2,4-di(trifluoromethyl)-7-phenylaminoquinoline | 1345323-05-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,4-di(trifluoromethyl)-7-phenylaminoquinoline
• 英文别名: 2,4-Bis(trifluoromethyl)-N-phenyl-7-quinolineamine；N-phenyl-2,4-bis(trifluoromethyl)quinolin-7-amine
• CAS: 1345323-05-8
• 化学式: C₁₇H₁₀F₆N₂
• 分子量: 356.27
• InChiKey: NPWZMUWHIPTQLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,4-di(trifluoromethyl)-7-phenylaminoquinoline 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 2,4-bis(trifluoromethyl)-7H-pyrido[3,2-c]carbazole
  参考文献：
  名称：

  发射性吡啶并[3,2-c]咔唑衍生物的光物理性质和细胞凋亡诱导：响应光刺激而向理疗药物的发展。

  摘要：

  吡唑并咔唑部分存在于许多天然产物中，例如奥利福因和玫瑰树碱，并且它们的衍生物是众所周知的抗癌剂。为了开发功能性的治疗和诊断化合物，使用钯配合物作为催化剂，从氨基喹啉衍生物合成了三种含仲或叔胺基团的发射性吡啶并[3,2-c]咔唑衍生物PC-X。X射线衍射分析表明，PC-X在吡啶环和咔唑骨架之间显示出高度平面的结构，具有高荧光强度以及溶剂变色行为。用PC-X处理的HeLa细胞的成像显示没有特异性积累到细胞器中。然而，一项比较检查表明，与细胞核和溶酶体相比，线粒体中的积累最高。使用HeLa细胞进行的细胞毒性分析表明，与另一个具有叔胺基的PC-X相比，包含仲胺基的PC-H具有最高的细胞毒性（IC50≈20μm）。与典型的线粒体染色剂MitoTracker的共定位显示出类似细胞凋亡的行为，并在近紫外光（403 nm）照射过程中出现明显的起泡现象，这表明PC-H不仅可以充当成像细胞器的荧光探针，而且还

  DOI：

  10.1002/asia.201901200
• 作为产物：
  描述：

  六氟乙酰丙酮 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 2,4-di(trifluoromethyl)-7-phenylaminoquinoline
  参考文献：
  名称：

  QUINOLINE COMPOUND

  摘要：

  提供的是一种固体发光喹啉化合物，能够在晶体状态下发光，能够改变发光颜色而无需修改分子构型，并能够对外部压力（如热、物理压力等）做出发光反应。喹啉化合物由以下一般式（1）表示：其中R1可以相同也可以不同，分别代表CF3或CF3CF2中的任意一种；R2代表氨基、N,N-二甲基氨基、N-苯基氨基、咔唑基、N-甲基氨基或N-甲基-N-苯基氨基中的任意一种。

  公开号：

  US20110263861A1

文献信息

• QUINOLINE COMPOUND
  申请人：Koga Noboru

  公开号：US20110263861A1

  公开（公告）日：2011-10-27

  Provided is a solid luminescent quinoline compound capable of emitting light in a crystalline state, capable of changing the luminescent color not requiring modification of molecular configuration and capable of emitting light in response to external pressure such as heat, physical pressure, etc. The quinoline compound is represented by the following general formula (1): wherein R 1 may be the same or different, each representing any of CF 3 or CF 3 CF 2 ; R 2 represents any of an amino group, an N,N-dimethylamino group, an N-phenylamino group, a carbazole group, an N-methylamino group or an N-methyl-N-phenylamino group.

  提供的是一种固体发光喹啉化合物，能够在晶体状态下发光，能够改变发光颜色而无需修改分子构型，并能够对外部压力（如热、物理压力等）做出发光反应。喹啉化合物由以下一般式（1）表示：其中R1可以相同也可以不同，分别代表CF3或CF3CF2中的任意一种；R2代表氨基、N,N-二甲基氨基、N-苯基氨基、咔唑基、N-甲基氨基或N-甲基-N-苯基氨基中的任意一种。
• Crystal Structures and Emitting Properties of Trifluoromethylaminoquinoline Derivatives: Thermal Single-Crystal-to-Single-Crystal Transformation of Polymorphic Crystals That Emit Different Colors
  作者：Yuichiro Abe、Satoru Karasawa、Noboru Koga

  DOI：10.1002/chem.201201213

  日期：2012.11.19

  crystalline state, TFMAQ derivatives emitted at longer wavelengths (=464–530 nm) with lower intensity (Φf(c)=0.01–0.28) than those in n‐hexane solution. The polymorphous crystals of 2 and 3 emitted different colors: 2, =470 and 530 nm with Φf(c)=0.04 and approximately 0.01 for crystal GB and YG, respectively; and 3, =464 and 506 nm with Φf(c)=0.28 and approximately 0.28 for crystal B and G, respectively

