5(Z)-3-benzyl-5-(2-hydroxybenzylidene)furan-2(5H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5(Z)-3-benzyl-5-(2-hydroxybenzylidene)furan-2(5H)-one
• 英文别名: (5Z)-3-benzyl-5-[(2-hydroxyphenyl)methylidene]furan-2-one
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: ACCNNWSXIFRIJA-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-((tert-butyldimethylsilyl)oxy)benzaldehyde 在 氢氟酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.0h， 生成 5(Z)-3-benzyl-5-(2-hydroxybenzylidene)furan-2(5H)-one
  参考文献：
  名称：

  Synthesis and Cytotoxic Activity of Some 3-Benzyl-5-Arylidenefuran-2(5H)-ones

  摘要：

  3-苄基-呋喃-2(5H)-酮（2a）和3-(4-溴苄基)-呋喃-2(5H)-酮（2b）与TBDMSOTf反应，转化为相应的叔丁基二甲基硅基呋喃醚。这些呋喃进一步与几种芳香醛缩合，获得了通用的3-苄基-5-芳亚基-呋喃-2(5H)-酮结构的化合物5-14，产率为31%至98%。这些化合物是天然产生的诺斯特克乳酸酯的类似物，已被报道具有中等的细胞毒活性。化合物5-14被提交进行体外生物测定，针对HL-60、HCT-8、SF295和MDA-MB-435癌细胞系，使用MTT细胞毒性测定法。

  DOI：

  10.3390/12051101

文献信息

• Synthesis of Photosynthesis-Inhibiting Nostoclide Analogues
  作者：Róbson R. Teixeira、Luiz C. A. Barbosa、Giuseppe Forlani、Dorila Piló-Veloso、José Walkimar de Mesquita Carneiro

  DOI：10.1021/jf072964g

  日期：2008.4.1

  A series of 34 3-benzyl-5-(arylmethylene)furan-2(5H)-ones, designed using the naturally occurring toxins nostoclides as a lead structure, was synthesized as potential inhibitors of the photosynthetic electron transport. All compounds were fully characterized by IR, NMR (H-1 and C-13), and MS spectrometry. HMBC and HSQC bidimensional experiments allowed 13 C and H-1 assignments. Their biological activities were evaluated in vitro as the ability to interfere with light-driven reduction of ferricyanide by isolated spinach chloroplasts. About two-thirds of the compounds exhibited inhibitory properties in the micromolar range against the basal electron flow from water to K-3[Fe(CN)(6)]. The inhibitory potential of these 3-benzyl-5-(aryl methylene)furan-2(5H)-one lactones is higher than that of other nostoclide analogues previously synthesized in the same laboratories.
• Synthesis, structural characterization and conformational aspects of nostoclide analogues
  作者：R.R. Teixeira、L.C.A. Barbosa、J.W.de M. Carneiro、R.S. Corrêa、J. Ellena、A.C. Doriguetto

  DOI：10.1016/j.molstruc.2008.06.019

  日期：2009.1

  The synthesis and structural analysis of a set of nostoclide analogues with potential herbicide activity is described. The influence of intra- and intermolecular hydrogen bonding, as well as other interactions on the conformation and packing of the compounds is thoroughly described using DFT calculations and single crystal X-ray diffraction analyses. All lactones exhibited the Z configuration as confirmed by NOESY experiments and by single crystal X-ray diffraction measurements. (c) 2008 Elsevier B.V. All rights reserved.