4-methyl-5-butyl-2(5H)furanone | 126188-65-6

• 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: 4-methyl-5-butyl-2(5H)furanone
• 英文别名: 5-butyl-4-methylfuran-2(5H)-one；4-methyl-5-(n-butyl)-2(5H)-furanone；2-butyl-3-methyl-2H-furan-5-one
• CAS: 126188-65-6
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: RWXYSLDKSARYFF-UHFFFAOYSA-N

物化性质

• 沸点：
  264.9±9.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  4-methyl-5-butyl-2(5H)furanone 以5%的产率得到
  参考文献：
  名称：

  JEFFORD, CHARLES W.;SLEDESKI, ADAM W.;BOUKOUVALAS, JOHN, HELV. CHIM. ACTA, 72,(1989) N, C. 1362-1370

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-1-庚烯-3-醇 在 Grubbs catalyst first generation 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-methyl-5-butyl-2(5H)furanone
  参考文献：
  名称：

  Synthesis of α,β-Unsaturated 4,5-Disubstituted γ-Lactones via Ring-Closing Metathesis Catalyzed by the First-Generation Grubbs' Catalyst

  摘要：

  4-Methyl-5-alkyl-2(5H)-furanones have been prepared by ruthenium-catalyzed ring-closing metathesis of the suitable methallyl acrylates. Despite the electron deficiency of the conjugated double bond and of the gem-disubstitution of the allylic alkene moiety in the starting acrylates, the first-generation Grubbs' catalyst I proved to be an effective promoter for the ring closure, affording the expected butenolides in good to high yields.

  DOI：

  10.1021/ol0504087

文献信息

• An efficient synthesis of 2(5H)-furanone and furan derivatives using 3-(phenylthio)propenal as a 1,3-dipolar synthon.
  作者：Mitsuaki WATANABE、Masao TSUKAZAKI、Yoshiaki HIRAKAWA、Masatomo IWAO、Sunao FURUKAWA

  DOI：10.1248/cpb.37.2914

  日期：——

  Various 2(5H)-furanone and furan derivatives were synthesized from 3-(phenylthio)propenal by a one-pot process via carbonyl addition of a range of organometallic reagents and subsequent sulfide-directed α-lithiatin followed by electrophilic trapping. This methodology was successfuly applied to the syntheses of quercus lactone and 2, 5-diarylfuran natural products.

  通过一锅法工艺，通过一系列有机金属试剂的羰基加成，随后进行硫醚导向的α-锂化，并最终进行亲电捕获，从3-（苯硫基）丙烯醛合成了各种2（5H）-呋喃酮和呋喃衍生物。该方法成功应用于栎素和2,5-二芳基呋喃天然产物的合成。
• Synthesis of β-halobutenolides and their Pd(0)-catalyzed cross-coupling reactions with terminal alkynes and organozinc reagents. A general route to β-substituted butenolides and formal synthesis of cis-whisky lactone
  作者：Shengming Ma、Zhangjie Shi、Zhanqian Yu

  DOI：10.1016/s0040-4020(99)00726-7

  日期：1999.10

  procedure for the efficient synthesis of β-halobutenolides was developed. The Pd(0)-catalyzed coupling reactions of β-halobutenolides with terminal alkynes or organozinc reagents, i.e., 1-alkenyl, aryl, and alkyl zinc reagents, to afford β-substituted butenolides were carefully studied. Using the coupling protocol of γ-(n-butyl)-β-iodobutenolide with methylzinc halide, we performed an efficient formal synthesis

  开发了一种有效合成β-卤代丁烯内酯的改进方法。仔细研究了β-卤代丁烯内酯与末端炔烃或有机锌试剂（即1-烯基，芳基和烷基锌试剂）在Pd（0）催化下的偶联反应，得到β-取代的丁烯内酯。使用γ-（正丁基）-β-碘丁烯内酯与甲基卤化锌的偶联方案，我们进行了威士忌内酯的有效形式合成。
• Synthesis ofcis andtrans Whisky and Cognac lactones by the regiocontrolled alkylation of 2-(trimethylsiloxy)furan
  作者：Charles W. Jefford、Adam W. Sledeski、John Boukouvalas

  DOI：10.1002/hlca.19890720625

  日期：1989.9.20

  The racemic cis- and trans-5-butyltetrahydro-4-methylfuran-2-ones ( = whisky lactones) and their higher homologues tetrahydro-4-methyl-5-pentylfuran-2-ones ( = cognac lactones) have been prepared in 2–3 steps from 2-(trimethylsiloxy)furan. Regioselective alkylation of the latter afforded the 5-butyl- and 5-pentylfuran-2(5H)-ones which served as precursors for the stereocontrolled construction of either

  外消旋的顺式和反式-5-丁基四氢-4-甲基呋喃-2-酮（=威士忌内酯）及其高级同系物四氢-4-甲基-5-戊基呋喃-2-酮（=白兰地内酯）已在2中制备。从2-（三甲基甲硅烷氧基）呋喃中–3步。后者的区域选择性烷基化提供了5-丁基-和5-戊基呋喃-2（5 H）-一，它们用作饮料内酯的任一非对映异构体的立体控制结构的前体。还描述了这些5-烷基呋喃-2（5H）-一的重氮甲烷加合物的结构和互变异构。
• Yoda, Hidemi; Shirakawa, Koji; Takabe, Kunihiko, Chemistry Letters, 1989, p. 1391 - 1392
  作者：Yoda, Hidemi、Shirakawa, Koji、Takabe, Kunihiko

  DOI：——

  日期：——
• YODA, HIDEMI;SHIRAKAWA, KOJI;TAKABE, KUNIHIKO, CHEM. LETT.,(1989) N, C. 1391-1392
  作者：YODA, HIDEMI、SHIRAKAWA, KOJI、TAKABE, KUNIHIKO

  DOI：——

  日期：——