6-hydroxy-3-oxadiamantane | 1167987-96-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 6-hydroxy-3-oxadiamantane
• 英文别名: 6-Hydroxy-3-oxadiamantane；3-oxapentacyclo[7.3.1.14,12.02,7.06,11]tetradecan-6-ol
• CAS: 1167987-96-3
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: SQJAHAPRLKKDER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-hydroxy-3-oxadiamantane 在 吡啶 、 二溴亚砜 作用下， 以99%的产率得到6-bromo-3-oxadiamantane
  参考文献：
  名称：

  Oxygen-Doped Nanodiamonds: Synthesis and Functionalizations

  摘要：

  Oxadiamondoids representing a new class of carbon nanoparticles were prepared from the respective diamondoid ketones via an effective two-step procedure involving addition of methyl magnesium iodide and oxidation with trifluoroperacetic acid in trifluoroacetic acid. The reactivities of the oxacages are determined by the position of the dopant and are in good agreement with computational predictions.

  DOI：

  10.1021/ol901089h
• 作为产物：
  描述：

  3-oxadiamantane 在 硝酸 、 水 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到6-hydroxy-3-oxadiamantane
  参考文献：
  名称：

  Oxygen-Doped Nanodiamonds: Synthesis and Functionalizations

  摘要：

  Oxadiamondoids representing a new class of carbon nanoparticles were prepared from the respective diamondoid ketones via an effective two-step procedure involving addition of methyl magnesium iodide and oxidation with trifluoroperacetic acid in trifluoroacetic acid. The reactivities of the oxacages are determined by the position of the dopant and are in good agreement with computational predictions.

  DOI：

  10.1021/ol901089h

文献信息

• Aerobic oxidations with N -hydroxyphthalimide in trifluoroacetic acid
  作者：Pavel A. Gunchenko、Jing Li、Bifu Liu、Hongyan Chen、Alexander E. Pashenko、Vladyslav V. Bakhonsky、Tatyana S. Zhuk、Andrey A. Fokin

  DOI：10.1016/j.mcat.2017.12.017

  日期：2018.3

  highly polar trifluoroacetic acid as a media for the metal-free aerobic oxidations propagated by phthalimide N-oxyl- (PINO) radical was demonstrated experimentally utilizing N-hydroxyphthalimide (NHPI) as a catalyst and HNO3 or NaNO2 as promoters. The oxidations of toluene, cyclohexane, adamantane, diamantane, and 3-oxadiamantane gave, respectively, benzaldehyde, adipic acid, 1-hydroxyadamantane, 1-hydroxydiamantane

  利用N-羟基邻苯二甲酰亚胺（NHPI）作为催化剂和HNO 3或NaNO 2，通过实验证明了高极性三氟乙酸作为邻苯二甲酰亚胺N-氧基-（PINO）自由基传播的无氧好氧氧化反应的介质的潜力。作为发起人。甲苯，环己烷，金刚烷，金刚烷和3-恶二金刚烷的氧化在高转化率下可分别产生高达90％的选择性的苯甲醛，己二酸，1-羟基金刚烷，1-羟基二金刚烷和9-羟基-3-恶二金刚烷。起始材料。根据M06-2X和B3LYP-D3层的密度泛函理论计算，甲苯和苯甲醇与高度亲电的PINO自由基提取氢的极化过渡结构（TS）通过非共价相互作用（π–π）得以稳定。堆叠）。对于从苯甲醛中脱除H的化合物，TS中不存在这种额外的稳定作用，因此可阻止其过氧化为苯甲酸。