1'-(2-Phenylethyl)-1,2,4,9-tetrahydro-2'H,5'H-spiro[carbazole-3,4'-imidazolidine]-2',5'-dione | 893428-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1'-(2-Phenylethyl)-1,2,4,9-tetrahydro-2'H,5'H-spiro[carbazole-3,4'-imidazolidine]-2',5'-dione
• 英文别名: 3'-(2-phenylethyl)spiro[1,2,4,9-tetrahydrocarbazole-3,5'-imidazolidine]-2',4'-dione
• CAS: 893428-22-3
• 化学式: C₂₂H₂₁N₃O₂
• 分子量: 359.428
• InChiKey: JTDKIUJOWHPHDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1'-(2-Phenylethyl)-1,2,4,9-tetrahydro-2'H,5'H-spiro[carbazole-3,4'-imidazolidine]-2',5'-dione
  参考文献：
  名称：

  Upscaling the Solid-Phase Synthesis of a Tetrahydrocarbazole in Chemical Development

  摘要：

  A multigram solid-phase synthesis of tetrahydrocarbazole 1 was developed based a milligram-scale synthesis from Automated Medicinal Chemistry (Koppitz, M.; Reinhardt, G.; van Lingen, A. Tetrahedron Lett. 2005, 46, 911- 914). It was shown that a fast scale-up by a factor of 2000 of the solid-phase synthesis is possible in this case. Highly loaded Rink Amide resin was used, and the eight-step-synthesis was performed within 5 days, yielding 35 g (34%) of desired product 1.

  DOI：

  10.1021/op0502607