3-Hexyl-4-septyloxetan-2-one | 872631-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-Hexyl-4-septyloxetan-2-one
• 英文别名: 4-heptyl-3-hexyloxetan-2-one
• CAS: 872631-18-0
• 化学式: C₁₆H₃₀O₂
• 分子量: 254.413
• InChiKey: HWFDGUZNEOXCSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Hexyl-4-septyloxetan-2-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以90%的产率得到2-hexyl-3-hydroxydecanoic acid
  参考文献：
  名称：

  霉菌酸生物表面活性剂的合成及其物理和表面活性

  摘要：

  AbstractFive mycolic acids [2‐alkyl‐3‐hydroxy FA: R1C*(OH)C*HR2COOH] were synthesized using acyl chlorides with alkyl chains of different lengths (total carbon numbers of mycolic acids, 12, 16, 20, 24, 36). The relationship between the chemical structures of the mycolic acids and their surface‐active properties was determined. The acids were synthesized in three steps: (i) dimerization of acyl chloride into alkyl ketene dimer, (ii) selective reduction of C=C to C‐C by hydrogenation, and (iii) β‐lactone ring cleavage under alkaline conditions. The yields of C12‐, C16‐, C20‐, C24‐, and C36‐mycolic acid were 72, 73, 73, 73, and 73%, respectively. The critical micelle concentrations (CMC) of C12‐, C16‐, and C20‐mycolic acid were 2.2×10−4, 1.36×10−4, and 7.4×10−5 M, respectively. As the carbon number increased, the surface tension at the CMC value was also lower; the values for C12‐, C16‐ and C20‐mycolic acid were 46.54, 43.59, and 41.57 dyn/cm, respectively. The emulsifying activities of mycolic acids were determined for n‐tetradecane, n‐hexadecane, cyclohexane, and diesel oil. The results showed that C12‐mycolic acid was the best emulsifier for diesel oil, C16‐mycolic acid was the best emulsifier for n‐tetradecane and n‐hexadecane, and C20‐mycolic acid was the best emulsifier for cyclohexane. This study showed that mycolic acids having, surface‐active properties can be chemically synthesized for potential applications in the detergent/cleaning material industries, for example, in oil spill cleanup, oil recovery, textiles, pharmaceuticals, and cosmetics.

  DOI：

  10.1007/s11746-005-5170-8
• 作为产物：
  描述：

  (E)-4-heptylidene-3-hexyloxetan-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以90%的产率得到3-Hexyl-4-septyloxetan-2-one
  参考文献：
  名称：

  霉菌酸生物表面活性剂的合成及其物理和表面活性

  摘要：

  AbstractFive mycolic acids [2‐alkyl‐3‐hydroxy FA: R1C*(OH)C*HR2COOH] were synthesized using acyl chlorides with alkyl chains of different lengths (total carbon numbers of mycolic acids, 12, 16, 20, 24, 36). The relationship between the chemical structures of the mycolic acids and their surface‐active properties was determined. The acids were synthesized in three steps: (i) dimerization of acyl chloride into alkyl ketene dimer, (ii) selective reduction of C=C to C‐C by hydrogenation, and (iii) β‐lactone ring cleavage under alkaline conditions. The yields of C12‐, C16‐, C20‐, C24‐, and C36‐mycolic acid were 72, 73, 73, 73, and 73%, respectively. The critical micelle concentrations (CMC) of C12‐, C16‐, and C20‐mycolic acid were 2.2×10−4, 1.36×10−4, and 7.4×10−5 M, respectively. As the carbon number increased, the surface tension at the CMC value was also lower; the values for C12‐, C16‐ and C20‐mycolic acid were 46.54, 43.59, and 41.57 dyn/cm, respectively. The emulsifying activities of mycolic acids were determined for n‐tetradecane, n‐hexadecane, cyclohexane, and diesel oil. The results showed that C12‐mycolic acid was the best emulsifier for diesel oil, C16‐mycolic acid was the best emulsifier for n‐tetradecane and n‐hexadecane, and C20‐mycolic acid was the best emulsifier for cyclohexane. This study showed that mycolic acids having, surface‐active properties can be chemically synthesized for potential applications in the detergent/cleaning material industries, for example, in oil spill cleanup, oil recovery, textiles, pharmaceuticals, and cosmetics.

