5,7-Diazaadamantan-2-one | 20397-57-3

• 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: 5,7-Diazaadamantan-2-one
• 英文别名: 1,3-diaza-6-adamantanone；1,3-Diazamantan-6-on；6-Oxo-1,3-diaza-adamantan；1,3-Diazaadamantanon；1.3-diaza-adamantan-6-one；1,3-Diazaadamantan-6-one；1,3-diazatricyclo[3.3.1.13,7]decan-6-one
• CAS: 20397-57-3
• 化学式: C₈H₁₂N₂O
• 分子量: 152.196
• InChiKey: BDWJSGMOFNDOAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,7-Diazaadamantan-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到5,7-Diazaadamantan-2-one N-oxide
  参考文献：
  名称：

  Face Selection in Reactions of 5,7-Diazaadamantan-2-one Derivatives: Mutual Influence of Remote Substituents

  摘要：

  When one of the nitrogen atoms in 5,7-diazaadamantan-2-one(1) (4) is quaternized, for example, as in 3-O, carbonyl reduction occurs principally at the zu face to give alcohol (E)-6-O, in accord with Cieplak-type transition state hyperconjugation. The ratio in this reduction is somewhat less than in that of the previously reported monoaza N-oxide 2-O, which is attributed to the effect of hyperconjugation in the initial state of 3-O. If the parent diaza ketone 4 is reduced first to the corresponding diaza alcohol 5 and if this is then oxidized to 6-O, the Z-isomer is the principal product. The stereochemistry of this latter reaction is also considered to be a result of extended hyperconjugation. Virtually identical data are obtained with the methyl iodide salts. It is concluded that the effect of remote substituents is mutual and that this fact can be exploited to influence, even reverse, the stereochemical outcome of a synthesis by manipulation of the sequence of the individual steps.

  DOI：

  10.1021/jo00129a014
• 作为产物：
  描述：

  5,7-Diazaadamantan-2-ol 在 Celite 、 silver carbonate 作用下， 以 苯 为溶剂， 以83%的产率得到5,7-Diazaadamantan-2-one
  参考文献：
  名称：

  Face Selection in Reactions of 5,7-Diazaadamantan-2-one Derivatives: Mutual Influence of Remote Substituents

  摘要：

  When one of the nitrogen atoms in 5,7-diazaadamantan-2-one(1) (4) is quaternized, for example, as in 3-O, carbonyl reduction occurs principally at the zu face to give alcohol (E)-6-O, in accord with Cieplak-type transition state hyperconjugation. The ratio in this reduction is somewhat less than in that of the previously reported monoaza N-oxide 2-O, which is attributed to the effect of hyperconjugation in the initial state of 3-O. If the parent diaza ketone 4 is reduced first to the corresponding diaza alcohol 5 and if this is then oxidized to 6-O, the Z-isomer is the principal product. The stereochemistry of this latter reaction is also considered to be a result of extended hyperconjugation. Virtually identical data are obtained with the methyl iodide salts. It is concluded that the effect of remote substituents is mutual and that this fact can be exploited to influence, even reverse, the stereochemical outcome of a synthesis by manipulation of the sequence of the individual steps.

  DOI：

  10.1021/jo00129a014

文献信息

• Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors
  作者：Dmitriy Shcherbakov、Dmitriy Baev、Mikhail Kalinin、Alexander Dalinger、Varvara Chirkova、Svetlana Belenkaya、Aleksei Khvostov、Dmitry Krut’ko、Aleksei Medved’ko、Ekaterina Volosnikova、Elena Sharlaeva、Daniil Shanshin、Tatyana Tolstikova、Olga Yarovaya、Rinat Maksyutov、Nariman Salakhutdinov、Sergey Vatsadze

  DOI：10.1021/acsmedchemlett.1c00299

  日期：2022.1.13
• IMPROVED SYNTHESIS OF 1,3-DIAZA-6-ADAMANTANONE
  作者：Timothy A. Lewis、Gurmit Grewal

  DOI：10.1080/00304940309355865

  日期：2003.10
• Face Selection in Reactions of 5,7-Diazaadamantan-2-one Derivatives: Mutual Influence of Remote Substituents
  作者：Elena M. Gonikberg、William J. le Noble

  DOI：10.1021/jo00129a014

  日期：1995.12

  When one of the nitrogen atoms in 5,7-diazaadamantan-2-one(1) (4) is quaternized, for example, as in 3-O, carbonyl reduction occurs principally at the zu face to give alcohol (E)-6-O, in accord with Cieplak-type transition state hyperconjugation. The ratio in this reduction is somewhat less than in that of the previously reported monoaza N-oxide 2-O, which is attributed to the effect of hyperconjugation in the initial state of 3-O. If the parent diaza ketone 4 is reduced first to the corresponding diaza alcohol 5 and if this is then oxidized to 6-O, the Z-isomer is the principal product. The stereochemistry of this latter reaction is also considered to be a result of extended hyperconjugation. Virtually identical data are obtained with the methyl iodide salts. It is concluded that the effect of remote substituents is mutual and that this fact can be exploited to influence, even reverse, the stereochemical outcome of a synthesis by manipulation of the sequence of the individual steps.