(4S,5R)-5-Tridecyl-4-(tris-phenylsulfanyl-methyl)-dihydro-furan-2-one | 1025911-12-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4S,5R)-5-Tridecyl-4-(tris-phenylsulfanyl-methyl)-dihydro-furan-2-one
• 英文别名: (4S,5R)-5-tridecyl-4-[tris(phenylsulfanyl)methyl]oxolan-2-one
• CAS: 1025911-12-9
• 化学式: C₃₆H₄₆O₂S₃
• 分子量: 606.958
• InChiKey: LKEARRHZKJHHEV-SZAHLOSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  41
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (4S,5R)-5-Tridecyl-4-(tris-phenylsulfanyl-methyl)-dihydro-furan-2-one 在 三氟化硼乙醚 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 水 为溶剂， 生成 (2R,3S,4S)-4-methyl-5-oxo-2-tridecyltetrahydrofuran-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：

  magnesium,dodecane,bromide 在 吡啶 、 正丁基锂 、 copper(I) bromide dimethylsulfide complex 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 苯 为溶剂， 生成 (4S,5R)-5-Tridecyl-4-(tris-phenylsulfanyl-methyl)-dihydro-furan-2-one
  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)].