1-(thiophen-2-yl)isoquinoline | 435278-01-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(thiophen-2-yl)isoquinoline
• 英文别名: 1-(Thien-2-yl)isoquinoline；1-thiophen-2-ylisoquinoline
• CAS: 435278-01-6
• 化学式: C₁₃H₉NS
• 分子量: 211.287
• InChiKey: CHTCOKFKFBSPGI-UHFFFAOYSA-N

物化性质

• 熔点：
  67-69 °C
• 沸点：
  345.4±22.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(thiophen-2-yl)isoquinoline 以 甲醇 、 二氯甲烷 、 乙二醇甲醚 、 水 为溶剂， 反应 25.0h， 生成 [Ir(1-(2-thiophenyl)isoquinoline)₂(2,2'-bipyridine)][PF₆]
  参考文献：
  名称：

  2‐thiophenyl‐isoquinoline Ir(III) complex as red absorbing photosensitizer: a promising tool in antipseudomonal photodynamic therapy

  摘要：

  Innovative therapeutic strategies are more than ever needed to counter the rise of antibiotic‐resistant bacterial pathogens worldwide. The use of light, and especially photodynamic therapy (PDT) appears as a promising alternative or complement to antibiotic treatments, fostered by the development of new photosensitizers. In this study, eight luminescent Ir(III) complexes were synthesized and evaluated for their photoactivation properties and capacity to generate radical species under blue (452 nm), green (525 nm), and red (631 nm) LED light, respectively. Their antibacterial properties were assessed on Pseudomonas aeruginosa, Acinetobacter baumannii, Escherichia coli, and Staphylococcus aureus with most of these complexes exhibiting potentially useful activities upon light irradiation, at concentrations below 10 mg/L. A complex of Ir(III) cyclometallated to thiophenyl‐isoquinoline (tiq) and bearing 2,2’‐bipyridine (bipy) as ancillary ligand was further investigated. This latter showed a concentration‐ and light intensity‐dependent bactericidal activity on P. aeruginosa when irradiated under blue to red lights, proving that such complexes would be suitable candidates for PDT. Importantly, this lead complex remained active against antibiotic resistant clinical strains and was unaffected by active efflux systems. These data open interesting perspectives for the development of new treatments to tackle antibiotic resistant Gram‐negative bacteria.

  DOI：

  10.1002/ejic.202300767
• 作为产物：
  描述：

  1-(thiophen-2-yl)-3H-benzo[c]azepin-3-one 在 盐酸 、 三氯异氰尿酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.02h， 生成 1-(thiophen-2-yl)isoquinoline
  参考文献：
  名称：

  氨基脱芳构化引发萘酚骨架的多样化

  摘要：

  银催化的萘酚氨基脱芳构化反应已被开发出来，并整合到逐步的方法中，用于随后的骨架多样化，包括扩环、开环、收缩和芳基支架的原子嬗变。这种方法能够从萘酚底物合成多种氮杂酮、不饱和酰胺、异喹啉和茚酮。其在生物活性和功能分子的合成以及复杂分子骨架的转化中的应用强调了其广泛的潜在适用性。机理研究表明脱芳构化中间体的中间作用。

  DOI：

  10.1021/acs.orglett.4c01416

文献信息

• Highly Efficient Monophosphine-Based Catalyst for the Palladium-Catalyzed Suzuki−Miyaura Reaction of Heteroaryl Halides and Heteroaryl Boronic Acids and Esters
  作者：Kelvin Billingsley、Stephen L. Buchwald

  DOI：10.1021/ja068577p

  日期：2007.3.1

  active and efficient catalyst system derived from a palladium precatalyst and monophosphine ligands 1 or 2 for the Suzuki-Miyaura cross-coupling reaction of heteroaryl boronic acids and esters has been developed. This method allows for the preparation of a wide variety of heterobiaryls in good to excellent yields and displays a high level of activity for the coupling of heteroaryl chlorides as well as

  已经开发了一种高活性和高效的催化剂体系，该体系源自钯预催化剂和单膦配体 1 或 2，用于杂芳基硼酸和酯的 Suzuki-Miyaura 交叉偶联反应。该方法允许以良好到优异的产率制备多种杂二芳基化合物，并且对于杂芳基氯化物以及受阻芳基和杂芳基卤化物的偶联显示出高水平的活性。还研究了控制某些杂环基序转化效率的特定因素。
• NOVEL ORGANIC HETEROCYCLIC COMPOUND AND LIGHT-EMITTING DEVICE COMPRISING SAME
  申请人：SFC CO., LTD.

