2-formyl-4-iodo-3,5-dimethylpyrrole | 100517-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-formyl-4-iodo-3,5-dimethylpyrrole
• 英文别名: 4-iodo-3,5-dimethyl-1H-pyrrole-2-carbaldehyde
• CAS: 100517-15-5
• 化学式: C₇H₈INO
• 分子量: 249.051
• InChiKey: KXGVEMFJMYVQHB-UHFFFAOYSA-N

物化性质

• 熔点：
  167-170 °C(Solv: methanol (67-56-1))
• 沸点：
  318.5±42.0 °C(Predicted)
• 密度：
  1.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-formyl-4-iodo-3,5-dimethylpyrrole 在 三氟化硼乙醚 、 三氯氧磷 作用下， 以 二氯甲烷 、 正戊烷 为溶剂， 反应 2.25h， 生成 2-iodo-1,3,5,7-tetramethyl-4,4-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  一锅TMS裂解点击反应荧光标记磷酸胆碱脂质的烷基链

  摘要：

  基于易于制备的TMS-炔烃-BODIPY标记试剂（1），描述了一种简单的点击策略，用于荧光标记磷胆碱脂质的含叠氮基烷基链。脂质标记是通过一锅Ag（I）催化的1脱保护，然后在温和的水醇条件下以高收率在原位Cu（I）介导的炔烃染料与叠氮化物-磷脂对应物的环加成反应来进行的。由于该反应与磷酸胆碱的首基相容，因此在此以合成正十六烷基磷酸胆碱的荧光类似物（利什曼杀菌剂（miltefosine））为例。此外，制备了一种新型的强荧光2-酰基BODIPY染料（6）据报道，空前的一锅Ag（I）催化TMS裂解/炔烃水合1；该化合物也可以是含氨基生物分子的方便标记试剂。

  DOI：

  10.1016/j.jphotochem.2012.06.005
• 作为产物：
  描述：

  3,5-二甲基-2-吡咯甲醛 在 碘 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以85%的产率得到2-formyl-4-iodo-3,5-dimethylpyrrole
  参考文献：
  名称：

  蒽-BODIPY盒：合成和能量转移。

  摘要：

  基于4,4-二氟-1,3,5,7-四甲基-4-硼3a，4a-二氮杂-s-茚满二烯（BODIPY）骨架的化合物是出色的荧光标记。当这种BODIPY染料与在相对短的波长吸收的官能团缀合时，这些官能团可以在某些分子中将吸收的能量传输到BODIPY，然后发出荧光。在这种情况下，BODIPY片段充当受体，而另一组充当供体。这种供体-受体盒系统中的能量转移效率必须随两个组件的相对方向以及与连接它们的连接体的结构而变化。本研究旨在针对供体和受体片段之间的连接子缀合的特殊情况探讨这些问题。为此，准备了暗盒3-10。进行了电化学研究，以了解这些系统中供体-受体结合的程度。对化合物7和9的单晶进行的X射线晶体学研究表明，固态供体和受体片段的结构良好。记录化合物的吸收，荧光和时间分辨荧光光谱，并测量供体λ（max）激发的盒的量子产率。确定暗盒3和9的荧光稳态各向异性数据，以提供有关跃迁偶极矩相互方向的信息。对化

  DOI：

  10.1002/chem.200304754

文献信息

• A New «off-on» Fluorescence Zinc Ion Sensors Based on Iodo- and Bromosubstituted Dipyrromethenes
  作者：Ekaterina N. Nuraneeva、Galina B. Guseva、Elena V. Antina

  DOI：10.1007/s10895-020-02670-4

  日期：2021.3

  the binary propanol-1/cyclohexane mixture (1:30). The fluorometric detection limit of Zn2+ ions using HL1 – HL3 sensors is from 3.0∙10−8 to 3.3·10−9 mol/L. The presence of Na+, K+, Ca2+, Mg2+, Mn2+, Ni2+, Co2+, Pb2+ cations does not interfere with the detection of Zn2+. Complexation reactions are accompanied by a visual change in the color of the solution from yellow-orange to pink-raspberry so that the

  基于螯合增强荧光（CHEF）的作用，单碘和二溴取代的二吡咯烷酮HL 1 -HL 3被描述为对Zn 2+具有高度敏感性和选择性的“关闭”荧光化学传感器。HL 1 – HL 3与Zn 2+阳离子的配位反应伴随着在二元丙醇-1 /环己烷混合物（1:30）中其他金属离子的背景下荧光强度显着增加（124至215倍） 。使用HL 1 – HL 3传感器对Zn 2+离子的荧光检测极限为3.0∙10 -8至3.3·10 -9 摩尔/升。Na +，K +，Ca 2 +，Mg 2 +，Mn 2 +，Ni 2 +，Co 2 +，Pb 2+阳离子的存在不会干扰Zn 2+的检测。络合反应伴随着溶液颜色从黄橙色到粉红色覆盆子的视觉变化，因此HL 1 -HL 3配体也可以用作Zn 2+存在的“裸眼”指示剂离子。
• Asymmetric Dipyrrin and <i>F</i>-BODIPYs Conjugated to Terminal Alkynes and Alkenes
  作者：Carlotta Figliola、Katherine N. Robertson、Sarah Greening、Alison Thompson

