1,3-Bis(phenylthio)-5,7-diazaadamantan-2-one | 78693-62-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,3-Bis(phenylthio)-5,7-diazaadamantan-2-one
• 英文别名: 5,7-bis-phenylsulfanyl-1,3-diaza-adamantan-6-one；5,7-Bis-phenylmercapto-1,3-diaza-adamantan-6-on；5,7-Bis(phenylsulfanyl)-1,3-diazatricyclo[3.3.1.13,7]decan-6-one
• CAS: 78693-62-6
• 化学式: C₂₀H₂₀N₂OS₂
• 分子量: 368.524
• InChiKey: OFCYPZJCDMXDIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-Bis(phenylthio)-5,7-diazaadamantan-2-one 在 Celite 、 镍 、 silver carbonate 作用下， 以 异丙醇 、 苯 为溶剂， 反应 10.0h， 生成 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：

  sodium thiophenolate 在 乙醇 作用下， 生成 1,3-Bis(phenylthio)-5,7-diazaadamantan-2-one
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

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

  DOI：——

  日期：——
• 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.