5-(tricyclo[3.3.1.13,7]dec-1-yl)-5-methyl-2-pyrrolidinone | 888030-24-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-(tricyclo[3.3.1.13,7]dec-1-yl)-5-methyl-2-pyrrolidinone
• 英文别名: 5-(tricyclo[3.3.1.1^3,7]dec-1-yl)-5-methyl-2-pyrrolidinone；(RS)-5-(adamantan-1-yl)-5-methylpyrrolidin-2-one
• CAS: 888030-24-8
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: AQDGSIFOXSKBCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-(tricyclo[3.3.1.13,7]dec-1-yl)-5-methyl-2-pyrrolidinone 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 49.0h， 生成
  参考文献：
  名称：

  Heterocyclic rimantadine analogues with antiviral activity

  摘要：

  2-(1-Adamantyl)-2-methyl-pyrrolidines 3 and 4, 2-(1-adamatityl)-2-methyl-azetidines 5 and 6, and 2-(1-adamantyl)-2-methyl-aziridines 7 and 8 were synthesized and tested for their antiviral activity against influenza A. Parent molecules 3, 5, and 7 contain the alpha-methyl-1-adimantan-methanamine 2 pharmacophoric moiety (rimantadine). The ring size effect on anti-influenza A activity was investigated. Pyrrolidine 3 was the most potent anti-influenza virus A compound, 9-fold more potent than rimantadine 2, 27-fold more potent than amantadine 1, and 22-fold more potent than ribavirin. Azetidines 5 and 6 were both markedly active against influenza A H2N2 virus, 10- to 20-fold more potent than amantadine. Aziridine 7 was almost devoid of any activity against H2N2 virus but exhibited borderline activity against H3N2 influenza A strain. Thus, it appears that changing the five-, to four- to a three-membered ring results in a drop of activity against influenza A virus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.056
• 作为产物：
  描述：

  4-(tricyclo[3.3.1.13,7]dec-1-yl)-4-nitropentanoic acid 在 盐酸 、 氢气 、 镍 作用下， 以 乙醇 为溶剂， 50.0~75.0 ℃ 、344.74 kPa 条件下， 反应 7.0h， 生成 5-(tricyclo[3.3.1.13,7]dec-1-yl)-5-methyl-2-pyrrolidinone
  参考文献：
  名称：

  Heterocyclic rimantadine analogues with antiviral activity

  摘要：

  2-(1-Adamantyl)-2-methyl-pyrrolidines 3 and 4, 2-(1-adamatityl)-2-methyl-azetidines 5 and 6, and 2-(1-adamantyl)-2-methyl-aziridines 7 and 8 were synthesized and tested for their antiviral activity against influenza A. Parent molecules 3, 5, and 7 contain the alpha-methyl-1-adimantan-methanamine 2 pharmacophoric moiety (rimantadine). The ring size effect on anti-influenza A activity was investigated. Pyrrolidine 3 was the most potent anti-influenza virus A compound, 9-fold more potent than rimantadine 2, 27-fold more potent than amantadine 1, and 22-fold more potent than ribavirin. Azetidines 5 and 6 were both markedly active against influenza A H2N2 virus, 10- to 20-fold more potent than amantadine. Aziridine 7 was almost devoid of any activity against H2N2 virus but exhibited borderline activity against H3N2 influenza A strain. Thus, it appears that changing the five-, to four- to a three-membered ring results in a drop of activity against influenza A virus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.056

文献信息

• Photocatalytic α‐Tertiary Amine Synthesis via C−H Alkylation of Unmasked Primary Amines
  作者：Alison S. H. Ryder、William B. Cunningham、George Ballantyne、Tom Mules、Anna G. Kinsella、Jacob Turner‐Dore、Catherine M. Alder、Lee J. Edwards、Blandine S. J. McKay、Matthew N. Grayson、Alexander J. Cresswell

  DOI：10.1002/anie.202005294

  日期：2020.8.24

  transfer (HAT) catalyst, provides a direct synthesis of α‐tertiary amines, or their corresponding γ‐lactams. We anticipate that this methodology will inspire new retrosynthetic disconnections for substituted amine derivatives in organic synthesis, and particularly for challenging α‐tertiary primary amines.

  长期以来，通过 C-H 官能化实现 α,α,α-三取代（α-叔）伯胺的实用催化进入一直被认为是合成工具箱中的一个关键空白。我们报告了一个简单且可扩展的解决方案，不需要对氨基进行任何原位保护，并以 100% 的原子经济性进行。我们的策略使用有机光催化剂与叠氮离子结合作为氢原子转移（HAT）催化剂，提供了α-叔胺或其相应的γ-内酰胺的直接合成。我们预计这种方法将激发有机合成中取代胺衍生物的新逆合成断开，特别是对于具有挑战性的 α-叔伯胺。