10-(4-carboxyphenyl)-5,5-bis(3-(2-methoxyethoxy)prop-1-yn-1-yl)-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide | 1232501-49-3

• 英文名称: 10-(4-carboxyphenyl)-5,5-bis(3-(2-methoxyethoxy)prop-1-yn-1-yl)-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide
• 英文别名: 7-diethylaminocoumarine-3-carboxylic acid；4-[2,2-Bis[3-(2-methoxyethoxy)prop-1-ynyl]-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl]benzoic acid
• CAS: 1232501-49-3
• 化学式: C₃₂H₃₇BN₂O₆
• 分子量: 556.467
• InChiKey: DNTWOJNTPXUPCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  10-(4-carboxyphenyl)-5,5-bis(3-(2-methoxyethoxy)prop-1-yn-1-yl)-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide 在 氯甲酸乙酯 、 三乙胺 、 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 [4-[2,2-Bis[3-(2-methoxyethoxy)prop-1-ynyl]-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl]phenyl]methanol
  参考文献：
  名称：

  [EN] DETECTION OF NEURODEGENERATIVE DISEASES
  [FR] DÉPISTAGE DE MALADIES NEURODÉGÉNÉRATIVES

  摘要：

  公开号：

  WO2017153922A3
• 作为产物：
  描述：

  3-(2-methoxyethoxy)prop-1-yne 在 bis-triphenylphosphine-palladium(II) chloride 、 乙基溴化镁 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 5.0h， 生成 10-(4-carboxyphenyl)-5,5-bis(3-(2-methoxyethoxy)prop-1-yn-1-yl)-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide
  参考文献：
  名称：

  Carbonyl Derivatives of Boradiazaindacene via Catalytic CO Insertion

  摘要：

  A methodological study is presented dealing with carbopalladation reactions on BODIPY dyes bearing aryl halogen functions. Using this technique, several ester and amide groups were efficiently introduced on the dyes. These changes do not affect the optical properties of the dyes and thus allow the construction of new BODIPY-based functional dyes with carboxylic anchoring groups or peptide links.

  DOI：

  10.1021/jo300477p

文献信息

• Fluorescent boron-substituted dipyrromethenes and use thereof for diagnosis
  申请人：De Barry Jean

  公开号：US08993781B2

  公开（公告）日：2015-03-31

  The invention relates to novel fluorescent compounds derived from non-fluorinated dipyrromethene-boron, to a method for preparing same and to the use thereof for the fluorescent marking of biological molecules. The invention also relates to biological molecules marked with said fluorescent compounds, and to the use thereof in detection methods such as medical diagnosis methods. More particularly, the detection methods of the invention are particularly useful for diagnosing neurodegenerative diseases such as Alzheimer's disease.

  该发明涉及从非氟化二吡咯甲烷硼衍生的新型荧光化合物，以及制备该化合物的方法和将其用于生物分子的荧光标记。该发明还涉及用所述荧光化合物标记的生物分子，以及将其用于诊断方法如医学诊断方法。更具体地说，该发明的检测方法特别适用于诊断诸如阿尔茨海默病等神经退行性疾病。
• The first comparative study of the ability of different hydrophilic groups to water-solubilise fluorescent BODIPY dyes
  作者：Anthony Romieu、Cédrik Massif、Sandra Rihn、Gilles Ulrich、Raymond Ziessel、Pierre-Yves Renard

  DOI：10.1039/c3nj41093e

  日期：——

  A green-emitting BODIPY dye carrying a carboxylic acid at the meso-phenyl ring was derivatised with a set of eight different hydrophilic groups neutral, negatively- or positively-charged at physiological pH. The determination of both partition coefficient (log P) and fluorescence quantum yield (ΦF) for each polar BODIPY dye allows building the first water-solubility scale for such fluorescent organic materials. This valuable tool can be used to select the most suitable molecular candidate for converting a hydrophobic BODIPY scaffold into a water-soluble and brightly fluorescent dye, and for tuning its net electric charge/polarity according to the biolabelling application targeted for this specific fluorescent marker.

  在内消旋苯环上带有羧酸的发绿光的 BODIPY 染料由一组八种不同的亲水基团衍生而成，这些亲水基团在生理 pH 下呈中性、带负电或带正电。通过测定每种极性 BODIPY 染料的分配系数 (log P) 和荧光量子产率 (ΦF)，可以为此类荧光有机材料建立第一个水溶性标度。这一有价值的工具可用于选择最合适的候选分子，将疏水性 BODIPY 支架转化为水溶性且明亮的荧光染料，并根据针对该特定荧光标记的生物标记应用来调整其净电荷/极性。
• Universal Dark Quencher Based on “Clicked” Spectrally Distinct Azo Dyes
  作者：Arnaud Chevalier、Julie Hardouin、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1021/ol402972y

  日期：2013.12.6

  The first synthesis of an heterotrifunctional molecular scaffold derived from the popular DABCYL azo dye quencher has been achieved. The sequential derviatization of this trivalent azobenzene derivative with two other nonfluorescent azo dyes (Black Hole Quencher BHQ-1 and BHQ-3) and through effective reactions from the "bioconjugation chemistry" repertoire has led to an universal dark quencher (UDQ). This "clicked" poly azo dye is able to turn off an array of fluorophores covering the UV/NIR (300-750 nm) spectral range.
• Azo-Sulforhodamine Dyes: A Novel Class of Broad Spectrum Dark Quenchers
  作者：Arnaud Chevalier、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1021/ol501753b

  日期：2014.8.1

  A rapid access to a novel class of water-soluble dark quencher dyes was achieved using an azo-coupling reaction between a fluorescent primary arylamine derived from a sulforhodamine 101 scaffold and a tertiary aniline equipped with different bioconjugatable groups. The thus obtained nonfluorescent azo-sulforhodamine hybrids display a broad quenching range spanning the visible to NIR regions. This was demonstrated through the preparation and enzymatic activation of FRET-based fluorogenic substrates of urokinase.