(+)-(3S,4R,5S)-3-hexadecyl-4-hydroxy-5-methylbutanolide | 796122-60-6

• 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: (+)-(3S,4R,5S)-3-hexadecyl-4-hydroxy-5-methylbutanolide
• 英文别名: (3S,4R,5S)-3-hexadecyl-4-hydroxy-5-methyloxolan-2-one
• CAS: 796122-60-6
• 化学式: C₂₁H₄₀O₃
• 分子量: 340.547
• InChiKey: RUZVORNWDRKUFJ-UFYCRDLUSA-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：

  (+)-(3S,4R,5S)-3-hexadecyl-4-hydroxy-5-methylbutanolide 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.0h， 生成 (4S)-2-hexadecanyl-4-methylbut-2-enolide
  参考文献：
  名称：

  Donor–Acceptor Substituted Cyclopropane to Butanolide and Butenolide Natural Products: Enantiospecific First Total Synthesis of (+)-Hydroxyancepsenolide

  摘要：

  An oxygen substituted donoracceptor cyclopropane (DAC) is used as a common intermediate in the enantiospecific collective total synthesis of butanolide- and butenolide-based natural products like (+)-juruenolide C and D, (+)-blastmycinone, (+)-antimycinone, and (+)-ancepsenolide. Enantiospecific first total syntheses of (+)-hydroxyancepsenolide and its acetate are achieved confirming their absolute stereochemistry.

  DOI：

  10.1021/ol503246k
• 作为产物：
  描述：

  (3aS,6S,6aR)-4-methoxy-6-methyltetrahydrofuro[3,4-b]furan-2(3H)-one 在 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 氢气 、 二异丁基氢化铝 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 4.92h， 生成 (+)-(3S,4R,5S)-3-hexadecyl-4-hydroxy-5-methylbutanolide
  参考文献：
  名称：

  Donor–Acceptor Substituted Cyclopropane to Butanolide and Butenolide Natural Products: Enantiospecific First Total Synthesis of (+)-Hydroxyancepsenolide

  摘要：

  An oxygen substituted donoracceptor cyclopropane (DAC) is used as a common intermediate in the enantiospecific collective total synthesis of butanolide- and butenolide-based natural products like (+)-juruenolide C and D, (+)-blastmycinone, (+)-antimycinone, and (+)-ancepsenolide. Enantiospecific first total syntheses of (+)-hydroxyancepsenolide and its acetate are achieved confirming their absolute stereochemistry.

  DOI：

  10.1021/ol503246k

文献信息

• ¹³C NMR-Based Empirical Rules to Determine the Configuration of Fatty Acid Butanolides. Novel γ-Dilactones from <i>Pterogorgia</i> spp
  作者：Manuel Lorenzo、Inmaculada Brito、Mercedes Cueto、Luis D'Croz、José Darias

  DOI：10.1021/ol061572c

  日期：2006.10.1

  Diastereomeric gamma-dilactones isolated from Pterogorgia spp allowed the establishment of C-13 NMR-based empirical rules to determine the relative stereochemistry of 3-alkyl-4-hydroxy-5-methyl-2(5H)-dihydrofuranones, gamma-lactone moieties ubiquitous in many bioactive synthetic and natural products. An NMR-based method using Pirkle's reagent at low temperature allowed the absolute configuration of the naturally occurring dibutenolides to be unambiguously determined. A biogenetic pathway that involves oxidation of long-chain (C16:0 and C18:0) fatty acids is proposed.
• Donor–Acceptor Substituted Cyclopropane to Butanolide and Butenolide Natural Products: Enantiospecific First Total Synthesis of (+)-Hydroxyancepsenolide
  作者：Santosh J. Gharpure、Laxmi Narayan Nanda、Manoj Kumar Shukla

  DOI：10.1021/ol503246k

  日期：2014.12.19

  An oxygen substituted donoracceptor cyclopropane (DAC) is used as a common intermediate in the enantiospecific collective total synthesis of butanolide- and butenolide-based natural products like (+)-juruenolide C and D, (+)-blastmycinone, (+)-antimycinone, and (+)-ancepsenolide. Enantiospecific first total syntheses of (+)-hydroxyancepsenolide and its acetate are achieved confirming their absolute stereochemistry.