(5R)-5-undecyl-2,5-dihydro-2-furanone | 157497-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (5R)-5-undecyl-2,5-dihydro-2-furanone
• 英文别名: (R)-5-Undecyl-2(5H)-furanone；(2R)-2-undecyl-2H-furan-5-one
• CAS: 157497-27-3
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: UBLAYGKBWFACNF-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R)-5-undecyl-2,5-dihydro-2-furanone 在 4-二甲氨基吡啶 、 正丁基锂 、 三氟化硼乙醚 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 45.0h， 生成 (3S,4S,5R)-4-(Benzyloxycarbonyl)-3-methyl-5-undecyl-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
• 作为产物：
  描述：

  Decylmagnesium bromide 在 吡啶 、 copper(I) bromide dimethylsulfide complex 、 氨 作用下， 以 甲醇 、 苯 为溶剂， 生成 (5R)-5-undecyl-2,5-dihydro-2-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

• Stereoselective Synthesis of (+)-Nephrosteranic Acid by Ring-Closing Metathesis and Its Biological Evaluation
  作者：Arun Kumar Perepogu、D. Raman、U. S. N. Murty、Vaidya Jayathirtha Rao

  DOI：10.1080/00397910903011337

  日期：2010.2.12

  A simple and efficient approach to (+)-nephrosteranic acid from dodecanol as a starting material is described, employing Sharpless asymmetric epoxidation, ring-closing metathesis, and Gilman addition of a vinyl group as key steps. These key reactions allow fast access to trisubstituted γ-butyrolactone. The molecule synthesized exhibits potent antifungal, antibacterial, and cytotoxic activities against

  描述了一种以十二烷醇为原料制备 (+)-肾甾烷酸的简单而有效的方法，采用 Sharpless 不对称环氧化、闭环复分解和吉尔曼加成乙烯基作为关键步骤。这些关键反应可以快速获得三取代的 γ-丁内酯。合成的分子对所有测试菌株均表现出有效的抗真菌、抗菌和细胞毒性活性。
• 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.
• 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)].