  公开号：US20180072753A1

  公开（公告）日：2018-03-15

  The present invention relates to an organic light-emitting compound represented by [Chemical Formula A] and an organic light-emitting device. In Chemical Formula, A, X, Y, Z, and the substituents R 1 to R 8 , and R 11 to R 20 are as defined in the specification.

  本发明涉及一种由[化学公式A]表示的有机发光化合物以及一种有机发光器件。在化学公式中，A、X、Y、Z以及取代基R1至R8和R11至R20如说明书中所定义。
• Homoleptic Cyclometalated Iridium Complexes with Highly Efficient Red Phosphorescence and Application to Organic Light-Emitting Diode
  作者：Akira Tsuboyama、Hironobu Iwawaki、Manabu Furugori、Taihei Mukaide、Jun Kamatani、Satoshi Igawa、Takashi Moriyama、Seishi Miura、Takao Takiguchi、Shinjiro Okada、Mikio Hoshino、Kazunori Ueno

  DOI：10.1021/ja034732d

  日期：2003.10.1

  = 558-652 nm, and emission lifetimes tau = 0.74-4.7 micros. Bathochromic shifts of the Ir(thpy)(3) family [the complexes with 2-(thiophen-2-yl)pyridine derivatives] are observed by introducing appropriate substituents, e.g., methyl, trifluoromethyl, or thiophen-2-yl. However, Phi(p) of the red emissive complexes (lambda(max) > 600 nm) becomes small, caused by a significant decrease of the radiative

  已经进行了一系列面部均质环金属化铱 (III) 配合物的磷光研究。所研究的配合物具有一般结构 Ir(III)(CN)(3)，其中 (CN) 是单阴离子环金属化配体：2-(5-methylthiophen-2-yl)pyridinato, 2-(thiophen-2-yl) -5-三氟甲基吡啶基，2,5-二(噻吩-2-基)吡啶基，2,5-二(5-甲基噻吩-2-基)吡啶基，2-(苯并[b]噻吩-2-基)吡啶基， 2-(9,9-二甲基-9H-芴-2-基)吡啶基、1-苯基异喹啉基、1-(噻吩-2-基)异喹啉基或1-(9,9-二甲基-9H-芴-2-基)异喹啉。所有配合物在 298 K 甲苯中的发光特性如下：磷光量子产率 Phi(p) = 0.08-0.29，发射峰 lambda(max) = 558-652 nm，发射寿命 tau = 0.74-4.7 微米。通过引入适当的取代基，例如甲基、三氟甲基或噻吩-2-基，可以观察到
• METALLIC COMPOUND AND ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING THE SAME
  申请人：Suh Dong-Hack

  公开号：US20090326236A1

  公开（公告）日：2009-12-31

  The present invention relates to a light emitting binuclear transition metal compound of Chemical Formulae 1 and 2, and an organic electroluminescence device including the compound. In the Chemical Formulae 1 and 2, M is selected from Ir, Pt, Rh, Re, and Os, and m is 2, provided that the m is 1 when M is Pt.

  本发明涉及化学式1和2的发光双核过渡金属化合物，以及包括该化合物的有机电致发光器件。在化学式1和2中，M选自Ir、Pt、Rh、Re和Os，m为2，当M为Pt时，m为1。
• Metallic Compound and Organic Electroluminescence Device Comprising the Same
  申请人：Suh Dong-Hack

  公开号：US20080269484A1

  公开（公告）日：2008-10-30

  The present invention relates to a light emitting metallic compound of Chemical Formula 1 and an organic electroluminescence device including the compound. In the Chemical Formula 1, M is selected from Ir, Pt, Rh, Re, and Os, and m is 2, provided that m is 1 when M is Pt.

  本发明涉及一种化学式1的发光金属化合物和包括该化合物的有机电致发光器件。在化学式1中，M从Ir、Pt、Rh、Re和Os中选择，m为2，当M为Pt时，m为1。