5,7-Diazaadamantan-2-ol | 53120-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5,7-Diazaadamantan-2-ol
• 英文别名: 1,3-Diaza-6-hydroxyadamantan；1,3-diaza-adamantan-6-ol；6-Hydroxy-1,3-diazaadamantane；1,3-diazatricyclo[3.3.1.13,7]decan-6-ol
• CAS: 53120-58-4
• 化学式: C₈H₁₄N₂O
• 分子量: 154.212
• InChiKey: AARLJNADOYPNQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,3-Bis(phenylthio)-5,7-diazaadamantan-2-one 在 镍 作用下， 以 异丙醇 为溶剂， 反应 10.0h， 以21%的产率得到5,7-Diazaadamantan-2-ol
  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

• Stetter et al., Chemische Berichte, 1959, vol. 92, p. 2057,2060
  作者：Stetter et al.

  DOI：——

  日期：——
• ASLANOV X. A.; INOYATOVA D. A.; KOSOVSKIJ A. V.; ATABAEV R., SB. NAUCH. TR. TASHKENT. YH-T, 1979, HO 595, 83-86
  作者：ASLANOV X. A.、 INOYATOVA D. A.、 KOSOVSKIJ A. V.、 ATABAEV R.

  DOI：——

  日期：——
• HYDROPHILIC CROSSLINKED POLYMER
  申请人：Joehnck Matthias

  公开号：US20110091727A1

  公开（公告）日：2011-04-21

  The present invention relates to a hydrophilic crosslinked polymer, preferably in the form of porous particles, and to the preparation and use thereof. The polymer according to the invention is produced by polymerisation from chain-forming hydrophilic vinyl ethers and crosslinking, preferably heterocyclic divinyl ethers.
• US7951885B2
  申请人：——

  公开号：US7951885B2

  公开（公告）日：2011-05-31
• US8765897B2
  申请人：——

  公开号：US8765897B2

  公开（公告）日：2014-07-01