  制备并结晶了在喹啉环的7位具有胺（1），甲胺（2），苯胺（3）和二甲胺（4）取代基的2,4-三氟甲基喹啉（TFMAQ）衍生物。获得了六种晶体，包括2（GB和YG晶体）和3（B和G晶体）的多晶型物，并通过X射线晶体学对其进行了表征。在溶液中，TFMAQ衍生物发射的相对强的荧光（= 418-469纳米和Φ ˚F（S）= 0.23-0.60）取决于溶剂的极性。从利珀特-又贺图，Δ μ获得的值在7.8–14 D范围内。在结晶状态，TFMAQ衍生物在较长波长（发射= 464-530纳米）与较低强度（Φ ˚F比在（C）= 0.01-0.28）ñ -己烷溶液。的多晶型晶体2和3发射不同的颜色：2，= 470和具有530纳米Φ ˚F（C）= 0.04和用于分别晶体GB和YG，大约0.01; 和3，= 464及与506纳米Φ ˚F（C）= 0.28和0.28左右分别晶体B和G，。在2和3的两种晶型中，晶体G
• Acid responsiveness of emissive morpholinyl aminoquinolines and their use for cell fluorescence imaging
  作者：Yuri Fukumoto、Tomohiro Umeno、Hina Kuramochi、Koichi Hamada、Shota Matsumoto、Noriko Suzuki、Kazuteru Usui、Akihiro Mizutani、Satoru Karasawa

  DOI：10.1039/d2ob00546h

  日期：——

  The alkylmorpholine group is well-known to favor accumulation in lysosomes, but the TFMAQ derivatives containing ethylmorpholine groups only showed limited accumulation in lysosomes and, instead, preferential accumulation in lipid droplets.

  烷基吗啡环类化合物已被广泛认知有利于在溶酶体中积累，但含有乙基吗啡环的TFMAQ衍生物仅在溶酶体中显示有限的积累，反而更倾向于在脂滴中积累。
• Regioselective Photocyclizations of Di(quinolinyl)arylamines and Tri(quinolinyl)amine with Emission Color Changes and Photoreaction-Induced Self-Assemblies
  作者：Satoru Karasawa、Jun-ichi Todo、Kazuteru Usui、Naomi Harada、Kenji Yoza、Hiroshi Suemune、Noboru Koga

  DOI：10.1002/chem.201600514

  日期：2016.6.1

  Bis[2,4‐di(trifluoromethyl)quinoline‐7‐yl]amine (1), bis[2,4‐di(trifluoromethyl)quinoline‐7‐yl]methylamine (2), bis[2,4‐di(trifluoromethyl)quinoline‐7‐yl]phenylamine derivatives, Q2NPhX; X=NO2 (3 a), I (3 b), H (3 c), OMe (3 d), and NH2 (3 e), tris[2,4‐di(trifluoromethyl)quinoline‐7‐yl]amine (4), and bis[2,4‐di(pentafluoroethyl)quinoline‐7‐yl]‐4‐nitrophenylamine (5) were prepared as functional fluorophores

  双[2,4-二（三氟甲基）喹啉-7-基]胺（1），双[2,4-二（三氟甲基）喹啉-7-基]甲胺（2），双[2,4-二（三氟甲基）喹啉-7-基]苯胺衍生物，Q 2 NPhX；X = NO 2（3 a），I（3 b），H（3 c），OMe（3 d）和NH 2（3 e），tris [2,4-di（trifluoromethyl）quinoline-7yl制备了]胺（4）和双[2,4-二（五氟乙基）喹啉-7-基] -4-硝基苯胺（5）作为功能性荧光团。辐照溶液样品时，1没有明显变化，而2，3 a – d和4显示发射颜色从黄绿色变为蓝色，表明发生了光反应。基于吸收和发射光谱，1 H NMR光谱和X射线晶体学对光产物进行的分析表明，光环化反应在区域选择性和定量发生，从而形成弯曲的二吡啶并咔唑。在3 a – d中，反应速率取决于溶剂极性和苯环上的取代基。随着溶剂极性的降低和取代基吸电子特性的增强，光反应
• Crystal Structures, Thermal Properties, and Emission Behaviors of <i>N</i>,<i>N</i>-R-Phenyl-7-amino-2,4-trifluoromethylquinoline Derivatives: Supercooled Liquid-to-Crystal Transformation Induced by Mechanical Stimuli
  作者：Satoru Karasawa、Ryusuke Hagihara、Yuichiro Abe、Naomi Harada、Jun-ichi Todo、Noboru Koga

  DOI：10.1021/cg5001842

  日期：2014.5.7

  N,N-R-Phenyl-7-amino-2,4-trifluoromethylquinoline derivatives (R = Me (1), Et (2), isopropyl (3), and Ph (4)) were prepared as a new type of fluorophore responsive to external stimuli. 1, 2, 3, and 4 were obtained as single crystals including three crystal polymorphs (1 alpha, 1 beta, and 1 gamma) of 1 and two (2 alpha and 2 beta) of 2. In 4, a phase transition from 4(173) and 4(90) between 173 and 90 K was observed. The solid-state emission showed a red shift by 30-58 nm compared with the emission in n-hexane, and their emission properties depended on the molecular arrangements. The modes of molecular arrangements for 1 alpha, 1 beta, and 1 gamma were a slipped parallel (SP), head-to-tail gamma-type herringbone (HT-gamma-HB), and head-to-head gamma-type herringbone (HH-gamma-HB); those for 2 alpha and 2 beta were HT-gamma-HB and head-to-tail dimer (HT-dimer), and that for 3 was head-to-tail columnar (HTC). 4(173) and 4(90) were similar HT-gamma-HB. The crystal-to-crystal transformations from 1 gamma to 1 beta and from 2 beta to 2 alpha were observed by heating and grinding the crystal, respectively, with emittance changes. After melting, on cooling, all crystals formed supercooled liquid (SCL) and then glass states. In the SCL state, molecules were amorphous and were quickly crystallized by a mechanical stimulus such as scratching. By taking advantage of the difference of emitting intensity between the SCL and the crystal states for 1, "writing" and "erasing" of a letter with scratching and heating, respectively, were demonstrated.