2,2'-[(4-Bromophenyl)methylene]bis(3,5-dimethyl-1H-pyrrole) | 850454-08-9

• 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: 2,2'-[(4-Bromophenyl)methylene]bis(3,5-dimethyl-1H-pyrrole)
• 英文别名: 2-[(4-bromophenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)methyl]-3,5-dimethyl-1H-pyrrole
• CAS: 850454-08-9
• 化学式: C₁₉H₂₁BrN₂
• 分子量: 357.293
• InChiKey: CLXAVVXGMNMIAG-UHFFFAOYSA-N

物化性质

• 沸点：
  502.3±45.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,2'-[(4-Bromophenyl)methylene]bis(3,5-dimethyl-1H-pyrrole) 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四氯苯醌 、 potassium carbonate 、 三乙胺 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 25.5h， 生成 C₃₇H₃₈BF₂N₃
  参考文献：
  名称：

  通过分子设计调节Bodipy-咔唑供体-受体二元组的吸收和电荷转移†

  摘要：

  三个基于BODIPY-（BDP = 4,4-二氟-4-硼-3a，4a-二氮杂-小号-indacene）供体-受体成对设计并合成，和它们的基态和光物理性质进行了系统的表征。的BDP发色团和给电子基咔唑（CARB）部分之间的电子耦合被连接调谐经由所述内消旋和测试上的BDP核心的位置，并且通过使用各种化学接头（苯基和炔基）的，得到的内消旋BDP -Carb，中观BDP- phen- Carb和beta BDP- alk- Carb。中观发现取代的二元组保留了未取代的BDP的基态吸收特征。但是，通过控制光致内部电荷转移（ICT）的速率，供体和受体部分之间的键合关系的变化调节了激发态失活的光物理行为。所述的β -取代的二分体显着调谐（红移）的吸收光谱，在保留BDP的期望的特性，尤其是稳定性和高消光系数，然而ICT动力学进行了比较，加速内消旋取代的成对层。密度泛函理论（DFT）和时间依赖DFT（TDD

  DOI：

  10.1039/c9dt00094a
• 作为产物：
  描述：

  2,4-二甲基吡咯 、 对溴苯甲醛 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,2'-[(4-Bromophenyl)methylene]bis(3,5-dimethyl-1H-pyrrole)
  参考文献：
  名称：

  在 BODIPY 衍生物存在下通过胺与 2-氨基苯硫酚的光催化氧化缩合合成 2-芳基苯并噻唑

  摘要：

  摘要 开发了一种简单、方便、高效的非金属催化剂在温和条件下合成2-芳基苯并噻唑的新方法。硼-二吡咯甲烯 (BODIPY) 染料用作光催化剂，用于胺与 2-氨基苯硫酚的有氧氧化反应。该方法对于苯并噻唑衍生物的合成和光催化反应的发展非常有用。图形概要

  DOI：

  10.1080/00397911.2014.932811

文献信息

• Syntheses of 2-Aryl Benzothiazoles via Photocatalyzed Oxidative Condensation of Amines with 2-Aminothiophenol in the Presence of BODIPY Derivatives
  作者：Zeyin Zhou、Weijun Yang

  DOI：10.1080/00397911.2014.932811

  日期：2014.11.2

  Abstract A simple, convenient, and efficient new method for synthesis of 2-aryl benzothiazoles under mild conditions with nonmetal catalyst has been developed. Boron–dipyrromethene (BODIPY) dyes were used as photocatalysts for aerobic oxidative reactions of amine with 2-aminothiophenol. The approach will be very useful for the synthesis of benzothiazole derivatives and the development of photocatalytic

  摘要 开发了一种简单、方便、高效的非金属催化剂在温和条件下合成2-芳基苯并噻唑的新方法。硼-二吡咯甲烯 (BODIPY) 染料用作光催化剂，用于胺与 2-氨基苯硫酚的有氧氧化反应。该方法对于苯并噻唑衍生物的合成和光催化反应的发展非常有用。图形概要
• A bodipy based dual functional probe for the detection of hydrogen sulfide and H₂S induced apoptosis in cellular systems
  作者：Neha Gupta、Shahi Imam Reja、Vandana Bhalla、Muskan Gupta、Gurcharan Kaur、Manoj Kumar

  DOI：10.1039/c5cc02984h

  日期：——

  A bodipy based dual functional probe1has been designed and synthesized, which selectively detects H₂S as well as monitors H₂S induced apoptosis in cells.

