(E)-3-butyl-4-pentylideneoxetan-2-one | 872631-12-4

• 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: (E)-3-butyl-4-pentylideneoxetan-2-one
• 英文别名: (4E)-3-butyl-4-pentylideneoxetan-2-one
• CAS: 872631-12-4
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: MJZLRAHODCHJCG-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (E)-3-butyl-4-pentylideneoxetan-2-one 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 2-Butyl-3-hydroxy-n-octanoic 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：

  己酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 以72%的产率得到(E)-3-butyl-4-pentylideneoxetan-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 method for the asymmetric synthesis of beta-lactone compounds
  申请人：Smith W. Jeffrey

  公开号：US20060258620A1

  公开（公告）日：2006-11-16

  The present invention features methods of treating a cancer in a subject by administering an effective amount of a beta-lactone to the subject. The invention also features methods of inhibiting angiogenesis in a subject by administering an effective amount of an inhibitor of fatty acid synthase to the subject. These methods can be used to treat a variety of cancers and other diseases and conditions. The invention also features methods of identifying beta-lactones and other compounds that can be used in the methods of the invention for the treatment of tumors, inhibition of angiogenesis, and the treatment of diseases and conditions that involve pathological angiogenesis. The invention also features methods of synthesizing beta-lactones and features novel beta-lactone compounds.

  本发明涉及通过向患者施用有效量的β-内酰胺来治疗患者身上的癌症的方法。本发明还涉及通过向患者施用脂肪酸合成酶抑制剂的有效量来抑制患者身上的血管生成的方法。这些方法可以用于治疗各种癌症和其他疾病和病况。本发明还涉及识别β-内酰胺和其他化合物的方法，这些化合物可以用于本发明中用于治疗肿瘤、抑制血管生成以及治疗涉及病理性血管生成的疾病和病况的方法。本发明还涉及合成β-内酰胺的方法和新型β-内酰胺化合物的特点。
• US7728153B2
  申请人：——

  公开号：US7728153B2

  公开（公告）日：2010-06-01
• 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.