(4R)-1-<(benzyloxy)methyl>-3-(difluoromethyl)-3'-methylspiro-2,2',5(3'H)-trione | 138573-17-8

• 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: (4R)-1-<(benzyloxy)methyl>-3-(difluoromethyl)-3'-methylspiro-2,2',5(3'H)-trione
• CAS: 138573-17-8
• 化学式: C₂₀H₁₈F₂N₄O₄
• 分子量: 416.384
• InChiKey: RDQGYWCJRVCBRB-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.19
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4R)-1-<(benzyloxy)methyl>-3-(difluoromethyl)-3'-methylspiro-2,2',5(3'H)-trione 在 钯 氢气 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以94%的产率得到(4R)-3-(Difluoromethyl)-3'-methylspiro-2,2',5(3'H)-trione
  参考文献：
  名称：

  Preparation of optically pure 3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione by combination of optical resolution and racemization

  摘要：

  Optically pure 3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione was prepared by optical resolution using brucine as a resolving agent. The resulting optically pure spirohydantoin was racemized by refluxing in 1,2-dichlorobenzene for 17 h, or more effectively upon heating in 10% HCl at 90-degrees-C for 2 h. In the acid-catalyzed racemization, the introduction of difluoromethyl group at the 3-nitrogen of hydantoin ring increased the racemization rate, while the introduction of methyl group at the 3-nitrogen reduced it. These results suggest that the acid-catalyzed racemization proceeds via the N-acyliminium ion generated by the cleavage of the N3-C4 bond of the spirohydantoin ring.

  DOI：

  10.1021/jo00031a043
• 作为产物：
  描述：

  (+)-3'-Methylspiro-2,2',5(3'H)-trione 在 sodium hydride 作用下， 反应 17.0h， 生成 (4R)-1-<(benzyloxy)methyl>-3-(difluoromethyl)-3'-methylspiro-2,2',5(3'H)-trione
  参考文献：
  名称：

  Preparation of optically pure 3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione by combination of optical resolution and racemization

  摘要：

  Optically pure 3'-methylspiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-trione was prepared by optical resolution using brucine as a resolving agent. The resulting optically pure spirohydantoin was racemized by refluxing in 1,2-dichlorobenzene for 17 h, or more effectively upon heating in 10% HCl at 90-degrees-C for 2 h. In the acid-catalyzed racemization, the introduction of difluoromethyl group at the 3-nitrogen of hydantoin ring increased the racemization rate, while the introduction of methyl group at the 3-nitrogen reduced it. These results suggest that the acid-catalyzed racemization proceeds via the N-acyliminium ion generated by the cleavage of the N3-C4 bond of the spirohydantoin ring.

  DOI：

  10.1021/jo00031a043