ethyl 4-methyl-3-trifluoromethyl-2-pyrrolecarboxylate | 127074-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 4-methyl-3-trifluoromethyl-2-pyrrolecarboxylate
• 英文别名: ethyl 3-(trifluoromethyl)-4-methylpyrrole-2-carboxylate；Ethyl 4-methyl-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate
• CAS: 127074-06-0
• 化学式: C₉H₁₀F₃NO₂
• 分子量: 221.179
• InChiKey: LWMRUFRJVPJQFU-UHFFFAOYSA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  287.2±40.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-methyl-3-trifluoromethyl-2-pyrrolecarboxylate 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 4,4-difluoro-1,2,3,5,6,7-hexamethyl-8-(4-dimethylaminophenyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Synthesis, crystal structures and spectroscopic characterizations of two difluoroboradiaza-s-indacene dyes

  摘要：

  Two new 8-(4-dimethylaminophenyl) substituted boron-dipyrromethene (BDP) dyes: 1,2,6,7-tetraethyl-4,4-difluoro-3,5-dimethyl8-(4-dimethylaminophenyl)-4-bora-3a,4a-diaza-s-indacene (5) and 4,4-difluoro-1,2,3,5,6,7-hexamethyl-8-(4-dimethylaminophenyl)4-bora-3a,4a-diaza-s-indacene (6) have been synthesized and their crystal structures are determined by X-ray diffraction analysis. The torsion angles of 8-phenyl ring and the indacene plane are 79.61 degrees for 5 and 87.56 degrees for 6, respectively. The absorption and steady-state fluorescence properties in different solvents have been investigated. The fluorescence quantum yields of the two dyes are lower in more polar solvents, which can be ascribed to the intramolecular charge transfer from the aniline to the BDP unit. Protonation of the aniline moiety at low pH in MeOH-H2O (1:1 v/v) solution causes a large fluorescence enhancement. The pk(a) values calculated from the pH dependent fluorescence emission spectra are 3.14 for 5 and 3.09 for 6, respectively. They are suitable as pH probes excitable with visible light. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2006.05.014
• 作为产物：
  描述：

  氰乙酸乙酯 、 2-acetoxy-3-nitro-1,1,1-trifluorobutane 以60%的产率得到
  参考文献：
  名称：

  ONO, NOBORU;KAWAMURA, HISAYUKI;MARUYAMA, KAZUHIRO, BULL. CHEM. SOC. JAP., 62,(1989) N0, C. 3386-3388

  摘要：

  DOI：

文献信息

• A Convenient Synthesis of Trifluoromethylated Pyrroles and Porphyrins
  作者：Noboru Ono、Hisayuki Kawamura、Kazuhiro Maruyama

  DOI：10.1246/bcsj.62.3386

  日期：1989.10

  4-Alkyl-3-trifluoromethyl-2-pyrrolecarboxylic acid esters (2) were conveniently prepared by the reaction of trifluoromethylated β-nitro acetates (1) with ethyl isocyanoacetate. The pyrroles were converted into the corresponding porphyrins via tetramerization of 2-(hydroxymethyl)pyrroles.

  4-烷基-3-三氟甲基-2-吡咯甲酸酯（2）可通过三氟甲基化β-硝基乙酸酯（1）与异氰乙酸乙酯反应方便地制备。吡咯通过 2-（羟甲基）吡咯的四聚作用转化为相应的卟啉。