5-methyl-5-styrylfuran-2(5H)-one | 140628-64-4

• 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: 5-methyl-5-styrylfuran-2(5H)-one
• 英文别名: 5-methyl-5-[(E)-2-phenylethenyl]-2,5-dihydrofuran-2-one；5-methyl-5-[(E)-2-phenylethenyl]furan-2-one
• CAS: 140628-64-4
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: QESCCKFXSFDWHF-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 、 三氯化铁 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 20.0h， 以82%的产率得到5-methyl-5-styrylfuran-2(5H)-one
  参考文献：
  名称：

  由三羰基（乙烯基乙烯酮）铁（0）配合物合成三羰基（乙烯基烯丙基）铁（0）配合物并将其氧化为5,5-二取代的呋喃-2（5 H）-

  摘要：

  将膦酰基乙酸根阴离子加到三羰基（乙烯基乙烯酮）铁（0）配合物中，得到三羰基（乙烯基烯丙基）铁（0）配合物中。通过观察[Fe o {PhCH CHC（Me）C CHCO 2 Bu t }（CO）3的主要异构体的X射线晶体结构分析，观察到高达98：2的立体选择性，并阐明了主要立体异构体的相对立体化学。] 9d，是由[Fe o {PhCH CHC（Me）C O}（CO）3 ] 7a与（EtO）2 P（O）CH 2 CO的阴离子反应得到的产物2卜吨8B。三羰基（乙烯基烯丙基）铁（ 0）配合物的主要异构体与FeCl 3的反应得到5，5-二取代的呋喃-2（5 H）-一。

  DOI：

  10.1039/p19920000259

文献信息

• Design, synthesis and in vitro evaluation against human cancer cells of 5-methyl-5-styryl-2,5-dihydrofuran-2-ones, a new series of goniothalamin analogues
  作者：Marjorie Bruder、Débora Barbosa Vendramini-Costa、João Ernesto de Carvalho、Ronaldo Aloise Pilli

  DOI：10.1016/j.bmc.2013.06.044

  日期：2013.9

  The present work describes the preparation of a novel series of compounds based on the structure of goniothalamin (1), a natural styryl lactone with known cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 17 goniothalamin analogues displaying the 5-methyl-2,5-dihydrofuran-2-one motif were prepared, and their cytotoxicity evaluated. While the analogues bearing methoxy and/or hydroxy groups on the aromatic moiety usually were at least three times less potent than the lead compound (1), ortho and para-trifluoromethyl analogues 10 and 11 exhibited levels of cytotoxicity similar to goniothalamin (1) against most cancer cell lines evaluated. One could suggest that the electronic effect of the trifluoromethyl group activates the inhibitor's electrophilic site via reduction of the electron density of the alpha,beta-unsaturated ester oxygen atom. These results provide new information on the structure activity relationship of these alpha,beta-unsaturated styryl lactones, thereby further focusing the design of novel candidates. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of tricarbonyl(vinylallene)iron(0) complexes from tricarbonyl(vinylketene)iron(0) complexes and their oxidation to 5,5-disubstituted furan-2(5H)-ones
  作者：Stephen P. Saberi、Susan E. Thomas

  DOI：10.1039/p19920000259

  日期：——

  Addition of phosphonoacetate anions to tricarbonyl(vinylketene)iron(0) complexes gave tricarbonyl(vinylallene)iron(0) complexes. Stereoselectivity as high as 98 : 2 was observed and the relative stereochemistry of the major stereoisomers was elucidated by X-ray crystal structure analysis of the major isomer of [FeoPhCHCHC(Me)CCHCO2But}(CO)3]9d, the product obtained from the reaction between [Feo

  将膦酰基乙酸根阴离子加到三羰基（乙烯基乙烯酮）铁（0）配合物中，得到三羰基（乙烯基烯丙基）铁（0）配合物中。通过观察[Fe o PhCH CHC（Me）C CHCO 2 Bu t }（CO）3的主要异构体的X射线晶体结构分析，观察到高达98：2的立体选择性，并阐明了主要立体异构体的相对立体化学。] 9d，是由[Fe o PhCH CHC（Me）C O}（CO）3 ] 7a与（EtO）2 P（O）CH 2 CO的阴离子反应得到的产物2卜吨8B。三羰基（乙烯基烯丙基）铁（ 0）配合物的主要异构体与FeCl 3的反应得到5，5-二取代的呋喃-2（5 H）-一。