(4R,5R)-5-Butyl-4-hydroxy-4,5-dihydro-2(3H)-furanone | 157497-25-1

• 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)-5-Butyl-4-hydroxy-4,5-dihydro-2(3H)-furanone
• 英文别名: (4R,5R)-5-butyl-4-hydroxyoxolan-2-one
• CAS: 157497-25-1
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: QETSTGPUGQREBA-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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)-5-Butyl-4-hydroxy-4,5-dihydro-2(3H)-furanone 在 吡啶 、 氨 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 (+)-反式威士忌内酯
  参考文献：
  名称：

  New entry to chiral butenolide synthons. Application to expeditious syntheses of (+)-nephrosteranic acid, (+)-trans-whisky lactone, and (+)-trans-cognac lactone

  摘要：

  A new envy to chiral butenolide synthons starting with iodolactonization of the readily available, homochiral N-benzyl-N-methyl-3-hydroxy-4-pentenamid (1) and its application to the syntheses of (+)-nephrosteranic acid (5), (+)-trans-whisky lactone (6), and (+)-trans-cognac lactone (7) are described.

  DOI：

  10.1016/s0040-4039(00)73129-7
• 作为产物：
  描述：

  (R)-N-Benzyl-N-methyl-3-hydroxy-4-pentenamide 在 碘 、 copper(I) bromide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 生成 (4R,5R)-5-Butyl-4-hydroxy-4,5-dihydro-2(3H)-furanone
  参考文献：
  名称：

  New entry to chiral butenolide synthons. Application to expeditious syntheses of (+)-nephrosteranic acid, (+)-trans-whisky lactone, and (+)-trans-cognac lactone

  摘要：

  A new envy to chiral butenolide synthons starting with iodolactonization of the readily available, homochiral N-benzyl-N-methyl-3-hydroxy-4-pentenamid (1) and its application to the syntheses of (+)-nephrosteranic acid (5), (+)-trans-whisky lactone (6), and (+)-trans-cognac lactone (7) are described.

  DOI：

  10.1016/s0040-4039(00)73129-7

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)].
• Synthesis of Optically Active Butenolides andγ-Lactones by the Sharpless Asymmetric Dihydroxylation ofβ,γ-Unsaturated Carboxylic Esters
  作者：Christian Harcken、Reinhard Brückner

  DOI：10.1002/anie.199727501

  日期：1997.1.7
• New entry to chiral butenolide synthons. Application to expeditious syntheses of (+)-nephrosteranic acid, (+)-trans-whisky lactone, and (+)-trans-cognac lactone
  作者：Hiroki Takahata、Yasuhiro Uchida、Takefumi Momose

  DOI：10.1016/s0040-4039(00)73129-7

  日期：1994.6

  A new envy to chiral butenolide synthons starting with iodolactonization of the readily available, homochiral N-benzyl-N-methyl-3-hydroxy-4-pentenamid (1) and its application to the syntheses of (+)-nephrosteranic acid (5), (+)-trans-whisky lactone (6), and (+)-trans-cognac lactone (7) are described.