(Z)-3-ethyl-5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)(phenyl)methyl)-2,4-dimethyl-1H-pyrrole | 917201-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (Z)-3-ethyl-5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)(phenyl)methyl)-2,4-dimethyl-1H-pyrrole
• 英文别名: (2Z)-4-ethyl-2-[(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-phenylmethylidene]-3,5-dimethylpyrrole
• CAS: 917201-08-2
• 化学式: C₂₃H₂₈N₂
• 分子量: 332.489
• InChiKey: FWPSJYDQBNAFMB-LNVKXUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3-ethyl-5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)(phenyl)methyl)-2,4-dimethyl-1H-pyrrole 在 sodium hydroxide 、 氘代氯仿 、 氘代甲醇 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以40%的产率得到(Z)-3-ethyl-5-((4-ethyl-3,5(²H₃)-dimethyl-2H-pyrrol-2-ylidene)(phenyl)methyl)-2(²H₃),4-dimethyl-1²H-pyrrole
  参考文献：
  名称：

  Deuteration and tautomeric reactivity of the 1-methyl functionality of free-base dipyrrins

  摘要：

  自由基二吡啶的1-甲基基团的区域选择性反应被探讨，包括对互变异构体的讨论，以提供外环烯基反应性。

  DOI：

  10.1039/c7ob01278k
• 作为产物：
  描述：

  苯甲醛 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (Z)-3-ethyl-5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)(phenyl)methyl)-2,4-dimethyl-1H-pyrrole
  参考文献：
  名称：

  Use of F-BODIPYs as a Protection Strategy for Dipyrrins: Optimization of BF₂ Removal

  摘要：

  We recently reported the first general method for the deprotection of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) involving a microwave-assisted procedure for the removal of the BF2 moiety, and liberation of the corresponding free-base dipyrrin. Further optimization of the reaction has resulted in a more convenient and accessible protocol. The availability of this new methodology enables BF2-complexation to be used as a dipyrrin protection strategy. Herein lies a detailed examination of the deprotection reaction, with a view to optimization and gaining mechanistic insight, and its application in facilitating a multistep synthesis of pyrrolyldipyrrins.

  DOI：

  10.1021/jo3002003

文献信息

• Design and Development of a New Pyrromethene Dye with Improved Photostability and Lasing Efficiency:  Theoretical Rationalization of Photophysical and Photochemical Properties
  作者：Soumyaditya Mula、Alok K. Ray、Manas Banerjee、Tandrima Chaudhuri、Kamalesh Dasgupta、Subrata Chattopadhyay

  DOI：10.1021/jo702346s

  日期：2008.3.1

  In an attempt to develop a photostable and efficient pyrromethene compound for use in liquid dye lasers, three congeners of the commercially available pyrromethene 567 (PM567) laser dye were synthesized and their photophysical properties, lasing efficiencies, and photochemical stabilities were studied. In general the presence of an aryl group at C-8 of the pyrromethene chromophore increased the photostability

  为了开发一种用于液体染料激光器的光稳定有效的吡咯亚甲基化合物，合成了三种同类的市售吡咯烯567（PM567）激光染料，并对其光物理性质，激光发射效率和光化学稳定性进行了研究。通常，吡咯亚甲基生色团的C-8处芳基的存在增加了光稳定性。具有C-8三甲氧基苯基部分的同类物之一显示出比PM567显着改善的激射参数。与PM567相比，新染料的光化学稳定性是其2倍，而在显着较低的浓度下，其激光发射效率与PM567相当。1 O 2）和与1 O 2反应的可能性。我们的计算与实验结果相符，并表明系统设计新的吡咯亚甲基生色团衍生物可能会导致改进的激光染料分子。
• Highly Sensitive Fluorescence Probes for Nitric Oxide Based on Boron Dipyrromethene ChromophoreRational Design of Potentially Useful Bioimaging Fluorescence Probe
  作者：Yu Gabe、Yasuteru Urano、Kazuya Kikuchi、Hirotatsu Kojima、Tetsuo Nagano

  DOI：10.1021/ja037944j

  日期：2004.3.1

  4-diaminophenyl)-2,6-bis(2-carboxyethyl)-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (DAMBO-P(H)), based on the BODIPY chromophore, as a highly sensitive fluorescence probe for nitric oxide (NO). DAMBO-P(H) had a low phi value of 0.002, whereas its triazole derivative (DAMBO-P(H)-T), the product of the reaction of DAMBO-P(H) with NO, fluoresced strongly (phi = 0.74). The change of

