ethyl 9-acetoxynonanoate | 71715-56-5

• 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: ethyl 9-acetoxynonanoate
• 英文别名: 9-Acetoxy-nonansaeure-ethylester；8-Ethoxycarbonyloctanolacetat；Ethyl 9-(acetyloxy)nonanoate；ethyl 9-acetyloxynonanoate
• CAS: 71715-56-5
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: ODBHRTPVNVDWLL-UHFFFAOYSA-N

物化性质

• 沸点：
  305.6±25.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 9-acetoxynonanoate 生成 8-壬烯酸
  参考文献：
  名称：

  Avramenko,V.G. et al., Journal of general chemistry of the USSR, 1962, vol. 32, p. 1095 - 1098

  摘要：

  DOI：
• 作为产物：
  描述：

  8-乙氧羰基辛醇 、 乙酸酐 在 sodium acetate 作用下， 反应 2.0h， 以50%的产率得到ethyl 9-acetoxynonanoate
  参考文献：
  名称：

  ω-羟基壬酸及其酯衍生物的制备

  摘要：

  AbstractMethyl ricinoleate was ozonized in methanol or in acetic acid and the intermediate hydroperoxides were reduced electrochemically on Pb‐cathode to give 9‐hydroxynonanoic acid 1 in high yields. The acid 1 was also prepared by direct castor oil ozonolysis in methanol followed by sodium borohydride reduction of the intermediate hydroperoxides. The cost of the electricity for the electroreduction was at least 30 times lower as compared with sodium borohydride consumption. 9‐Hydroxynonanoic acid was then transformed to alkyl 9‐acetoxynonanoates 3a–3d, for which 1H nuclear magnetic reasonance, mass, and infrared spectra are given. Esterification of the hydroxy acid 1 with boric acid and pyrolysis of the resultant orthoborates produced 8‐nonenoic acid 4 in a 45% yield. Reaction of 4 with lower aliphatic alcohols in presence of Amberlyst 15 produced alkyl 8‐noneates 5a–5d along with some amounts of a cis/trans mixture of alkyl 7‐noneates.

  DOI：

  10.1007/s11746-999-0070-y

文献信息

• Cross-coupling between functionalized alkylcopper reagents and functionalized alkyl halides
  作者：Charles E. Tucker、Paul Knochel

  DOI：10.1021/jo00070a003

  日期：1993.8

  Functionalized dialkylzincs treated with Me2Ci(CN)(MgCl)2 in DMPU undergo highly chemoselective cross-coupling reactions with functionalized alkyl iodides or benzylic bromides providing polyfunctional products in good to excellent yields.
• Avramenko,V.G. et al., Journal of general chemistry of the USSR, 1962, vol. 32, p. 1095 - 1098
  作者：Avramenko,V.G. et al.

  DOI：——

  日期：——
• Preparation of ω-hydroxynonanoic acid and its ester derivatives
  作者：Jozef Kula、Krzysztof Smigielski、Thuat B. Quang、Iwona Grzelak、Magdalena Sikora

  DOI：10.1007/s11746-999-0070-y

  日期：1999.7

  AbstractMethyl ricinoleate was ozonized in methanol or in acetic acid and the intermediate hydroperoxides were reduced electrochemically on Pb‐cathode to give 9‐hydroxynonanoic acid 1 in high yields. The acid 1 was also prepared by direct castor oil ozonolysis in methanol followed by sodium borohydride reduction of the intermediate hydroperoxides. The cost of the electricity for the electroreduction was at least 30 times lower as compared with sodium borohydride consumption. 9‐Hydroxynonanoic acid was then transformed to alkyl 9‐acetoxynonanoates 3a–3d, for which 1H nuclear magnetic reasonance, mass, and infrared spectra are given. Esterification of the hydroxy acid 1 with boric acid and pyrolysis of the resultant orthoborates produced 8‐nonenoic acid 4 in a 45% yield. Reaction of 4 with lower aliphatic alcohols in presence of Amberlyst 15 produced alkyl 8‐noneates 5a–5d along with some amounts of a cis/trans mixture of alkyl 7‐noneates.