12-oxododecanoic acid oxime | 91694-67-6

• 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: 12-oxododecanoic acid oxime
• 英文别名: 12-Hydroxyiminododecanoic acid
• CAS: 91694-67-6
• 化学式: C₁₂H₂₃NO₃
• 分子量: 229.32
• InChiKey: ZQZAHAISYUWEFD-UHFFFAOYSA-N

物化性质

• 沸点：
  400.8±18.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-oxododecanoic acid oxime 在 哌啶 、 nickel diacetate 作用下， 以 xylene 为溶剂， 反应 24.0h， 以45%的产率得到12-amino-12-oxododecanoic acid
  参考文献：
  名称：

  藜芦酸合成12-氨基十二烷酸和11-氨基十一烷酸

  摘要：

  Abstract12‐Aminododecanoic acid and 11‐aminoundecanoic acid, monomer precursors for nylon‐12 and nylon‐11, respectively, have been synthesized from vernolic (cis‐12,13‐epoxy‐cis‐9‐octadecenoic) acid via a reaction sequence that includes the formation of 12‐oxododecanoic acid oxime. Saponification of vernonia oil, followed by a low‐temperature recrystallization at −20°C, gave 51% vernolic acid (97% purity, m.p. 23–25°C). Hydrogenation afforded cis‐12,13‐epoxystearic acid (m.p. 52–54°C, lit. m.p. 52–54°C), which upon oxidation with periodic acid in tertiary butyl alcohol gave 12‐oxododecanoic acid with an isolated yield of 71.0%. Reaction of the oxoacid with hydroxylamine hydrochloride gave 12‐oxododecanoic acid oxime, which was catalytically reduced to give 12‐aminododecanoic acid with a yield greater than 85% and a melting point of 184–186°C (lit. m.p. 185–187°C). 11‐Aminoundecanoic acid was prepared from the 12‐oxododecanoic acid oxime via a three‐step reaction sequence that involved a Beckmann rearrangement, Hofmann degradation, and hydrolysis. Thus, the aldoxime acid was hydrolyzed in the presence of nickel acetate tetrahydrate to give 11‐carbamoylundecanoic acid (48% yield, m.p. 129–131°C, lit. m.p. 129–130°C). The amide was then treated with a solution of sodium methoxide and bromine at 70–80°C to give 11‐(methoxycarbonylamino)undecanoic acid at 75% yield (m.p. 84–86°C; elemental analysis, calculated for C13H25NO4: C, 60.19; H, 9.73; N, 5.40; O, 24.68%; found C, 60.02; H, 9.81; N, 5.26; O, 24.91%), which upon alkaline hydrolysis and subsequent neutralization gave 11‐aminoundecanoic acid at 34% yield (m.p. 189–192°C, lit. m.p. 190°C). Mass spectrometric and 13C nuclear magnetic resonance data of the previously unreported 11‐(methoxycarbonylamino)undecanoic acid is provided.

  DOI：

  10.1007/s11746-997-0176-z
• 作为产物：
  描述：

  (+/-)-顺式-12,13-环氧-9(Z)-十八碳烯酸 在 platinum(IV) oxide sodium hydroxide 、 盐酸羟胺 、 氢气 、 过碘酸 作用下， 以 甲醇 、 乙醇 、 水 、 叔丁醇 为溶剂， 100.0 ℃ 、303.98 kPa 条件下， 反应 5.92h， 生成 12-oxododecanoic acid oxime
  参考文献：
  名称：

  藜芦酸合成12-氨基十二烷酸和11-氨基十一烷酸

  摘要：

  Abstract12‐Aminododecanoic acid and 11‐aminoundecanoic acid, monomer precursors for nylon‐12 and nylon‐11, respectively, have been synthesized from vernolic (cis‐12,13‐epoxy‐cis‐9‐octadecenoic) acid via a reaction sequence that includes the formation of 12‐oxododecanoic acid oxime. Saponification of vernonia oil, followed by a low‐temperature recrystallization at −20°C, gave 51% vernolic acid (97% purity, m.p. 23–25°C). Hydrogenation afforded cis‐12,13‐epoxystearic acid (m.p. 52–54°C, lit. m.p. 52–54°C), which upon oxidation with periodic acid in tertiary butyl alcohol gave 12‐oxododecanoic acid with an isolated yield of 71.0%. Reaction of the oxoacid with hydroxylamine hydrochloride gave 12‐oxododecanoic acid oxime, which was catalytically reduced to give 12‐aminododecanoic acid with a yield greater than 85% and a melting point of 184–186°C (lit. m.p. 185–187°C). 11‐Aminoundecanoic acid was prepared from the 12‐oxododecanoic acid oxime via a three‐step reaction sequence that involved a Beckmann rearrangement, Hofmann degradation, and hydrolysis. Thus, the aldoxime acid was hydrolyzed in the presence of nickel acetate tetrahydrate to give 11‐carbamoylundecanoic acid (48% yield, m.p. 129–131°C, lit. m.p. 129–130°C). The amide was then treated with a solution of sodium methoxide and bromine at 70–80°C to give 11‐(methoxycarbonylamino)undecanoic acid at 75% yield (m.p. 84–86°C; elemental analysis, calculated for C13H25NO4: C, 60.19; H, 9.73; N, 5.40; O, 24.68%; found C, 60.02; H, 9.81; N, 5.26; O, 24.91%), which upon alkaline hydrolysis and subsequent neutralization gave 11‐aminoundecanoic acid at 34% yield (m.p. 189–192°C, lit. m.p. 190°C). Mass spectrometric and 13C nuclear magnetic resonance data of the previously unreported 11‐(methoxycarbonylamino)undecanoic acid is provided.

  DOI：

  10.1007/s11746-997-0176-z