  已知硼二吡咯甲烯 (BODIPY) 在水溶液中具有高荧光量子产率 (phi)，但与荧光素相比，在生物应用中的利用并不多。我们开发了 8-(3,4-diaminophenyl)-2,6-bis(2-carboxyethyl)-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s -indacene (DAMBO-P(H))，基于 BODIPY 发色团，作为一氧化氮 (NO) 的高灵敏度荧光探针。DAMBO-P(H) 具有 0.002 的低 phi 值，而其三唑衍生物 (DAMBO-P(H)-T)，即 DAMBO-P(H) 与 NO 反应的产物，发出强烈荧光（phi = 0.74 ）。发现荧光强度的变化受分子内光致电子转移（PeT）机制控制。DAMBO-P(H)的开发策略如下：（1）为了设计高灵敏度的NO探针，
• Heavy-Atom Free <i>spiro</i> Organoboron Complexes As Triplet Excited States Photosensitizers for Singlet Oxygen Activation
  作者：Paulina H. Marek-Urban、Mateusz Urban、Magdalena Wiklińska、Klaudia Paplińska、Krzysztof Woźniak、Agata Blacha-Grzechnik、Krzysztof Durka

  DOI：10.1021/acs.joc.1c01254

  日期：2021.9.17

  new strategy for the development of efficient heavy-atom free singlet oxygen photosensitizers based on rigid borafluorene scaffolds. Physicochemical properties of borafluorene complexes can be easily tuned through the choice of ligand, thus allowing exploration of numerous organoboron structures as potent 1O2 sensitizers. The singlet oxygen generation quantum yields of studied complexes vary in the range

  在此，我们提出了一种开发基于刚性硼芴支架的高效无重原子单线态氧光敏剂的新策略。硼芴配合物的物理化学性质可以通过配体的选择轻松调整，从而允许探索许多有机硼结构作为有效的1 O 2敏化剂。研究的复合物的单线态氧产生量子产率在 0.55-0.78 的范围内变化。理论计算表明，硼芴部分的引入对于单线态电荷转移态的稳定至关重要，而正交供体-受体分子结构促进了系统间跨越到局部三线态。我们的研究表明，只需 0.05 mol% 的光催化剂负载量，就可以在 20-120 分钟的照射时间内实现对选定有机底物的定量氧化。
• The first series of alkali dipyrrinato complexes
  作者：Adeeb Al-Sheikh Ali、Judy Cipot-Wechsler、Sarah M. Crawford、Omar Selim、Rhonda L. Stoddard、T. Stanley Cameron、Alison Thompson

  DOI：10.1139/v09-180

  日期：2010.8

  The first series of alkali dipyrrinato complexes is reported, encompassing lithium, sodium, and potassium salts of meso-unsubstituted and meso-aryl-substituted derivatives. By varying the substituents at the meso position, the intermolecular distance between the two nitrogen atoms and thus the κ²-N,N-bidentate bite angle was altered, as confirmed by comparison of crystallographic structures of dipyrrin free-bases in the solid-state. The mode of bonding varies as the ionic radius of the metal ion increases: solid-state structures reveal lithium to be accommodated in the plane of the dipyrrinato unit, whilst sodium is accommodated out of plane. The reactivity of analogous lithium, sodium, and potassium dipyrrinato complexes increases as the ionic radius of the metal ion increases, in keeping with the concept that the complexes tend towards an increasingly ionic nature as the size of the alkali metal increases.

  报告了第一个碱二吡咯烷酮配合物系列，包括中位未取代和中位芳基取代衍生物的锂、钠和钾盐。通过改变中位取代基，两个氮原子之间的分子间距发生了变化，从而改变了κ2-N,N-二齿咬合角，这一点通过比较二吡咯啉游离基在固态下的晶体结构得到了证实。成键模式随金属离子的离子半径增大而变化：固态结构显示锂被容纳在二吡咯烷单元的平面内，而钠则被容纳在平面外。类似的锂、钠和钾二吡咯烷酮络合物的反应性随着金属离子的离子半径的增加而增加，这与络合物的离子性随着碱金属尺寸的增加而增加这一概念是一致的。
• Conversion of 4,4-Difluoro-4-bora-3a,4a-diaza-<i>s</i>-indacenes <b>(</b><i>F</i>-BODIPYs) to Dipyrrins with a Microwave-Promoted Deprotection Strategy
  作者：Sarah M. Crawford、Alison Thompson

  DOI：10.1021/ol902908j

  日期：2010.4.2

  4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) have been deprotected to give the corresponding free-base dipyrrins by heating a solution of the F-BODIPY In tert-butanol under 600 W of microwave irradiation in the presence of 6 equiv of potassium tert-butoxide for 40 min at 92 degrees C. Investigations of BODIPY modification at the meso position have also been undertaken and a meso-butyl product has been isolated.