(4S,5S)-4-hydroxy-5-methyl-3-(13'-tetradecenyl)dihydrofuran-2(3H)-one | 1253852-61-7

• 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: (4S,5S)-4-hydroxy-5-methyl-3-(13'-tetradecenyl)dihydrofuran-2(3H)-one
• CAS: 1253852-61-7
• 化学式: C₁₉H₃₄O₃
• 分子量: 310.477
• InChiKey: AKIGJXYMTYZQMP-PXKIYYGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  22.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-hydroxy-5-methyl-3-(13'-tetradecenyl)dihydrofuran-2(3H)-one 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis of solamin type mono-THF acetogenins using cross-metathesis

  摘要：

  The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.028
• 作为产物：
  描述：

  13-tetradecen-1-yl iodide 、 (4RS,5RS)-4-hydroxy-5-methyldihydrofuran-2(3H)-one 在 sodium hexamethyldisilazane 、 盐酸 、 水 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 0.5h， 以80%的产率得到(4S,5S)-4-hydroxy-5-methyl-3-(13'-tetradecenyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis of solamin type mono-THF acetogenins using cross-metathesis

  摘要：

  The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.028