(4S,6R)-4-methyl-6-pentyltetrahydro-2H-pyran-2-one | 1450804-77-9

• 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,6R)-4-methyl-6-pentyltetrahydro-2H-pyran-2-one
• 英文别名: (4S,6R)-4-methyl-6-pentyloxan-2-one
• CAS: 1450804-77-9
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: GHFLPVFPWUUIED-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (4S,6R)-4-methyl-6-pentyltetrahydro-2H-pyran-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  (4S,6R)-4-methyl-6-pentyltetrahydro-2H-pyran-2-one as an efficient intermediate in the preparation of chiral building blocks with methyl-branched carbon skeleton. Application to the synthesis of bioactive compounds

  摘要：

  Synthesis was performed of (3S)-3-methyldecen-1-ol and (4S)-4-methylundecen-1-ol, chiral alcohols with a methyl-branched carbon skeleton. The possibility of their application in asymmetric syntheses of insect pheromones was demonstrated.

  DOI：

  10.1134/s1070428014110141
• 作为产物：
  描述：

  (6R)-4-methyl-6-pentyl-5,6-dihydro-2H-pyran-2-one 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 、 硼酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以98%的产率得到(4S,6R)-4-methyl-6-pentyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Methyl (5R)-5-hydroxy-3-methylidenedecanoate as a promising building block in asymmetric syntheses of bioactive natural compounds

  摘要：

  Simple and efficient asymmetric syntheses of several lactones with the use of methyl (5R)-5-hydroxy-3-methylidenedecanoate as a polyfunctional building block are described.

  DOI：

  10.1134/s107042801307004x

文献信息

• α,β-Unsaturated β-Methyl-δ-lactones in Nitrile Oxide Cycloaddition Reactions. Synthesis of Saturated Lactones and Lactams
  作者：I. V. Mineyeva

  DOI：10.1134/s1070428022060033

  日期：2022.6

  Abstract New isoxazoline derivatives have been synthesized in high yields by cycloaddition of acetonitrile oxide to α,β-unsaturated β-methyl-δ-lactones. These unsaturated lactones have been used to obtain β-methyl branched saturated lactones and lactams, as well as lactones with an inversed configuration of hydroxy group, following the divergent approach.

  摘要 通过将氧化乙腈环加成到 α,β-不饱和 β-甲基-δ-内酯上，以高收率合成了新的异恶唑啉衍生物。这些不饱和内酯已被用于获得β-甲基支链饱和内酯和内酰胺，以及具有反相羟基构型的内酯，遵循发散的方法。