7-甲基辛酸

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维基百科，自由的百科全书
7-甲基辛酸
英文名 7-Methyloctanoic acid
识别
CAS号 693-19-6  checkY
SMILES
 
  • CC(C)CCCCCC(O)=O
性质
化学式 C9H18O2
摩尔质量 158.24 g·mol⁻¹
密度 0.919±0.06 g·cm−3[1]
熔点 3—5 °C（276—278 K）[2]
沸点 248 °C（521 K）（765 Torr）[3]
溶解性（水） 0.11 g[1]
pKa 4.78±0.10[1]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

7-甲基辛酸是一种有机化合物，化学式为C9H18O2，它是异壬酸（德语：Isononansäure）的同分异构体之一。[4]

制备

7-甲基辛酸可由7-甲基辛醇和吡啶重铬酸盐（或三氧化铬[2]）的氧化反应制得。[5]6-溴己酸钠和异丙基氯化镁反应，酸化后加水可以析出7-甲基辛酸。[6]

7-甲基辛酸甲酯在碱性条件下水解[7]，或7-甲基-7-辛烯酸在钯碳的催化下由氢气还原，也能得到产物。[8]

性质

7-甲基辛酸和光气加热反应，得到7-甲基辛酰氯；[9]在酸性催化剂的催化下，也能和醇反应生成酯。[10][11]

参考文献

  1. ^ 1.0 1.1 1.2 Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2020 ACD/Labs). Retrieved from SciFinder. [2020-07-25].
  2. ^ 2.0 2.1 Klimentová, Jana; Kosák, Petr; Vávrová, Kateřina; Holas, Tomáš; Hrabálek, Alexandr. Influence of terminal branching on the transdermal permeation-enhancing activity in fatty alcohols and acids. Bioorganic & Medicinal Chemistry. 2006, 14 (23): 7681–7687. ISSN 0968-0896. doi:10.1016/j.bmc.2006.08.013. 
  3. ^ Levene, P. A.; Allen, C. H. The oxidation of branched-chain fatty acids. I. The action of hydrogen peroxide on the homologs of isobutyric acid. Journal of Biological Chemistry, 1916. 27: 433-462. ISSN: 0021-9258.
  4. ^ Isononansäure Nr.276. (PDF) (PDF). Berufsgenossenschaft Rohstoffe und chemische Industrie (BG RCI). 2010 [2020-07-25]. （原始内容存档 (PDF)于2016-03-24）. 
  5. ^ Cooper, Matthew; Blaskovich, Mark; Alejandra, Gallardo-Goday; Hansford, Karl; Elliott, Alysha. Peptide antibiotics. 2019. WO 2019084628 A1.
  6. ^ Thiel, Verena; Kunze, Brigitte; Verma, Pankaj; Wagner-Döbler, Irene; Schulz, Stefan. New Structural Variants of Homoserine Lactones in Bacteria. ChemBioChem. 2009, 10 (11): 1861–1868. ISSN 1439-4227. doi:10.1002/cbic.200900126. 
  7. ^ Riclea, Ramona; Aigle, Bertrand; Leblond, Pierre; Schoenian, Ilka; Spiteller, Dieter; Dickschat, Jeroen S. Volatile Lactones from Streptomycetes Arise via the Antimycin Biosynthetic Pathway. ChemBioChem. 2012, 13 (11): 1635–1644. ISSN 1439-4227. doi:10.1002/cbic.201200260. 
  8. ^ Cui, A-Long; Hu, Xin-Xin; Gao, Yan; Jin, Jie; Yi, Hong; Wang, Xiu-Kun; Nie, Tong-Ying; Chen, Yang; He, Qi-Yang; Guo, Hui-Fang; Jiang, Jian-Dong; You, Xue-Fu; Li, Zhuo-Rong. Synthesis and Bioactivity Investigation of the Individual Components of Cyclic Lipopeptide Antibiotics. Journal of Medicinal Chemistry. 2018, 61 (5): 1845–1857. ISSN 0022-2623. doi:10.1021/acs.jmedchem.7b01367. 
  9. ^ Lan, Xingfen; Qiu, Xuenan; Peng, Jiuhe. Process for preparation of acyl chloride compounds. 2016. CN 105585478 A.
  10. ^ Springer, Helmut; Merscher, Klaus-Dieter; Heumueller, Rudolf; Schimmer, Klaus; Strutz, Heinz. Process for the production of glycol-carboxylate ester plasticizers with the azeotropic distillative removal of process water. 2001. DE 19940991 A1.
  11. ^ Mun, Dasom; Vo, Anh Thi Hoang; Kim, Bora; Shul, Yong-Gun; Cho, Jin Ku. Solventless esterification of fatty acids with trimethylolpropane using sulfonated amorphous carbons derived from wood powder. Catalysis Communications. 2017, 96: 32–36. ISSN 1566-7367. doi:10.1016/j.catcom.2017.03.015. 
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