  DOI：

  10.1007/s11746-005-5170-8

文献信息

• NOVEL LIPASE INHIBITORS, REPORTER SUBSTRATES AND USES THEREOF
  申请人：Northeastern University

  公开号：US20150099800A1

  公开（公告）日：2015-04-09

  The invention provides for novel lipase inhibitors, and compositions and devices comprising the same. The invention further provides for methods for treatment of disorders comprising administration of novel diacylglycerol lipase inhibitors, and compositions and devices comprising said inhibitors. In some embodiments, the disorders are pancreatitis, obesity, shock or pancreatic necrosis. The invention further provides for novel ether lipid reporter compounds and methods of assaying enzymatic activity comprising contacting a compound with a novel ether lipid reporter compound.

  本发明提供了新型脂肪酶抑制剂，以及包含它们的组合物和装置。本发明还提供了治疗疾病的方法，包括给予新型二酰基甘油脂肪酶抑制剂、含有该抑制剂的组合物和装置。在某些实施例中，这些疾病包括胰腺炎、肥胖症、休克或胰腺坏死。本发明还提供了新型醚脂质报告化合物和测定酶活性的方法，其中将化合物与新型醚脂质报告化合物接触。
• [EN] NOVEL LIPASE INHIBITORS, REPORTER SUBSTRATES AND USES THEREOF<br/>[FR] NOUVEAUX INHIBITEURS DE LIPASE, SUBSTRATS RAPPORTEURS ET LEURS UTILISATIONS
  申请人：UNIV NORTHEASTERN

  公开号：WO2013177492A2

  公开（公告）日：2013-11-28

  The invention provides for novel lipase inhibitors, and compositions and devices comprising the same. The invention further provides for methods for treatment of disorders comprising administration of novel diacylglycerol lipase inhibitors, and compositions and devices comprising said inhibitors. In some embodiments, the disorders are pancreatitis, obesity, shock or pancreatic necrosis. The invention further provides for novel ether lipid reporter compounds and methods of assaying enzymatic activity comprising contacting a compound with a novel ether lipid reporter compound.
• Synthesis of mycolic acid biosurfactants and their physical and surface-active properties
  作者：Myungjin Lee、Hyung Sub Gwak、Byeong Deog Park、Sung-Taik Lee

  DOI：10.1007/s11746-005-5170-8

  日期：2005.3

  AbstractFive mycolic acids [2‐alkyl‐3‐hydroxy FA: R1C*(OH)C*HR2COOH] were synthesized using acyl chlorides with alkyl chains of different lengths (total carbon numbers of mycolic acids, 12, 16, 20, 24, 36). The relationship between the chemical structures of the mycolic acids and their surface‐active properties was determined. The acids were synthesized in three steps: (i) dimerization of acyl chloride into alkyl ketene dimer, (ii) selective reduction of C=C to C‐C by hydrogenation, and (iii) β‐lactone ring cleavage under alkaline conditions. The yields of C12‐, C16‐, C20‐, C24‐, and C36‐mycolic acid were 72, 73, 73, 73, and 73%, respectively. The critical micelle concentrations (CMC) of C12‐, C16‐, and C20‐mycolic acid were 2.2×10−4, 1.36×10−4, and 7.4×10−5 M, respectively. As the carbon number increased, the surface tension at the CMC value was also lower; the values for C12‐, C16‐ and C20‐mycolic acid were 46.54, 43.59, and 41.57 dyn/cm, respectively. The emulsifying activities of mycolic acids were determined for n‐tetradecane, n‐hexadecane, cyclohexane, and diesel oil. The results showed that C12‐mycolic acid was the best emulsifier for diesel oil, C16‐mycolic acid was the best emulsifier for n‐tetradecane and n‐hexadecane, and C20‐mycolic acid was the best emulsifier for cyclohexane. This study showed that mycolic acids having, surface‐active properties can be chemically synthesized for potential applications in the detergent/cleaning material industries, for example, in oil spill cleanup, oil recovery, textiles, pharmaceuticals, and cosmetics.