4,4-difluoro-8-(4-iodophenyl)-4-bora-3a,4a-diaza-s-indacene | 1222084-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,4-difluoro-8-(4-iodophenyl)-4-bora-3a,4a-diaza-s-indacene
• 英文别名: meso-(4-iodophenyl) boron-dipyrromethene；5,5-Difluoro-10-(4-iodophenyl)-5H-dipyrrolo[1,2-c:2 inverted exclamation mark,1 inverted exclamation mark-f][1,3,2]diazaborinin-4-ium-5-uide；2,2-difluoro-8-(4-iodophenyl)-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 1222084-15-2
• 化学式: C₁₅H₁₀BF₂IN₂
• 分子量: 393.97
• InChiKey: QAEPQQAHNCZYSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  4′′-bromobutyl-2α-propargyl-3β-hydroxylup-20(29)-ene-28-betulinoate 、 4,4-difluoro-8-(4-iodophenyl)-4-bora-3a,4a-diaza-s-indacene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80 %的产率得到4′′-bromobutyl-2α-propynyl-[3′-(4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-8-phenyl-yl)]-3β-hydroxylup-20(29)-ene-28-betulinoate
  参考文献：
  名称：

  侧链 C-28 末端三苯基膦​​基的 Bodipy 标记荧光桦木酸衍生物的合成

  摘要：

  开发了一种合成 BODIPY 标记的桦木酸衍生物的新方法，该衍生物的末端线粒体靶向侧链 C-28 上的三苯基膦基团。关键的合成步骤是桦木酸的 C-2 丙炔基衍生物与 BODIPY 平台的 C-2 或 C-8 上含有碘官能团的荧光染料衍生物的卤化物之间的交叉偶联。开发的 BODIPY 荧光团与桦木酸共价键合程序使天然 3-OH 和 28-COOH 基团能够保留在三萜核心中。

  DOI：

  10.1007/s10600-022-03869-6
• 作为产物：
  描述：

  4-碘苯甲醛 在 indium(III) chloride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 为溶剂， 反应 9.17h， 生成 4,4-difluoro-8-(4-iodophenyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  侧链 C-28 末端三苯基膦​​基的 Bodipy 标记荧光桦木酸衍生物的合成

  摘要：

  开发了一种合成 BODIPY 标记的桦木酸衍生物的新方法，该衍生物的末端线粒体靶向侧链 C-28 上的三苯基膦基团。关键的合成步骤是桦木酸的 C-2 丙炔基衍生物与 BODIPY 平台的 C-2 或 C-8 上含有碘官能团的荧光染料衍生物的卤化物之间的交叉偶联。开发的 BODIPY 荧光团与桦木酸共价键合程序使天然 3-OH 和 28-COOH 基团能够保留在三萜核心中。

  DOI：

  10.1007/s10600-022-03869-6

文献信息

• Iterative Arylation of Amino Acids and Aliphatic Amines via δ‐C(sp ³ )−H Activation: Experimental and Computational Exploration
  作者：Srimanta Guin、Pravas Dolui、Xinglong Zhang、Satyadip Paul、Vikas Kumar Singh、Sukumar Pradhan、Hediyala B. Chandrashekar、S. S. Anjana、Robert S. Paton、Debabrata Maiti

  DOI：10.1002/anie.201900479

  日期：2019.4.16

  mostly up to the γ‐position. In the present work, we demonstrate the diverse (hetero)arylation of amino acids and analogous aliphatic amines selectively at the remote δ‐position by tuning the reactivity controlled by ligands. An organopalladium δ‐C(sp3)−H activated intermediate has been isolated and crystallographically characterized. Mechanistic investigations carried out experimentally in conjunction

  定向C H功能化已实现为传统方法的补充工具，可直接访问非蛋白原性氨基酸。尽管这样的过程主要限于γ位置。在当前的工作中，我们通过调节配体控制的反应性，证明了在远端δ位选择性地使氨基酸和类似的脂肪族胺具有多种（杂）芳基化作用。已分离出有机钯δ-C（sp 3）-H活化中间体，并进行了晶体学表征。实验研究与计算研究相结合进行的机理研究揭示了取决于基材结构的机理图上的差异。
• Panchromatic Light Capture and Efficient Excitation Transfer Leading to Near‐IR Emission of BODIPY Oligomers
  作者：Ritambhara Sharma、Habtom B. Gobeze、Francis D'Souza、Mangalampalli Ravikanth

  DOI：10.1002/cphc.201600317

  日期：2016.8.18

  singlet–singlet energy transfer from BODIPY monomer to BODIPY dimer leading to emission in the 700–800 nm range. Theoretical modeling according to the Förster mechanism predicts ultrafast energy transfer due to good spectral overlap of the donor and acceptor entities. Femtosecond transient absorption studies confirm this to be the case and thus show the relevance of the currently developed all‐BODIPY‐based