  一种基于bodipy的双重功能探针1已被设计和合成，可选择性地检测H2S，并监测H2S诱导的细胞凋亡。
• Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs
  作者：Jaime H. Gibbs、Larry T. Robins、Zehua Zhou、Petia Bobadova-Parvanova、Michael Cottam、Gregory T. McCandless、Frank R. Fronczek、M. Graça H. Vicente

  DOI：10.1016/j.bmc.2013.07.017

  日期：2013.9

  A series of twenty-two BODIPY compounds were synthesized, containing various meso-phenyl and meso-thienyl groups, and their spectroscopic and structural properties were investigated using both experimental and computational methods. Further functionalization of the BODIPY framework via iodination at the 2,6-pyrrolic positions was explored in order to determine the effect of these heavy atoms on the photophysical and cytotoxicity of the meso-aryl-BODIPYs. BODIPYs bearing meso-thienyl substituents showed the largest red-shifted absorptions and emissions and reduced fluorescence quantum yields. The phototoxicity of the BODIPYs in human carcinoma HEp2 cells depends on both the presence of iodines and the nature of the meso-aryl groups. Six of the eleven 2,6-diiodo-BODIPYs investigated showed at least a sevenfold enhancement in phototoxicity (IC50 = 3.5-28 mu M at 1.5 J/cm(2)) compared with the non-iodinated BODIPYs, while the others showed no cytotoxicity, while their singlet oxygen quantum yields ranged from 0.02 to 0.76. Among the series investigated, BODIPYs 2a and 4a bearing electron-donating meso-dimethoxyphenyl substituents showed the highest phototoxicity and dark/phototoxicity ratio, and are therefore the most promising for application in PDT. (C) 2013 Elsevier Ltd. All rights reserved.
• Convenient one-pot procedure for synthesizing 4,4′-dimethoxy-boradiaza-s-indacene dyes and their application to cell labeling
  作者：Kuan-Miao Liu、Ming-Shan Tsai、Ming-Shiou Jan、Chi-Min Chau、Wan-Ju Wang

  DOI：10.1016/j.tet.2011.08.043

  日期：2011.10

  We succeeded in developing a convenient one-pot pathway for synthesizing 4,4'-dimethoxy-boradiaza-s-indacene dyes 4a-d. The structures feature two methoxy groups in place of the fluorine atoms in 4,4'-difluoro-4-boradiaza-s-indacene. These novel dyes emitted green fluorescence and possessed moderate to high fluorescence quantum yields (Phi=0.32-0.93). We demonstrated that these dyes have applicability to cell labeling. (C) 2011 Elsevier Ltd. All rights reserved.
• Design, synthesis and characterization of a novel fluorescent probe for nitric oxide based on difluoroboradiaza-s-indacene fluorophore
  作者：Xian Zhang、Hua-shan Zhang

  DOI：10.1016/j.saa.2004.05.041

  日期：2005.4

  Nitric oxide (NO) is a gaseous. free radical, which plays a role as an intracellular second messenger and a diffusible intercellular messenger. To obtain evidence for NO function in vivo, 1,3,5,7-tetramethyl-8-(4'-aminophenyl-N-(2"-amino)-phenzyl)-difluoroboradiaza-s-indacene (TMAPABODIPY) was designed and synthesized as a fluorescent probe for nitric oxide, which features high photostability and no pH dependency over a wide pH range. The fluorescence of TMAPABODIPY itself is very strong. When TMAPABODIPY traps NO in the presence of dioxygen, the weak fluorescent triazole form is obtained, which offers the advantages of specificity, and sensitivity for direct detection of NO. The relationship was obtained between the quenching fluorescence intensity and NO concentration in the range 0.02-4.0 mu mol l(-1). The detection limit is 5 nmol l(-1) (S/N = 3). The proposed method has been used to monitor the release of NO from S-nitrosocysteine, a NO-releasing agent. (c) 2004 Elsevier B.V. All rights reserved.