(5Z)-3-benzyl-5-(3-methylbenzylidene)furan-2(5H)-one | 1019842-75-1

• 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: (5Z)-3-benzyl-5-(3-methylbenzylidene)furan-2(5H)-one
• 英文别名: (5Z)-3-benzyl-5-[(3-methylphenyl)methylidene]furan-2-one
• CAS: 1019842-75-1
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: CSIBBPMVGUYTBC-PDGQHHTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以156 mg的产率得到(5Z)-3-benzyl-5-(3-methylbenzylidene)furan-2(5H)-one
  参考文献：
  名称：

  Synthesis, structural characterization and conformational aspects of nostoclide analogues

  摘要：

  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.

  DOI：

  10.1016/j.molstruc.2008.06.019

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.