  据报道，基于全BODIPY（BODIPY =硼二吡咯亚甲基）的供体-受体系统具有宽带吸收能力，可在近红外区域进行有效的能量转移。共价连接的3-吡咯基BODIPY-BODIPY二聚体积木轴承在乙炔基内消旋-芳基位置被合成和Pd下加上三种不同的单体BODIPY /吡咯基BODIPY积木用溴/碘基0偶联条件以19-29％的产率获得三个基于共价键的3-吡咯基-BODIPY的供体-受体低聚物。该低聚物的特征在于1D和2D NMR光谱，高分辨率质谱和光学光谱。由于低聚物中存在不同的功能化BODIPY衍生物，因此可以观察到全色光捕获（300–725 nm）。荧光研究表明，单重态-单重态能量从BODIPY单体转移到BODIPY二聚体，从而导致700-800 nm范围内的发射。根据Förster机制的理论建模预测，由于施主和受主实体的良好光谱重叠，超快的能量转移。
• An Amphiphilic BODIPY-Porphyrin Conjugate: Intense Two-Photon Absorption and Rapid Cellular Uptake for Two-Photon-Induced Imaging and Photodynamic Therapy
  作者：Tao Zhang、Rongfeng Lan、Longlong Gong、Baoyan Wu、Yuzhi Wang、Daniel W. J. Kwong、Wai-Kwok Wong、Ka-Leung Wong、Da Xing

  DOI：10.1002/cbic.201500349

  日期：2015.11

  dual‐purpose tumour‐imaging and PDT agent: The amphiphilic BODPY‐porphyrin conjugate BZnPP was synthesised and displayed a large two‐photon absorption cross‐section, a high singlet oxygen quantum yield and intense red emission. In vitro biological investigations showed that BZnPP exhibits very efficient tumour cellular uptake and two‐photon‐induced cell imaging and cytotoxicity.

  兼作肿瘤成像和PDT的两用剂：合成了两亲性BODPY-卟啉共轭物BZnPP，并显示出大的两光子吸收截面，高的单线态氧量子产率和强烈的红色发射。体外生物学研究表明，BZnPP表现出非常有效的肿瘤细胞摄取以及双光子诱导的细胞成像和细胞毒性作用。
• Scope and Limitations of the Liebeskind–Srogl Cross-Coupling Reactions Involving the Biellmann BODIPY
  作者：Lourdes Betancourt-Mendiola、Ismael Valois-Escamilla、Teresa Arbeloa、Jorge Bañuelos、Iñigo López Arbeloa、Juan O. Flores-Rizo、Rongrong Hu、Erik Lager、César F. A. Gómez-Durán、José L. Belmonte-Vázquez、Mayra R. Martínez-González、Ismael J. Arroyo、Carlos A. Osorio-Martínez、Enrique Alvarado-Martínez、Arlette Urías-Benavides、Brenda D. Gutiérrez-Ramos、Ben Zhong Tang、Eduardo Peña-Cabrera

  DOI：10.1021/acs.joc.5b00731

  日期：2015.6.5

  Several new examples of meso-(het)aryIBODIPY were prepared via the Liebeskind-Srogl (L-S) cross-coupling reaction of the Biellmann BODIPYs (1a,b) and aryl- and heteroarylboronic acids in good to excellent yield. It was shown that this reaction could be carried out under microwave heating to shorten reaction times and/or increase the yield. It was illustrated that organostannanes also participate in the L-S reaction to give the corresponding BODIPY analogues in short reaction times and also with good to excellent yields. We analyze the role of the substituent at the sensitive meso position in the photophysical signatures of these compounds. In particular, the rotational motion of the aryl ring and the electron donor ability of the anchored moieties rule the nonradiative pathways and, hence, have a deep impact in the fluorescence efficiency.
• Synthesis of boron-dipyrromethene–ferrocene conjugates
  作者：M. Rajeswara Rao、K.V. Pavan Kumar、M. Ravikanth

  DOI：10.1016/j.jorganchem.2010.01.009

  日期：2010.3

  Synthesis, spectral, electrochemical and photophysical properties of four BODIPY-ferrocene conjugates in which one or two ferrocenyl groups were covalently connected either directly to boron-dipyrromethene framework or to meso-phenyl group of boron-dipyrromethene unit are described. The BODIPY-ferrocene conjugates were prepared by adopting different synthetic routes. The absorption studies indicated the presence of charge transfer band in BODIPY-ferrocene conjugates in which the ferrocenyl group(s) were directly connected to boron-dipyrromethene framework. The electrochemical studies on conjugates indicated that ferrocenyl group was difficult to oxidize whereas boron-dipyrromethene unit was easier to reduce. The conjugates were non-fluorescent due to electron transfer from ferrocene to boron-dipyrromethene unit. However, when ferrocene was oxidized to ferrocenium ion with an oxidizing agent, the conjugates exhibited fluorescence with decent quantum yields (0.17-0.31) and lifetimes (3.8-5.2 ns). (C) 2010 Elsevier B.V. All rights reserved.