<1-²H>-1-octyl camphanoate | 62057-71-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: <1-²H>-1-octyl camphanoate
• 英文别名: (1S)-<1-2H>octyl (-)-camphanate；[(1S)-1-deuteriooctyl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
• CAS: 62057-71-0
• 化学式: C₁₈H₃₀O₄
• 分子量: 311.426
• InChiKey: BRPHBCMMZJWDOU-LQWQELGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  <1-²H>-octanal 在 吡啶 作用下， 反应 50.5h， 生成 <1-²H>-1-octyl camphanoate
  参考文献：
  名称：

  Micellar effects in the nitrous acid deamination reaction of (R)-[1-2H]-1-octanamine

  摘要：

  The nitrous acid deamination of 1-octanamine (1) afforded mixtures of isomeric octenes, octanols, and octyl nitrites. The aggregation of 1.HClO4 in micelles induced the formation of dioctyl ethers and of 1-nitrooctane as additional products. In homogeneous solution (submicellar aqueous conditions or HOAc), [1-H-2]-1-octanol was obtained from [1-H-2]-1 with ca. 95% inversion of configuration. Above the critical micelle concentration, the enantiomeric purity of [1-H-2]-1-octanol decreased while [1-H-2]-1-nitrooctane was formed with ca.90% retention of configuration. 1-Octyl..NO2 radical pairs, rather than ion pairs, are likely to intervene on the retentive route to 1-nitrooctane and 1-octyl nitrite. Equilibration, via NO exchange, of (R)-[1-H-2]-1-octyl nitrite with the more abundant (S)-[1-H-2]-1-octanol is thought to account for the diminished ee of both products.

  DOI：

  10.1021/jo00057a025

文献信息

• Micellar effects in the nitrous acid deamination reaction of (R)-[1-2H]-1-octanamine
  作者：Daniel Brosch、Wolfgang Kirmse

  DOI：10.1021/jo00057a025

  日期：1993.2

  The nitrous acid deamination of 1-octanamine (1) afforded mixtures of isomeric octenes, octanols, and octyl nitrites. The aggregation of 1.HClO4 in micelles induced the formation of dioctyl ethers and of 1-nitrooctane as additional products. In homogeneous solution (submicellar aqueous conditions or HOAc), [1-H-2]-1-octanol was obtained from [1-H-2]-1 with ca. 95% inversion of configuration. Above the critical micelle concentration, the enantiomeric purity of [1-H-2]-1-octanol decreased while [1-H-2]-1-nitrooctane was formed with ca.90% retention of configuration. 1-Octyl..NO2 radical pairs, rather than ion pairs, are likely to intervene on the retentive route to 1-nitrooctane and 1-octyl nitrite. Equilibration, via NO exchange, of (R)-[1-H-2]-1-octyl nitrite with the more abundant (S)-[1-H-2]-1-octanol is thought to account for the diminished ee of both products.