4-methyl-5-methoxy-2(5H)-furanone | 19957-75-6

• 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-methoxy-2(5H)-furanone
• 英文别名: 4-methyl-5-methoxyfuran-2(5H)-one；4-metil-5-metoxi-2(5H)-furanona；5-methoxy-4-methyl-2(5H)-furanone；5-Methoxy-4-methylfuran-2(5H)-one；2-methoxy-3-methyl-2H-furan-5-one
• CAS: 19957-75-6
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: BAMVMNHALWMMNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-5-methoxy-2(5H)-furanone 在 盐酸 、 ammonium hydroxide 作用下， 反应 1.33h， 生成 4-methyl-5-methoxy-3-pyrrolin-2-one
  参考文献：
  名称：

  Farina, Francisco; Martin, M. Victoria; Paredes, M. Carmen, Heterocycles, 1984, vol. 22, # 8, p. 1733 - 1739

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aS,4R,6aR)-4-Methoxy-3,3a,4,6a-tetrahydro-furo[3,4-c]pyrazol-6-one 以 乙基苯 、 乙酸乙酯 、 乙腈 为溶剂， 反应 12.0h， 生成 4-methyl-5-methoxy-2(5H)-furanone
  参考文献：
  名称：

  Farina, F.; Martin, M. V.; Soria, M. L., Anales de Quimica, 1995, vol. 91, # 1-2, p. 65 - 73

  摘要：

  DOI：

文献信息

• Asymmetric 1,3-dipolar cycloadditions to 5-(R)-menthyloxy-2(5H)-furanone
  作者：Minze T. Rispens、Erik Keller、Ben de Lange、Robert W.J. Zijlstra、Ben L. Feringa

  DOI：10.1016/0957-4166(94)80023-5

  日期：1994.4

  Various diazo compounds, nitrile oxides, nitrones and azomethine ylides were examined in 1,3-dipolar cycloadditions to enantiomerically pure 5-(R)-menthyloxy-2(5H)-furanone 1a. Pyrazoline 9 was obtained in 100% c.y. as a mixture of 2 diastereoisomers in ratios up to 72 : 28, whereas pyrazoline 16 was obtained in 100% c.y. as a single enantiomer. Photochemically pyrazolines 9 and 10 have been converted to cyclopropanes 11 and 13. Under thermal conditions pyrazoline 9 is converted to 4-methyl-5-menthyloxy-2(5H)-furanone. Isoxazoles 21a-24a were obtained enantiomerically pure via nitrile oxide addition to la in 64-67% yield. Nitrone addition afforded isoxazolidines 27, 28 and 34 with complete anti-facial- and regiochemistry, but with endo-exo selectivities up to 76%. Enantiomerically pure isoxazolidines were obtained in 25-75% yield. Pyrrolidine 36 was obtained diastereomerically pure in 81% c.y. Pyrrolidines 42 and 45, however, were obtained as diastereomeric mixtures in 37% resp. 6% yield.
• Chiral induction in photochemical reactions - 15.
  作者：Norbert Hoffmann、Helmut Buschmann、Gerhard Raabe、Hans-Dieter Scharf

  DOI：10.1016/s0040-4020(01)89419-9

  日期：1994.1

  The mechanism of the diastereoselection in the photosensitized [2 + 2]-cycloaddition reaction of ethylene to 5-alkoxy-2(5H)-furanones is investigated. The dependence of product ratio on the reaction temperature as well as on structural features of the enone system is measured. The structure dependent activation parameter differences (Delta Delta H-#, Delta Delta S-#) obtained by this method (modified Eyring plot) are used as a tool to characterize the stereoelectronic factors, which are responsible for the diastereoselection. In detail these factors involve: pyramidalization of the beta-carbon, homoanomeric effect, and the steric requirements of the alkoxy substituent in the relaxed ((3) pi pi*)-excited furanones.
• Farina, Francisco; Martin, Victoria M.; Sanchez, Felix, Heterocycles, 1986, vol. 24, # 9, p. 2587 - 2592
  作者：Farina, Francisco、Martin, Victoria M.、Sanchez, Felix

  DOI：——

  日期：——
• Pseudoesters and Derivatives. XXXI¹. Synthesis of 5-Ethylthio-, 5-Ethylsulfinyl- and 5-Ethylsulfonylfuran-2(5<i>H</i>)-ones
  作者：Francisco Fariña、M. Victoria Martín、Rosa M. Martín-Aranda、Ana Martínez de Guereñu

  DOI：10.1080/00397919308009801

  日期：1993.2

  Convenient syntheses of 5-(ethylthio)furan-2(5H)-ones 2a-k from the appropriate 5-methoxyfuran-2(5H)-one 1a-g are described. The oxidation to the corresponding sulfoxides 5a-c and sulfones 6a-f is also reported.
• FARINA, F.;MARTIN, M. V.;PAREDES, M. C.;ORTEGA, M. C.;TITO, A., HETEROCYCLES, 1984, 22, N 8, 1733-1739
  作者：FARINA, F.、MARTIN, M. V.、PAREDES, M. C.、ORTEGA, M. C.、TITO, A.

  DOI：——

  日期：——