(4R)-1-<(Benzyloxy)methyl>-3'-methylspiro-2,2',5(3'H)-trione | 138573-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (4R)-1-<(Benzyloxy)methyl>-3'-methylspiro-2,2',5(3'H)-trione
• 英文别名: (4R)-3-methyl-3'-(phenylmethoxymethyl)spiro[1H-quinazoline-4,5'-imidazolidine]-2,2',4'-trione
• CAS: 138573-15-6
• 化学式: C₁₉H₁₈N₄O₄
• 分子量: 366.376
• InChiKey: ADSBMBPLKVINEQ-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-1-<(Benzyloxy)methyl>-3'-methylspiro-2,2',5(3'H)-trione 在 钯 氢气 、 sodium hydride 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 16.5h， 生成 (4R)-3,3'-Dimethylspiro-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：

  苄基氯甲基醚 、 (+)-3'-Methylspiro-2,2',5(3'H)-trione 在 sodium hydride 作用下， 生成 (4R)-1-<(Benzyloxy)methyl>-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