(3aS,4S,6R,6aS)-6-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1'-phenyldihydro-6H-spiro[furo[3,4-d][1,3]dioxole-4,4'-imidazolidine]-2',5'-dione | 153796-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3aS,4S,6R,6aS)-6-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1'-phenyldihydro-6H-spiro[furo[3,4-d][1,3]dioxole-4,4'-imidazolidine]-2',5'-dione
• CAS: 153796-95-3
• 化学式: C₁₇H₂₀N₂O₇
• 分子量: 364.355
• InChiKey: WTOXMOZMJFNARK-SWAFEPEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.29
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  117.56
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6R,6aS)-6-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1'-phenyldihydro-6H-spiro[furo[3,4-d][1,3]dioxole-4,4'-imidazolidine]-2',5'-dione 在 camphor-10-sulfonic acid 、 三氟乙酸 作用下， 生成 (5S,7S,8R,9S)-7-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8,9-dihydroxy-3-phenyl-6-oxa-1,3-diaza-spiro[4.4]nonane-2,4-dione
  参考文献：
  名称：

  Anomeric spirohydantoins of mannofuranose: Approaches to novel anomeric amino acids by an oxidative ring contraction

  摘要：

  Bromine-induced oxidative ring contraction of an alpha-amino-delta-lactone gave a mixture of alpha-aminotetrahydrofurancarboxylic esters which may allow the preparation of stable amino acid derivatives at the anomeric position of mannofuranose. The synthesis of N-phenylhydantoins at the anomeric position of mannofuranose is reported.

  DOI：

  10.1016/s0040-4039(00)61745-8
• 作为产物：
  描述：

  (3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3'-phenylspiro[6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4,5'-imidazolidine]-2',4'-dione 在 溶剂黄146 作用下， 以92%的产率得到(3aS,4S,6R,6aS)-6-((R)-1,2-dihydroxyethyl)-2,2-dimethyl-1'-phenyldihydro-6H-spiro[furo[3,4-d][1,3]dioxole-4,4'-imidazolidine]-2',5'-dione
  参考文献：
  名称：

  Anomeric spirohydantoins of mannofuranose: Approaches to novel anomeric amino acids by an oxidative ring contraction

  摘要：

  Bromine-induced oxidative ring contraction of an alpha-amino-delta-lactone gave a mixture of alpha-aminotetrahydrofurancarboxylic esters which may allow the preparation of stable amino acid derivatives at the anomeric position of mannofuranose. The synthesis of N-phenylhydantoins at the anomeric position of mannofuranose is reported.

  DOI：

  10.1016/s0040-4039(00)61745-8