4-Nonyl-3-octyl-oxetan-2-one | 872631-19-1

• 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: 4-Nonyl-3-octyl-oxetan-2-one
• 英文别名: 4-nonyl-3-octyloxetan-2-one
• CAS: 872631-19-1
• 化学式: C₂₀H₃₈O₂
• 分子量: 310.521
• InChiKey: WKNLQRMGJHHPFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  4-Nonyl-3-octyl-oxetan-2-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以90%的产率得到2-octyl-3-hydroxydodecanoic 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：

  癸酰氯 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 生成 4-Nonyl-3-octyl-oxetan-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

• BIOLOGICAL PRODUCTION OF ß-LACTONES
  申请人：Regents of the University of Minnesota

  公开号：US20200048668A1

  公开（公告）日：2020-02-13

  Methods of using β-lactone biosynthetic enzyme genes and host cells expressing one or more of those genes, e.g., heterologous expression, are provided.
• 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.