(E)-2,2-dimethyl-5-(2-phenylethenyl)-3(2H)-furanone | 110841-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2,2-dimethyl-5-(2-phenylethenyl)-3(2H)-furanone
• 英文别名: 2,2-dimethyl-5-[(E)-2-phenylethenyl]furan-3-one
• CAS: 110841-33-3
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: RDWFSLOZEJGVCE-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(3-甲基-5-异恶唑基)-2-丙醇 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 (E)-2,2-dimethyl-5-(2-phenylethenyl)-3(2H)-furanone
  参考文献：
  名称：

  Synthesis and antiulcer activity of novel 5-(2-ethenyl substituted)-3(2H)-furanones

  摘要：

  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.

  DOI：

  10.1021/jm00085a003

文献信息

• Cationic Gold(I)-Catalyzed Intramolecular Cyclization of γ-Hydroxyalkynones into 3(2<i>H</i>)-Furanones
  作者：Masahiro Egi、Kenji Azechi、Moriaki Saneto、Kaori Shimizu、Shuji Akai

  DOI：10.1021/jo100048j

  日期：2010.3.19

  The combination of (p-CF3C6H4)3PAuCl and AgOTf generates a powerful catalyst for the intramolecular cyclizations of readily available γ-hydroxyalkynones under mild conditions. The substituted 3(2H)-furanones are obtained in 55−94% yields. This method is also applicable to the preparation of 2,3-dihydro-4H-pyran-4-ones.

  （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。
• A new and facile synthesis of 3(2H)-furanones via carboxylation- decarboxylation sequence
  作者：Yoshio Inoue、Kunihiro Ohuchi、Shin Imaizumi

  DOI：10.1016/s0040-4039(00)82233-9

  日期：1988.1
• INOUE, YOSHIO;OHUCHI, KUNIHIRO;YEN, I. -FANG;IMAIZUMI, SHIN, BULL. CHEM. SOC. JAP., 62,(1989) N1, C. 3518-3522
  作者：INOUE, YOSHIO、OHUCHI, KUNIHIRO、YEN, I. -FANG、IMAIZUMI, SHIN

  DOI：——

  日期：——
• INOUE, YOSHIO;OHUCHI, KUNIHIRO;IMAIZUMI, SHIN, TETRAHEDRON LETT., 29,(1988) N 46, C. 5941-5942
  作者：INOUE, YOSHIO、OHUCHI, KUNIHIRO、IMAIZUMI, SHIN

  DOI：——

  日期：——
• US4966905A
  申请人：——

  公开号：US4966905A

  公开（公告）日：1990-10-30