(Z)-3-benzyl-5-((5-(4-bromophenyl)furan-2-yl)methylene)furan-2(5H)-one | 1370658-09-5

• 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: (Z)-3-benzyl-5-((5-(4-bromophenyl)furan-2-yl)methylene)furan-2(5H)-one
• CAS: 1370658-09-5
• 化学式: C₂₂H₁₅BrO₃
• 分子量: 407.263
• InChiKey: KLKJXUMXEZYKTA-ZHZULCJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-(phenylmethyl)-2(5H)-furanone 、 5-(4-溴苯基)-2-呋喃甲醛 在 N,N-二异丙基乙胺 、 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 2.0h， 以38%的产率得到
  参考文献：
  名称：

  Acid-Catalyzed Z-E Isomerization of γ-Alkylidenebutenolides: An Experimental and DFT Study

  摘要：

  The Z-E isomerization of.-alkylidenebutenolide analogues to natural nostoclides and other natural butenolides was investigated using H-1 nuclear magnetic resonance (NMR) and high performance liquid chromatography ( HPLC) data as well as density functional theory (DFT) calculations at the omega B97x-D/6-31G(d,p) level, including solvent effects with the polarizable continuum solvation approach. The experimental data supported the Z to E isomerization of gamma-alkylidenebutenolides under acid catalysis. Newly prepared samples have predominantly Z configuration, which partially isomerizes to the E isomer under acidic conditions. Density functional theory studies corroborate the experimental findings. While neutral gamma-alkylidenebutenolides are more stable in the Z form, protonation of the.-lactone carbonyl group results in preferential stabilization of the E isomer.

  DOI：

  10.21577/0103-5053.20190131

文献信息

• Barbosa, Luiz C. A.; Varejao, Jodieh O. S.; Petrollino, Davide, ARKIVOC, 2012, vol. 2012, # 4, p. 15 - 32
  作者：Barbosa, Luiz C. A.、Varejao, Jodieh O. S.、Petrollino, Davide、Pinheiro, Patricia F.、Demuner, Antonio J.、Maltha, Celia R. A.、Forlani, Giuseppe

  DOI：——

  日期：——