Ethyl 4-bromo-3-thiophen-2-ylbut-2-enoate | 170145-87-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl 4-bromo-3-thiophen-2-ylbut-2-enoate
• CAS: 170145-87-6
• 化学式: C₁₀H₁₁BrO₂S
• 分子量: 275.166
• InChiKey: IUAQXXXKZRKNTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-乙酰基-1H-吡咯-2-甲醛 、 Ethyl 4-bromo-3-thiophen-2-ylbut-2-enoate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以42%的产率得到ethyl 2-acetyl-6-(thiophen-2-yl)indolizine-7-carboxylate
  参考文献：
  名称：

  The synthesis, characterization and optical properties of novel 2-acyl 6-arylindolizines

  摘要：

  A series of novel 2-acyl-6-aryl substituted indolizine derivatives was synthesized by a novel tandem reaction between 4-acyl-pyrrole-2-carbaldehyde derivatives and ethyl 4-bromo-3-arylbut-2-enoate under mild conditions. The compounds were characterized using IR, H-1 NMR C-13 NMR and HRMS. The crystal structure of 7a was determined using single crystal X-ray crystallography. The absorption results showed that compounds 7a-e presented their absorption maxima at ca. 270 nm, while compounds 7f and 7g with a larger conjugation system exhibited red-shifted absorption character (ca. 280 nm). Fluorescence spectra revealed that these compounds exhibited blue fluorescence (434-456 nm) in dilute solutions and showed quantum yields of fluorescence between 0.02 and 0.39 in dichloromethane. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.06.146
• 作为产物：
  描述：

  3-(2-Thienyl)crotonsaeureaethylester 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 10.0h， 生成 Ethyl 4-bromo-3-thiophen-2-ylbut-2-enoate
  参考文献：
  名称：

  Rh催化的γ-邻苯二甲酰亚胺取代的α,β-不饱和羧酸酯的不对称氢化：β-芳基-γ-氨基酸的高效对映选择性合成

  摘要：

  DOI：

  10.1021/ol801179x

文献信息

• Rh-Catalyzed Asymmetric Hydrogenation of γ-Phthalimido-Substituted α,β-Unsaturated Carboxylic Acid Esters: An Efficient Enantioselective Synthesis of β-Aryl-γ-amino Acids
  作者：Jun Deng、Zheng-Chao Duan、Jia-Di Huang、Xiang-Ping Hu、Dao-Yong Wang、Sai-Bo Yu、Xue-Feng Xu、Zhuo Zheng

  DOI：10.1021/ol801179x

  日期：2008.8.7
• The synthesis, characterization and optical properties of novel 2-acyl 6-arylindolizines
  作者：Yan Qing Ge、Xue Yong Gong、Guang Jie Song、Xiao Qun Cao、Jian Wu Wang

  DOI：10.1016/j.saa.2014.06.146

  日期：2015.1

  A series of novel 2-acyl-6-aryl substituted indolizine derivatives was synthesized by a novel tandem reaction between 4-acyl-pyrrole-2-carbaldehyde derivatives and ethyl 4-bromo-3-arylbut-2-enoate under mild conditions. The compounds were characterized using IR, H-1 NMR C-13 NMR and HRMS. The crystal structure of 7a was determined using single crystal X-ray crystallography. The absorption results showed that compounds 7a-e presented their absorption maxima at ca. 270 nm, while compounds 7f and 7g with a larger conjugation system exhibited red-shifted absorption character (ca. 280 nm). Fluorescence spectra revealed that these compounds exhibited blue fluorescence (434-456 nm) in dilute solutions and showed quantum yields of fluorescence between 0.02 and 0.39 in dichloromethane. (C) 2014 Elsevier B.V. All rights reserved.