  DOI：10.1021/acs.joc.7b01129

  日期：2017.7.7

  meso-H dipyrrin featuring a conjugated terminal alkyne substituent was converted to its corresponding difluoro boron complex, and the extent of π-conjugation was extended using Sonogashira cross-coupling. Treatment of the alkyne-substituted dipyrrin with BF3·OEt2 and NEt3 revealed the reactivity of the conjugated terminal alkyne toward Lewis-activated electrophilic substitution and led to the isolation

  具有共轭末端炔取代基的不对称中氢二吡啶被转化为其相应的二氟硼配合物，并使用Sonogashira交叉偶联扩展了π共轭的程度。用BF 3 ·OEt 2和NEt 3处理炔烃取代的双吡啶具有共轭末端炔烃对路易斯活化的亲电取代基的反应性，并导致带有末端溴乙烯和烯醇取代基的F -BODIPY的分离。
• Fluorogenic α-Tocopherol Analogue for Monitoring the Antioxidant Status within the Inner Mitochondrial Membrane of Live Cells
  作者：Katerina Krumova、Lana E. Greene、Gonzalo Cosa

  DOI：10.1021/ja408227f

  日期：2013.11.13

  We report here the preparation of a lipophilic fluorogenic antioxidant (Mito-Boclipy-TOH) that targets the inner mitochondrial lipid membrane (IMM) and is sensitive to the presence of lipid peroxyl radicals, effective chain carriers in the lipid chain autoxidation. Mito-Bodipy-TOH enables monitoring of the antioxidant status, i.e., the antioxidant load and ability to prevent lipid chain autoxidation, within the inner mitochondrial membrane of live cells. The new probe consists of 3 segments: a receptor, a reporter, and a mitochondria-targeting element, constructed, respectively, from an alpha-tocopherol-like chromanol moiety, a BODIPY fluorophore, and a triphenylphosphonium cation (TPP). The chromanol moiety ensures reactivity akin to that of a-tocopherol, the most potent naturally occurring lipid soluble antioxidant, while the BODIPY fluorophore and TPP ensure partitioning within the inner mitochondrial membrane. Mechanistic studies conducted either in homogeneous solution or in liposomes and in the presence of free radical initiators show that the antioxidant activity of Mito-Bodipy-TOH is on par with that of a-tocopherol. Studies conducted on live fibroblast cells further show the antioxidant depletion in the presence of methyl viologen (paraquat), a known agent of oxidative stress and source of superoxide radical anion (and indirectly, a causative of lipid peroxidation) within the mitochondria matrix. We recorded a ca. 8-fold emission enhancement with Mito-Bodipy-TOH in cells stressed with methyl viologen, whereas no enhancement was observed in control studies with untreated cells. Our findings underscore the potential of the new fluorogenic antioxidant Mito-Bodipy-TOH to study the chemical link between antioxidant load, lipid peroxidation and mitochondrial physiology.
• Synthesis and spectral properties of new 3,3’-bis(dipyrrolylmethene) with acetylene spacer
  作者：E. V. Antina、G. B. Guseva、A. E. Loginova、A. S. Semeikin、A. I. V’yugin

  DOI：10.1134/s107036321011023x

  日期：2010.11

  Bis(2,4,7,9-tetramethyl-8-ethyldipyrrolylmethen-3-yl)acetylene dihydrobromide (H2L center dot 2HBr), new bis(dipyrrolylmethene), in whose molecule dipyrrolylmethene domains were connected through 3,3'-carbon atoms of internal pyrrole nuclei by acetylene spacer, were synthesized by original procedure. The compound was characterized by element analysis, IR, H-1 NMR, and electronic spectroscopy. The comparative analysis of spectral properties shows the reduction of the basicity of H2L ligand in comparison with the structural analogs, which contain internal methylene spacer. The quantum-chemical simulation showed that the rigid acetylene spacer gives linear structure to the H2L molecule in contrast to the spiral-shaped geometry of structural analogs with -CH2- spacer.
• Preparation, spectral and thermal properties of Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) complexes with iodosubstituted 2,2′-dipyrrolylmethene
  作者：G. B. Guseva、E. V. Antina、M. B. Beresin、A. I. V’yugin、E. N. Nuraneeva

  DOI：10.1134/s1070363213080161

  日期：2013.8

  Complexes [ML2] of cobalt(II), nickel(II), copper(II), zinc(II), and cadmium(II) with asymmetrically substituted (E)-3-ethyl-5-[(4-iodo-3,5-dimethyl-2H-pyrrol-2-ylidene)methyl]-2,4-dimethyl-1H-pyrrole (HL) have been prepared and characterized for the first time. The spectral properties, stability in solutions and in the solid phase at elevated temperature of the complexes have been studied. The effects of complexing metal ion and the reaction medium on the spectral luminescent properties (absorptivity, quantum yield, fluorescence lifetime, and the radiation constant) and on thermal destruction of the [ML2] complexes have been discussed.