(S)-3-tetradecyl-5-methyl-2(5H)-furanone | 120046-79-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-tetradecyl-5-methyl-2(5H)-furanone
• 英文别名: 5(S)-3-tetradecyl-5-methyl-2(5H)-furanone；(2S)-2-methyl-4-tetradecyl-2H-furan-5-one
• CAS: 120046-79-9
• 化学式: C₁₉H₃₄O₂
• 分子量: 294.478
• InChiKey: CFTGKTJNVTWXNK-KRWDZBQOSA-N

物化性质

• 沸点：
  416.0±14.0 °C(Predicted)
• 密度：
  0.911±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  棕榈酸甲酯 在 三乙胺 、 三氟乙酸酐 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-3-tetradecyl-5-methyl-2(5H)-furanone
  参考文献：
  名称：

  Straightforward Synthesis of Two Pairs of Enantiomeric Butenolides 3-Tetradecyl- and 3-Hexadecyl-5-methyl-2(5 H )-furanone

  摘要：

  Based on the synthetic method of optically active 3-alkyl-5-methyl-2(5H)-furanones from lactic acid, two pairs of chiral butenolides 3-tetradecyl- and 3-hexadecyl-5-methyl-2(5H)-furanone have been straightforwardly synthesized from methyl stearate and methyl palmitate respectively by aldol condensation with (R)- or (S)-O-tetrahydropyranyl lactal prepared from corresponding ethyl lactate and beta-elimination.

  DOI：

  10.1080/10242430212189

文献信息

• Stereocontrolled synthesis of (3,4,5)-3-alkyl-4-hydroxy-5-methyl-2(3)-dihydrofubanones and derivatives
  作者：Rosa M. Ortuño、Joaquim Bigorra、Josep Font

  DOI：10.1016/s0040-4020(01)86019-1

  日期：1988.1

  Absolute and relative configuration has been assigned to some metabolites from mahuba tree and the coral , by enantio- and diastereo-controlled synthesis of (3,4,5)-3-alkyl-4-hydroxy-5-methyl-2(3)-dihydrofura-nones and their acetyl derivativatives, ()-lactic acid being used as chiral precursor.

  绝对和相对构型已被分配到从mahuba树和珊瑚一些代谢物，由对映和非对映控制合成（3 ，4 ，5 ）-3-烷基-4-羟基-5-甲基-2（3 ） -二氢呋喃酮及其乙酰基衍生物，（）-乳酸用作手性前体。
• Straightforward Synthesis of Two Pairs of Enantiomeric Butenolides 3-Tetradecyl- and 3-Hexadecyl-5-methyl-2(5 H )-furanone
  作者：Bu-Bing Zeng、Tai-Shan Hu、Wei Yun、Yikang Wu、Yu-Lin Wu

  DOI：10.1080/10242430212189

  日期：2002.3

  Based on the synthetic method of optically active 3-alkyl-5-methyl-2(5H)-furanones from lactic acid, two pairs of chiral butenolides 3-tetradecyl- and 3-hexadecyl-5-methyl-2(5H)-furanone have been straightforwardly synthesized from methyl stearate and methyl palmitate respectively by aldol condensation with (R)- or (S)-O-tetrahydropyranyl lactal prepared from corresponding ethyl lactate and beta-elimination.