4,5-Dihydro-2-methyl-5-oxofuran-3-carbonsaeuremethylester | 112799-48-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,5-Dihydro-2-methyl-5-oxofuran-3-carbonsaeuremethylester
• 英文别名: methyl 2-methyl-5-oxo-4,5-dihydrofuran-3-carboxylate；methyl 5-methyl-2-oxo-3H-furan-4-carboxylate
• CAS: 112799-48-1
• 化学式: C₇H₈O₄
• 分子量: 156.138
• InChiKey: GXNBFXVMIZWXRW-UHFFFAOYSA-N

物化性质

• 熔点：
  61-63 °C
• 沸点：
  306.3±35.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  色胺 、 4,5-Dihydro-2-methyl-5-oxofuran-3-carbonsaeuremethylester 在 (11bS)-4-羟基-2,6-二[2,4,6-三(异丙基)苯基]-二萘并[2,1-d:1',2'-f][1,3,2]二氧杂磷杂卓4-氧化物 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以65%的产率得到methyl 2-acetyl-4-{[2-(1H-indol-3-yl)ethyl]amino}-4-oxobutanoate
  参考文献：
  名称：

  Enantioselective Brønsted Acid-Catalyzed N-Acyliminium Cyclization Cascades

  摘要：

  An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(1)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol% bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.

  DOI：

  10.1021/ja9024885
• 作为产物：
  描述：

  2-Methyl-3-methoxycarbonyl-2,5-dimethoxy-2,5-dihydrofuran 以 溶剂黄146 为溶剂， 反应 0.17h， 以20%的产率得到4,5-Dihydro-2-methyl-5-oxofuran-3-carbonsaeuremethylester
  参考文献：
  名称：

  Eiden, Fritz; Grusdt, Ulrike, Archiv der Pharmazie, 1987, vol. 320, # 10, p. 1020 - 1031

  摘要：

  DOI：

文献信息

• New facile synthesis of furan-2(3H)-ones and 2,3,5-trisubstituted furans via intramolecular Wittig reaction of acid anhydride
  作者：Mei Sun、Qin Wan、Ming-Wu Ding

  DOI：10.1016/j.tet.2019.04.074

  日期：2019.6

  A new facile preparation of furan-2(3H)-ones and 2,3,5-trisubstituted furans by a sequential O-acylation/Wittig(/O-acylation) reaction has been developed. The easily accessible 2-(triphenylphosphoranylidene)-succinic acid 1-ester 3 reacted with acid chloride produced furan-2(3H)-ones 4 in good yields in the presence of DMAP via sequential O-acylation and intramolecular Wittig reaction of acid anhydride

  通过顺序的O-酰化/ Wittig（/ O-酰化）反应，开发了一种新的简便的呋喃-2（3 H）-酮和2,3,5-三取代呋喃的制备方法。在DMAP的作用下，通过顺序的O-酰化和酸酐的分子内Wittig反应，易得的2-（三苯基亚膦酰基）-琥珀酸1-酯3与酰氯反应，生成了呋喃-2（3 H）-ones 4，收率很高。。随后，在三乙胺存在下，通过进一步的O-酰化，由呋喃-2（3 H）-ones 4和各种芳基氯化物制备2,3,5-三取代的呋喃5。
• Unsaturated Lactones: Synthesis and Applications
  作者：Heshui Yu、Margaret M. Kayser

  DOI：10.1080/00397919408010159

  日期：1994.6

  Abstract An easy approach to the synthesis of substituted unsaturated lactones is described, and the reactions of these compounds with nucleophiles leading to the formation of useful intermediates are reported.

  摘要描述了一种合成取代不饱和内酯的简单方法，并报道了这些化合物与亲核试剂的反应导致有用中间体的形成。
• EIDEN, FRITZ;GRUSDT, ULRIKE, ARCH. PHARM., 320,(1987) N 10, 1020-1031
  作者：EIDEN, FRITZ、GRUSDT, ULRIKE

  DOI：——

  日期：——
• Enantioselective Brønsted Acid-Catalyzed <i>N</i>-Acyliminium Cyclization Cascades
  作者：Michael E. Muratore、Chloe A. Holloway、Adam W. Pilling、R. Ian Storer、Graham Trevitt、Darren J. Dixon

  DOI：10.1021/ja9024885

  日期：2009.8.12

  An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(1)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol% bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.
• Eiden, Fritz; Grusdt, Ulrike, Archiv der Pharmazie, 1987, vol. 320, # 10, p. 1020 - 1031
  作者：Eiden, Fritz、Grusdt, Ulrike

  DOI：——

  日期：——