(+)-(3R,4R,5R)-3-hexadecyl-4-hydroxy-5-methyldihydro-2(3H)-furanone | 159855-46-6

• 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: (+)-(3R,4R,5R)-3-hexadecyl-4-hydroxy-5-methyldihydro-2(3H)-furanone
• 英文别名: (2R,3R,4R)-2-Hexadecyl-3-hydroxy-4-methyl-γ-butyrolactone；(3R,4R,5R)-3-hexadecyl-4-hydroxy-5-methyloxolan-2-one
• CAS: 159855-46-6
• 化学式: C₂₁H₄₀O₃
• 分子量: 340.547
• InChiKey: RUZVORNWDRKUFJ-AQNXPRMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  24
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (+)-(3R,4R,5R)-3-hexadecyl-4-hydroxy-5-methyldihydro-2(3H)-furanone 以 吡啶 为溶剂， 反应 24.0h， 以93%的产率得到(+)-(3R,4R,5R)-3-hexadecyl-4-O-acetyl-5-methyldihydro-2(3H)-furanone
  参考文献：
  名称：

  对映体合成的三取代丁内酯天然产物及其类似物。

  摘要：

  已经开发出合成对映体纯形式的高度取代的丁内酯的通用方法。描述了该方法在高效合成内酯天然产物blastmycinone（1），NFX-2（2），antimycinone（3）和NFX-4（4）以及两种脂质代谢物（5，6）中的应用。另外，还描述了5-表胚芽孢霉素（22），5-表-NFX-2（21b），5-表-NFX-4（21c）和脂质代谢产物类似物（19、20）的总合成。目标分子的总产率是迄今为止文献中报道的最高。

  DOI：

  10.1021/jo961171i
• 作为产物：
  描述：

  (R)-N-Benzyl-N-methyl-3-hydroxy-4-pentenamide 在 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 lithium diisopropyl amide 作用下， 以 乙二醇二甲醚 、 水 、 甲苯 为溶剂， 反应 42.0h， 生成 (+)-(3R,4R,5R)-3-hexadecyl-4-hydroxy-5-methyldihydro-2(3H)-furanone
  参考文献：
  名称：

  New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-.gamma.-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds

  摘要：

  A new synthesis of all four isomeric 3-hydroxy-4-methyl-gamma-butyrolactones (11, ent-11, 12, ent-12) has been performed. The former two were prepared via stereoselective iodolactonization, which favors the cis-3,4-disubstituted system (16a and ent-16a), of N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-13, readily available by resolution of the racemate by lipase-mediated transesterification; and the latter two were prepared via stereoselective oxylactonization, which favors the trans-3,4-disubstituted system [(3R,4S)-20a and ent-(3R,4S)-20a], of O-TBDMS-protected N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-14. Butyrolactones 11 and 12 have been readily transformed into biologically active compounds [(-)-blastmycinolactol (27), (-)-NFX-2 (2), (-)-NFX-4 (3), lipid metabolites 9 and 10, and the sex pheromone (-)-(2S,3S)-2,3-octanediol (30)].

  DOI：

  10.1021/jo00103a008

文献信息

• New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-.gamma.-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds
  作者：Hiroki Takahata、Yasuhiro Uchida、Takefumi Momose

  DOI：10.1021/jo00103a008

  日期：1994.12

  A new synthesis of all four isomeric 3-hydroxy-4-methyl-gamma-butyrolactones (11, ent-11, 12, ent-12) has been performed. The former two were prepared via stereoselective iodolactonization, which favors the cis-3,4-disubstituted system (16a and ent-16a), of N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-13, readily available by resolution of the racemate by lipase-mediated transesterification; and the latter two were prepared via stereoselective oxylactonization, which favors the trans-3,4-disubstituted system [(3R,4S)-20a and ent-(3R,4S)-20a], of O-TBDMS-protected N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-14. Butyrolactones 11 and 12 have been readily transformed into biologically active compounds [(-)-blastmycinolactol (27), (-)-NFX-2 (2), (-)-NFX-4 (3), lipid metabolites 9 and 10, and the sex pheromone (-)-(2S,3S)-2,3-octanediol (30)].
• Enantiospecific Synthesis of Trisubstituted Butyrolactone Natural Products and Their Analogs
  作者：Mukund P. Sibi、Jianliang Lu、Chelsy L. Talbacka

  DOI：10.1021/jo961171i

  日期：1996.1.1

  A general methodology for the synthesis of highly substituted butyrolactones in enantiomerically pure form has been developed. The application of this process in a highly efficient synthesis of lactone natural products blastmycinone (1), NFX-2 (2), antimycinone (3), and NFX-4 (4) and two lipid metabolites (5, 6) are described. Additionally, the total synthesis of 5-epi-blastmycinone (22), 5-epi-NFX-2

  已经开发出合成对映体纯形式的高度取代的丁内酯的通用方法。描述了该方法在高效合成内酯天然产物blastmycinone（1），NFX-2（2），antimycinone（3）和NFX-4（4）以及两种脂质代谢物（5，6）中的应用。另外，还描述了5-表胚芽孢霉素（22），5-表-NFX-2（21b），5-表-NFX-4（21c）和脂质代谢产物类似物（19、20）的总合成。目标分子的总产率是迄今为止文献中报道的最高。