5-(2-hydroxyphenyl)dipyrromethane

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(2-hydroxyphenyl)dipyrromethane
• 英文别名: meso-(2-hydroxyphenyl)dipyrromethane；meso-(2-hydroxyphenylene)-2,2'-dipyrrolylmethane；2-hydroxyphenyldipyrromethane；2-(di(1H-pyrrol-2-yl)methyl)phenol；meso-(o-hydroxyphenyl)dipyrromethane；2-[bis(1H-pyrrol-2-yl)methyl]phenol
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: BWHPSGWGIIZVPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(2-hydroxyphenyl)dipyrromethane 在 氢溴酸 、 苯酚 作用下， 以 乙醇 为溶剂， 反应 2.05h， 生成 ruthenium(II) 10-(2-hydroxyphenylene)-2.18-diethyl-3,17-dimethylporphyrinate (CO)(H2O)
  参考文献：
  名称：

  Complexation of zinc(II) and ruthenium(II) porphyrinates with methyl glycinate and methyl m-aminobenzoate

  摘要：

  Zinc(II) and ruthenium(II) monohydroxyporphyrinates with a different arrangement of the reaction center in the meso-aryl moiety of the macrocycle were synthesized, and their ability of complexing with the methyl esters of glycine and m-aminobenzoic acid in toluene were studied using the methods of spectrophotometric titration and H-1 NMR spectroscopy. The stability constants of the resulting complexes and concentration ranges of their existence were determined.

  DOI：

  10.1134/s1070363213050204
• 作为产物：
  描述：

  吡咯 、 水杨醛 在 silica-supported sulfuric acid 作用下， 反应 0.03h， 以54%的产率得到5-(2-hydroxyphenyl)dipyrromethane
  参考文献：
  名称：

  无溶剂条件下H2SO4·SiO2催化快速环保合成二吡咯甲烷

  摘要：

  在室温下，西里卡负载的硫酸首次被用作非均相，可重复使用和高效的催化剂，从而在很短的反应时间内生成相应的二吡咯甲烷。新的反应过程很简单，不需要溶剂。

  DOI：

  10.1002/cjoc.201090063

文献信息

• Thiourea dioxide promoted efficient organocatalytic one-pot synthesis of a library of novel heterocyclic compounds
  作者：Sanny Verma、Subodh Kumar、Suman L. Jain、Bir Sain

  DOI：10.1039/c1ob05818e

  日期：——

  The utility of thiourea dioxide as an efficient organocatalyst for the library synthesis of novel heterocyclic compoundsvia one-pot multicomponent coupling reactions is disclosed. Thiourea dioxide is an inexpensive and readily accessible catalyst, resulting in better product yields as compared to the corresponding thiourea as catalyst. Thiourea dioxide is found to be insoluble in various organic solvents and therefore at the end of the reaction products can be separated by extraction with diethyl ether and the recovered catalyst can be used several times with consistent catalytic activity.

  介绍了二氧化硫脲作为高效有机催化剂在一锅多组分偶联反应中合成新型杂环化合物的应用。与相应的硫脲催化剂相比，二氧化硫脲作为一种廉价且易于获得的催化剂，能带来更好的产物收率。二氧化硫脲在多种有机溶剂中难以溶解，因此反应结束后，产物可通过乙醚萃取分离，且回收的催化剂能多次重复使用，保持稳定的催化活性。
• Synthesis of BF₂ Complexes of Prodigiosin Type Oligopyrroles
  作者：M. Rajeswara Rao、Manu D. Tiwari、Jayesh R. Bellare、M. Ravikanth

  DOI：10.1021/jo201183s

  日期：2011.9.2

  We developed a simple, facile route for the synthesis of BF2 complexes of prodigiosin type oligopyrroles and their cholesterol conjugates. This route gives an access to synthesize any desired meso-aryl-substituted 3-pyrrolyl BODIPYs which were not easily accessible earlier.

  我们开发了简单，简便的路线来合成prodigiosin型oligopyrroles及其胆固醇共轭物的BF 2复合物。该路线提供了合成任何所需的内消旋-芳基取代的3-吡咯基BODIPY的途径，这是较不容易获得的。
• Rationally Designed Fluorescent pH Sensors for Measurements in Extremely Alkaline Media
  作者：Nurcan Tuncer、Efdal Teknikel、Canan Unaleroglu

  DOI：10.1007/s10895-018-2310-8

  日期：2018.11

  meso-phenol BODIPY to achieve fluorescent pH sensors working in extreme alkalinity. We demonstrated the effects of substituents on meso, α, γ and position of the hydroxyl group on pKa. By considering these parameters, we developed pH sensors working above 11.0 in aqueous medium (ethanol/water 1:1). One of these sensors had a pKa of 12.0 and enabled the measurement of pH up to 13.6. This highly photostable

  我们研究了pK对内苯酚BODIPY的增加影响，以实现在极端碱度下工作的荧光pH传感器。我们证明了取代基对内消旋，α，γ和pK a上羟基位置的影响。通过考虑这些参数，我们开发了在水性介质（乙醇/水1：1）中工作于11.0以上的pH传感器。这些传感器之一的pK a为12.0，可测量高达13.6的pH。这种高度光稳定和明亮的传感器化合物可以轻松地由廉价的起始原料合成。
• Physicochemical and computational insight of ¹⁹F NMR and emission properties of <i>meso</i>-(<i>o</i>-aryl)-BODIPYs
  作者：Mónica Farfán-Paredes、Oscar González-Antonio、Diana E. Tahuilan-Anguiano、Jorge Peón、Armando Ariza、Pascal G. Lacroix、Rosa Santillan、Norberto Farfán

  DOI：10.1039/d0nj02576c

  日期：——

  series of electronic and physicochemical parameters were explored to determine their effect on experimental spectroscopic and photophysical data. Through a systematic obtention of a series of meso-(o-aryl)-BODIPYs, 19F NMR spectra were analyzed and their fluorescence quantum yields in several solvents were measured. Experimental values of 19F chemical shift difference ΔδF correlate well with σ-Hammett constants

  探索了一系列电子和理化参数，以确定它们对实验光谱和光物理数据的影响。通过系统地获得一系列内消旋-（o-芳基）-BODIPY，分析了19 F NMR光谱，并测量了它们在几种溶剂中的荧光量子产率。的实验值19 ˚F化学位移差Δ δ ˚F与σ-Hammett常数很好地相关，后者表示氟原子上官能团的感应性质。通过对旋转能垒，静电势图，组电负性，电荷分配和硬度/柔软度的计算DFT探索，可以深入了解这些特征如何与测量的特征直接相关。对这些特性的扩展理解提供了设计论据和结构-性质关系，这将以更有利的方式帮助理解合成分子的特性以及与结构相关的未来尝试。
• Lysosome targeting fluorescence probe for imaging intracellular thiols
  作者：Dnyaneshwar Kand、Tanmoy Saha、Mayurika Lahiri、Pinaki Talukdar

  DOI：10.1039/c5ob00889a

  日期：——

  A BODIPY-based fluorescence turn-on probe for lysosomal localization and biothiol sensing is reported.

  报道了一种基于BODIPY的荧光开启探针，用于溶酶体定位和生物硫醇检测。