(4R,5R)-4-hydroxy-5-[(E)-oct-1-enyl]dihydrofuran-2(3H)-one | 1402043-94-0

• 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: (4R,5R)-4-hydroxy-5-[(E)-oct-1-enyl]dihydrofuran-2(3H)-one
• 英文别名: (4R,5R)-4-hydroxy-5-((E)-oct-1-en-1-yl)dihydrofuran-2(3H)-one；(4R,5R)-4-hydroxy-5-[(E)-oct-1-enyl]oxolan-2-one
• CAS: 1402043-94-0
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: SYAQBJGCGJDLFQ-QSNNZYTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (4R,5R)-4-hydroxy-5-[(E)-oct-1-enyl]dihydrofuran-2(3H)-one 在 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 碳酸氢钠 作用下， 以 乙腈 、 苯 为溶剂， 反应 9.0h， 生成 (3aR,5R,6aR)-5-hexylperhydrofuro-[3,2-b]furan-2-one
  参考文献：
  名称：

  A Protecting-Group-Free Synthesis of Hagen’s Gland Lactones

  摘要：

  A practical protecting group free synthesis of Hagen's gland lactones 1 and 2 is accomplished in four steps and 25.6 and 37.4% overall yields, respectively. The strategy relies on a one-pot conversion of D-glucono-delta-lactone to beta-hydroxy-gamma-vinyl-gamma-lactone, cross-metathesis, and iodocyclization-deiodinization as key steps.

  DOI：

  10.1021/jo301465z
• 作为产物：
  描述：

  葡萄糖酸内酯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 17.0h， 生成 (4R,5R)-4-hydroxy-5-[(E)-oct-1-enyl]dihydrofuran-2(3H)-one
  参考文献：
  名称：

  A Protecting-Group-Free Synthesis of Hagen’s Gland Lactones

  摘要：

  A practical protecting group free synthesis of Hagen's gland lactones 1 and 2 is accomplished in four steps and 25.6 and 37.4% overall yields, respectively. The strategy relies on a one-pot conversion of D-glucono-delta-lactone to beta-hydroxy-gamma-vinyl-gamma-lactone, cross-metathesis, and iodocyclization-deiodinization as key steps.

  DOI：

  10.1021/jo301465z

文献信息

• Concise Stereoselective Synthesis of β-Hydroxy-γ-lactones: (4<i>R</i>,5<i>R</i>)-4-Hydroxy-γ-decalactone from the Japanese Orange Fly and Enantiomers of Arachnid Harvestmen Isolates
  作者：Ashvin J. Gangani、Praveen Kumar、Rodney A. Fernandes

  DOI：10.1021/acs.jnatprod.0c01207

  日期：2021.1.22

  The naturally occurring (4R,5R)-4-hydroxy-γ-decalactone from the Japanese orange fly and the antipode of (4S,5R)-4-hydroxy-γ-dodecalactone from the harvestmen arachnid and their stereoisomers are synthesized from the chiral pool material d-glucono-δ-lactone in a few steps. The one-pot conversion of the latter to γ-vinyl-β-hydroxy-γ-lactone, cross-metathesis with requisite olefin, and hydrogenation

  来自日本橙蝇的天然存在的 (4 R ,5 R )-4-羟基-γ-十内酯和来自收割机蛛形纲动物的 (4 S ,5 R )-4-羟基-γ-十二内酯及其立体异构体是由手性池材料d-葡萄糖酸-δ-内酯分几步合成。后者的一锅转化为γ-乙烯基-β羟基- γ内酯，交叉复分解以必要的烯烃和氢化启用的合成顺式内酯在短短的两锅操作。γ-乙烯基-β-羟基-γ-内酯的额外有效Pd催化烯丙基异构化导致高产率的抗-内酯。
• A Protecting-Group-Free Synthesis of Hagen’s Gland Lactones
  作者：Rodney A. Fernandes、Pullaiah Kattanguru

  DOI：10.1021/jo301465z

  日期：2012.10.19

  A practical protecting group free synthesis of Hagen's gland lactones 1 and 2 is accomplished in four steps and 25.6 and 37.4% overall yields, respectively. The strategy relies on a one-pot conversion of D-glucono-delta-lactone to beta-hydroxy-gamma-vinyl-gamma-lactone, cross-metathesis, and iodocyclization-deiodinization as key steps.