10-氯-9-羟基十八烷酸甲酯 | 10411-46-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 10-氯-9-羟基十八烷酸甲酯
• 英文名称: methyl 10-chloro-9-hydroxyoctadecanoate
• 英文别名: 10-Chlor-9-hydroxystearinsaeuremethylester；Methyl-10,9-chlorhydroxystearat
• CAS: 10411-46-8
• 化学式: C₁₉H₃₇ClO₃
• 分子量: 348.954
• InChiKey: KVDWBNHMIIEJKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-9,10-epoxyoctadecanoic acid methyl ester 在 三甲基氯硅烷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 10-氯-9-羟基十八烷酸甲酯 、 9-氯-10-羟基十八烷酸甲酯
  参考文献：
  名称：

  Rauf, Abdul; Ahmad, Shabana, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1924 - 1928

  摘要：

  DOI：

文献信息

• Synthesis of hydroxyfatty esters by sequential epoxidation-hydrogenolysis: Solvent effects
  作者：Vicente Dorado、Clara I. Herrerías、José M. Fraile

  DOI：10.1016/j.apcata.2021.118270

  日期：2021.8

  to incompatibility problems with the impurities present or generated in the used solvents. The chlorinated impurities in α,α,α-trifluorotoluene leads to the formation of important amounts of chlorohydrins by HCl formation in the hydrogenolysis step. The use of trifluoroethanol (TFE) in the epoxidation step produces trifluoroacetic acid traces by oxidation, responsible for the opening of the epoxide

  由于所用溶剂中存在或产生的杂质的不相容性问题，不饱和脂肪酸酯的环氧化和氢解的串联/顺序组合并不简单。α,α,α-三氟甲苯中的氯化杂质通过氢解步骤中的 HCl 形成导致大量氯代醇的形成。在环氧化步骤中使用三氟乙醇 (TFE) 通过氧化产生痕量三氟乙酸，负责用水和 TFE 打开环氧化物。最终选择的溶剂是乙酸异丁酯，它具有所需的物理化学性质，在连续过程中从油酸甲酯中产生 85% 的羟基硬脂酸酯。
• Synthesis of Chloro Alkoxy and Alkoxy Derivatives of Methyl Oleate
  作者：Benjamin A. Lowery、Brad Andersh、Terry A. Isbell

  DOI：10.1007/s11746-013-2224-1

  日期：2013.6

  AbstractVegetable oil based lubricants typically have improved lubricity and biodegradability over their mineral oil based counterparts. However, vegetable oil lubricants often fail to meet the performance standards of mineral based oils with respect to cold temperature and resistance to oxidation. Olefins are an oxidatively weak point for vegetable based compounds. Removal of the olefin in a vegetable based lubricant through functionalization may increase resistance to oxidation. If the added functionality also causes branching of the alkyl chain, cold temperature properties may be improved. Any chemical modifications considered must be scalable and cost‐effective to be useful in a commercial application. In this study, methyl oleate was functionalized into a chloro alkoxy derivative. Sodium hypochlorite (household bleach) and calcium hypochlorite were both used to generate hypochlorous acid in situ. Hypochlorous acid and a series of alcohols (methanol, ethanol, and butanol) were reacted with methyl oleate to make chloro alkoxy compounds in 29.8–77.9 % yields. In an effort to make a branched saturated ether we removed the chlorine moiety of the chloro alkoxy compounds. Dehalogenation was achieved under basic conditions over a Pd/C catalyst in 2‐propanol. Reaction times increased substantially as the size of the adjacent alkoxy group increased. The reaction rate could be improved by heating the reactions above 100 °C in a pressure reactor. Increased reaction temperature also resulted in an increase in ketone side products from the competing elimination reactions. Saturated ether yields were 4.1–43.2 %.
• GUPTA, RANJANA;HASAN, S. Q.;AMAD, E.;AHMAD, M. S.;OSMAN, S. M., INDIAN J. CHEM., 1985, 23, N 7, 615-619
  作者：GUPTA, RANJANA、HASAN, S. Q.、AMAD, E.、AHMAD, M. S.、OSMAN, S. M.

  DOI：——

  日期：——
• Rauf, Abdul; Ahmad, Shabana, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1924 - 1928
  作者：Rauf, Abdul、Ahmad, Shabana

  DOI：——

  日期：——