2,5-dimethyl-2-phenyl-3(2H)-furanone | 133255-53-5

• 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: 2,5-dimethyl-2-phenyl-3(2H)-furanone
• 英文别名: 2,5-dimethyl-2-phenylfuran-3-one
• CAS: 133255-53-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: VLVRWYWSWZZGKT-UHFFFAOYSA-N

物化性质

• 沸点：
  100-102 °C(Press: 0.08 Torr)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2,5-dimethyl-2-phenyl-3(2H)-furanone 在 甲基磺酰氯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 5.0h， 生成 2-methyl-2-phenyl-5-vinyl-3(2H)-furanone
  参考文献：
  名称：

  New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity

  摘要：

  A convenient route to new 3(2H)-furanones is described through hydrogenolysis and subsequent acidic hydrolysis of isoxazoles. The antiproliferative activity of title compounds were evaluated against leukemia-, carcinoma-, neuroblastoma-, and sarcoma-derived human cell lines in comparison to the natural compound geiparvarin. The structure activity relationship indicated that the maximum in vitro antiproliferative activity correlates with the presence of a heterocyclic ring on the ethenyl moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00776-2
• 作为产物：
  描述：

  5-hydroxy-5-phenyl-3-hexyn-2-one 在 氯[三(对三氟甲基苯基)膦]金(I) 、 silver trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以94%的产率得到2,5-dimethyl-2-phenyl-3(2H)-furanone
  参考文献：
  名称：

  阳离子金（I）催化的γ-羟基炔酮分子内环化为3（2 H）-呋喃酮

  摘要：

  （p -CF 3 C 6 H 4）3 PAuCl和AgOTf的组合为在温和条件下易于获得的γ-羟基炔酮的分子内环化生成了强大的催化剂。取代的3（2 H）-呋喃酮的产率为55-94％。该方法也适用于制备2，3-二氢-4 H-吡喃-4-酮。

  DOI：

  10.1021/jo100048j

文献信息

• Anti-ulcer 5-(2-substituted ethenyl)-3-(2H)-furanones
  申请人：American Home Products Corporation

  公开号：US04966905A1

  公开（公告）日：1990-10-30

  A compound of the formula: ##STR1## in which R is alkyl, phenyl or halophenyl; R.sup.2 is substituted phenyl having from 1 to 3 substituents selected from halo, alkyl, alkylthio, alkylsulfonyl, cyano, trifluoromethyl, or R.sup.2 is pyridinyl, pyrazinyl, quinolinyl, N-alkylpyrrolyl, thienyl, benzothienyl, or furyl; and n is 1 or 2, are cytoprotective anti-ulcer agents.

  化合物的公式为：##STR1## 其中 R 是烷基，苯基或卤代苯基；R.sup.2 是被取代的苯基，其有 1 到 3 个取代基，选自卤素，烷基，硫代烷基，磺酰基烷基，氰基，三氟甲基，或 R.sup.2 是吡啶基，吡嗪基，喹啉基，N-烷基吡咯基，噻吩基，苯并噻吩基或呋喃基；n 是 1 或 2，是细胞保护性抗溃疡剂。
• Anti-ulcer 5-(2-substituted ethenyl)-3(2H)-furanones
  申请人：American Home Products Corporation

  公开号：US05001126A1

  公开（公告）日：1991-03-19

  A compound of the formula: ##STR1## in which R is alkyl, phenyl or halophenyl; R.sup.2 is substituted phenyl having from 1 to 3 substituents selected from halo, alkyl, alkylthio, alkylsulfonyl, cyano, trifluoromethyl, or R.sup.2 is pyridinyl, pyrazinyl, quinolinyl, N-alkylpyrrolyl, thienyl, benzothienyl, or furyl; and n is 1 or 2, are cytoprotective anti-ulcer agents.

  化合物的公式为：##STR1## 其中R是烷基，苯基或卤代苯基; R.sup.2是取代苯基，其取代基从卤，烷基，烷基硫醇，烷基磺酰，氰，三氟甲基中选择1到3个，或R.sup.2是吡啶基，吡嗪基，喹啉基，N-烷基吡咯基，噻吩基，苯并噻吩基或呋喃基; n为1或2，是细胞保护的抗溃疡剂。
• Synthesis and antiulcer activity of novel 5-(2-ethenyl substituted)-3(2H)-furanones
  作者：Steven W. Felman、Ivo Jirkovsky、Kevin A. Memoli、Luis Borella、Cheryl Wells、Jim Russell、Jim Ward

  DOI：10.1021/jm00085a003

  日期：1992.4

  In order to investigate new antiulcer agents, spizofurone 1 (AG-629) was fragmented and reassembled to generate 5-phenyl-2,2-dimethyl-3(2H)-furanone (bullatenone, 2). Because of the antiulcer activity of 2,5-phenyl-substituted 2,2-dimethyl-3(2H)-furanones (3-6) were made and shown to have poor activity. Insertion of an ethenyl link between the furanone and phenyl rings gave 5-(2-phenylethenyl)-2,2-dimethyl-3(2H)-furanone (7). This compound had better activity than 2. Compounds 8-41 were synthesized to evaluate the SAR in 5-(2-ethenyl substituted)-3(2H)-furanones. Electron-withdrawing substituents on the aromatic ring (8, 10, 19, and 20) gave 2-3-fold higher activity. Further increases in the activity were found when the phenyl ring was replaced by heterocyclic nuclei. Compounds that contained a thiophene (29), pyridine (24-26), or quinoline ring (32) had the best activity. Replacement of the methyl group on the furanone ring with a phenyl (34) or p-fluorophenyl (40) substituent in the 2-pyridine series gave compounds with activity that ranked with the best obtained in this study. The best compounds from the above SAR studies were evaluated in the ethanol-necrosis model for duration of cytoprotection action. Compounds 19, 24, and 29, which had the best duration of action, were tested with AG-629 in the acidified aspirin and indomethacin-induced lesion models. Only compound 24 had equivalent activity with AG-629 in both models.
• Natural and synthetic geiparvarins are strong and selective MAO-B inhibitors. synthesis and SAR studies
  作者：Angelo Carotti、Antonio Carrieri、Stefano Chimichi、Marco Boccalini、Barbara Cosimelli、Carmela Gnerre、Andrea Carotti、Pierre-Alain Carrupt、Bernard Testa

  DOI：10.1016/s0960-894x(02)00798-9

  日期：2002.12

  Natural geiparvarin 1 and a number of its analogues were prepared and tested as inhibitors of both monoamine oxidase isoforms, MAO-B and MAO-A. The desmethyl congener 6 of geiparvarin, proved potent and selective MAO-B inhibitor (PIC50 = 7.55 vs 4.62). X-ray crystallography and molecular modelling studies helped the understanding of the observed structure-activity relationships. (C) 2002 Elsevier Science Ltd. All rights reserved.
• PROCESS FOR CONVERTING PROPARGYLIC AMINE-N-OXIDES TO ENAMINONES
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP1000012A1

  公开（公告）日：2000-05-17