(4R,5S)-4--5-pentyl-4,5-dihydro-2(3H)-furanone | 165605-80-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4R,5S)-4--5-pentyl-4,5-dihydro-2(3H)-furanone
• 英文别名: (4R,5S)-5-pentyl-4-[tris(phenylsulfanyl)methyl]oxolan-2-one
• CAS: 165605-80-1
• 化学式: C₂₈H₃₀O₂S₃
• 分子量: 494.743
• InChiKey: VTODGMLPBZUNKA-FTJBHMTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4--5-pentyl-4,5-dihydro-2(3H)-furanone 在 三氟化硼乙醚 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以84%的产率得到(2S,3R)-(-)-5-oxo-2-pentyltetrahydrofuran-3-carboxylic acid
  参考文献：
  名称：

  Concise Syntheses of Natural .gamma.-Butyrolactones, (+)-trans-Whisky Lactone, (+)-trans-Cognac Lactone, (-)-Methylenolactocin, (+)-Nephrosteranic Acid, and (+)-Roccellaric Acid Using Novel Chiral Butenolide Synthons

  摘要：

  cis-4-Hydroxy-5-(iodomethyl)-4,5-dihydro-2(3H)-furanones (1 and ent-1) were converted by cross-coupling with several Grignard-derived cuprates followed by benzoylation and base-induced elimination into new chiral butenolides 12, 14, ent-14, 20, and 27. The sequential conjugate addition-quenching of these butenolides under complete stereocontrol provided several polysubstituted gamma-butyrolactones including flavor components [(+)-trans-whisky lactone (3) and (+)-trans-cognac lactone (4)], the antitumor antibiotic lactone (-)-methylenolactocin (5), and lichen components [(+)-nephrosteranic acid (7) and (+)-roccellaric acid (8)].

  DOI：

  10.1021/jo00122a051
• 作为产物：
  描述：

  (4S,5S)-4,5-dihydro-4-hydroxy-5-pentyl-2-(3H)-furanone 在 吡啶 、 正丁基锂 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 苯 为溶剂， 反应 4.0h， 生成 (4R,5S)-4--5-pentyl-4,5-dihydro-2(3H)-furanone
  参考文献：
  名称：

  Concise Syntheses of Natural .gamma.-Butyrolactones, (+)-trans-Whisky Lactone, (+)-trans-Cognac Lactone, (-)-Methylenolactocin, (+)-Nephrosteranic Acid, and (+)-Roccellaric Acid Using Novel Chiral Butenolide Synthons

  摘要：

  cis-4-Hydroxy-5-(iodomethyl)-4,5-dihydro-2(3H)-furanones (1 and ent-1) were converted by cross-coupling with several Grignard-derived cuprates followed by benzoylation and base-induced elimination into new chiral butenolides 12, 14, ent-14, 20, and 27. The sequential conjugate addition-quenching of these butenolides under complete stereocontrol provided several polysubstituted gamma-butyrolactones including flavor components [(+)-trans-whisky lactone (3) and (+)-trans-cognac lactone (4)], the antitumor antibiotic lactone (-)-methylenolactocin (5), and lichen components [(+)-nephrosteranic acid (7) and (+)-roccellaric acid (8)].

  DOI：

  10.1021/jo00122a051

文献信息

• Concise Syntheses of Natural .gamma.-Butyrolactones, (+)-trans-Whisky Lactone, (+)-trans-Cognac Lactone, (-)-Methylenolactocin, (+)-Nephrosteranic Acid, and (+)-Roccellaric Acid Using Novel Chiral Butenolide Synthons
  作者：Hiroki Takahata、Yasuhiro Uchida、Takefumi Momose

  DOI：10.1021/jo00122a051

  日期：1995.9

  cis-4-Hydroxy-5-(iodomethyl)-4,5-dihydro-2(3H)-furanones (1 and ent-1) were converted by cross-coupling with several Grignard-derived cuprates followed by benzoylation and base-induced elimination into new chiral butenolides 12, 14, ent-14, 20, and 27. The sequential conjugate addition-quenching of these butenolides under complete stereocontrol provided several polysubstituted gamma-butyrolactones including flavor components [(+)-trans-whisky lactone (3) and (+)-trans-cognac lactone (4)], the antitumor antibiotic lactone (-)-methylenolactocin (5), and lichen components [(+)-nephrosteranic acid (7) and (+)-roccellaric acid (8)].