl-2-oxo-2-phenylacetamide 以 甲醇 为溶剂， 以38%的产率得到5,5-dimethyl-3-phenyloxazolidin-2-one
  参考文献：
  名称：

  N-烷基-α-氧代酰胺的光化学反应

  摘要：

  的光解Ñ烷基-α-oxoamides得到恶唑烷-4-酮或β内酰胺类作为主要产品为在的情况下，NN二烷基-α-oxoamides。N-环己基苯甲酰基甲酰胺在水性酸性介质中光解过程中环己酮的形成最合理地解释为中间产物N-环己叉基亚甲基酰胺的水解。

  DOI：

  10.1039/p19810001357

文献信息

• Fischer et al., Chemische Berichte, 1932, vol. 65, p. 1032,1035
  作者：Fischer et al.

  DOI：——

  日期：——
• AOYAMA HIROMU; SAKAMOTO MASAMI; OMOTE YOSHIMORI, J. CHEM. SOC. PERKIN TRANS., PART 1, 1981, NO 5, 1357-1359
  作者：AOYAMA HIROMU、 SAKAMOTO MASAMI、 OMOTE YOSHIMORI

  DOI：——

  日期：——
• Synthesis and Lipase-Catalyzed Resolution of 5-(Hydroxymethyl)-1,3-dioxolan-4-ones:  Masked Glycerol Analogs as Potential Building Blocks for Pharmaceuticals
  作者：Robert P. Hof、Richard M. Kellogg

  DOI：10.1021/jo952021v

  日期：1996.1.1

  (Hydroxymethyl)-1,3-dioxolan-4-ones from mandelic and lactic acids and 1,5,5-trimethyl-3-phenyloxazolidin-2-one from mandelamide were alpha-alkylated using benzyl chloromethyl ether. Reductive debenzylation of the products of alkylation unmasked the hydroxymethyl groups. The compounds obtained in this fashion were subsequently subjected to lipase-catalyzed resolution in organic media. Depending on the lipase and substrate employed, enantiomeric ratios up to E = 200 were observed. The obtained optically pure compounds can be considered as masked 2-substituted glycerol equivalents, which could be used for the preparation of tertiary (aryloxy)propanolamines, compounds having potential beta-blocking activity.
• Photochemical reactions of N-alkyl-α-oxoamides
  作者：Hiromu Aoyama、Masami Sakamoto、Yoshimori Omote

  DOI：10.1039/p19810001357

  日期：——

  Photolysis of N-alkyl-α-oxoamides gave oxazolidin-4-ones or β-lactams as major products as in the case of NN-dialkyl-α-oxoamides. The formation of cyclohexanone in the photolysis of N-cyclohexylbenzoylformamide in an aqueous acidic medium was most reasonably explained by hydrolysis of an intermediate, N-cyclohexylidenemandelamide.

  的光解Ñ烷基-α-oxoamides得到恶唑烷-4-酮或β内酰胺类作为主要产品为在的情况下，NN二烷基-α-oxoamides。N-环己基苯甲酰基甲酰胺在水性酸性介质中光解过程中环己酮的形成最合理地解释为中间产物N-环己叉基亚甲基酰胺的水解。