3-(1-Hydroxyethyl)-2,2-dimethylcyclobutylacetaldehyde | 72257-92-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1-Hydroxyethyl)-2,2-dimethylcyclobutylacetaldehyde
• 英文别名: 2-[(1R,3R)-3-(1-hydroxyethyl)-2,2-dimethylcyclobutyl]acetaldehyde
• CAS: 72257-92-2
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: TYCNIVYLIXADIT-NPPUSCPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-[3-(2-hydroxyethyl)-2,2-dimethylcyclobutyl]ethanol 在 四氧化锇 作用下， 以 乙醚 为溶剂， 反应 30.0h， 以30%的产率得到3-(1-Hydroxyethyl)-2,2-dimethylcyclobutylacetaldehyde
  参考文献：
  名称：

  Carbonyl Compounds by Osmium Tetroxide Oxidation: Preferential Oxidation of Primary over Secondary Hydroxy Groups

  摘要：

  DOI：

  10.1055/s-1984-31035

文献信息

• Indirect electrooxidation of alcohols by a double mediatory system with two redox couples of [R2N+:O]/R2NO.cntdot. and [Br.cntdot. or Br+]/Br- in an organic-aqueous two-phase solution
  作者：Tsutomu Inokuchi、Sigeaki Matsumoto、Sigeru Torii

  DOI：10.1021/jo00007a031

  日期：1991.3

  An indirect electrooxidation method for alcohol to aldehyde or ketone conversion has been developed. This method, applicable to chemoselective oxidation, employs two redox couples, consisting of 2,2,6,6-tetramethyl-piperidine-1-oxyl derivatives 6 and active bromine species. The former is required for the chemical process and recycled, whereas the latter is to be involved in the electrochemical process. Three chemical events play an important role in this system: (1) the formation of [Br or Br+] from bromide ion by discharge on the anode in an aqueous solution, (2) the reaction of N-oxyl compounds 6 with active bromine species to generate N-oxoammonium ion 7, and (3) the oxidation of alcohols with 7 in an organic phase. Optimum conditions were established as follows: an aqueous 25% NaBr solution buffered at pH 8.6 in a binary system, the use of 1-10 mol % of 4-(benzoyloxy)piperidine derivatives 6, and adjustment of an electric current at 10-100 mA/cm2. The successful applications of the present method to the oxidation of a variety of primary and secondary alcohols including 1,n-diols, giving the corresponding carbonyl compounds, have delineated its synthetic utility. The chemoselective oxidation of a primary hydroxy group in the presence of secondary one has been achieved with a high selectivity by the present procedure.
• Carbonyl Compounds by Osmium Tetroxide Oxidation: Preferential Oxidation of Primary over Secondary Hydroxy Groups
  作者：Anna Maria Maione、Aurelio Romeo

  DOI：10.1055/s-1984-31035

  日期：——