2,3-diphenyl-5,8-diiodoquinozaline | 144792-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-diphenyl-5,8-diiodoquinozaline
• 英文别名: 2,3-diphenyl-5,8-diiodoquinoxaline；5,8-Diiodo-2,3-diphenylquinoxaline
• CAS: 144792-96-1
• 化学式: C₂₀H₁₂I₂N₂
• 分子量: 534.138
• InChiKey: DHVGALGQIZVAPQ-UHFFFAOYSA-N

物化性质

• 沸点：
  534.6±45.0 °C(Predicted)
• 密度：
  1.876±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-diphenyl-5,8-diiodoquinozaline 在 bis-triphenylphosphine-palladium(II) chloride 盐酸 、 sodium hydride 、 lead dioxide 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 生成 2,3-diphenyl-5H,8H-5,8-bis(dicyanomethylene)quinoxaline
  参考文献：
  名称：

  Single-component organic conductors based on neutral radicals containing the pyrazino-TCNQ skeleton

  摘要：

  Pyrazino-TCNQ (1a) prepared from 5,8-diiodoquinoxaline (4a) is, like TCNQ itself, a strong electron acceptor and gives a stable anion radical salt as well as highly conductive charge-transfer crystals with donors. Substituted derivatives 1b-i were similarly prepared from 3,6-diiodo-1,2-phenylenediamine (5) as a common intermediate, and bulky substituents such as the phenyl or pyridyl groups have very little effect on either the redox properties or planar geometry of la. Neutral radicals 3d-g derived from pyridyl-substituted derivatives 1d-g, respectively, are open-shell donor-pi-acceptor systems with high electrical amphotericity designed as a new motif for single-component organic conductors. The powder conductivity of 3f was as high as 3.2 X 10(-5) S cm-1.

  DOI：

  10.1021/jo00051a015
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 在 盐酸 、 sodium tetrahydroborate 、 copper(l) iodide 、 selenium(IV) oxide 、 potassium iodide 、 tin(ll) chloride 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 73.5h， 生成 2,3-diphenyl-5,8-diiodoquinozaline
  参考文献：
  名称：

  Single-component organic conductors based on neutral radicals containing the pyrazino-TCNQ skeleton

  摘要：

  Pyrazino-TCNQ (1a) prepared from 5,8-diiodoquinoxaline (4a) is, like TCNQ itself, a strong electron acceptor and gives a stable anion radical salt as well as highly conductive charge-transfer crystals with donors. Substituted derivatives 1b-i were similarly prepared from 3,6-diiodo-1,2-phenylenediamine (5) as a common intermediate, and bulky substituents such as the phenyl or pyridyl groups have very little effect on either the redox properties or planar geometry of la. Neutral radicals 3d-g derived from pyridyl-substituted derivatives 1d-g, respectively, are open-shell donor-pi-acceptor systems with high electrical amphotericity designed as a new motif for single-component organic conductors. The powder conductivity of 3f was as high as 3.2 X 10(-5) S cm-1.

  DOI：

  10.1021/jo00051a015

文献信息

• From Quinoxaline, Pyrido[2,3-b]pyrazine and Pyrido[3,4-b]pyrazine to Pyrazino-Fused Carbazoles and Carbolines
  作者：Frédéric Lassagne、Timothy Langlais、Elsa Caytan、Emmanuelle Limanton、Ludovic Paquin、Manon Boullard、Coline Courtel、Idriss Curbet、Clément Gédéon、Julien Lebreton、Laurent Picot、Valérie Thiéry、Mohamed Souab、Blandine Baratte、Sandrine Ruchaud、Stéphane Bach、Thierry Roisnel、Florence Mongin

  DOI：10.3390/molecules23112961

  日期：——

  2,3-Diphenylated quinoxaline, pyrido[2,3-b]pyrazine and 8-bromopyrido[3,4-b]pyrazine were halogenated in deprotometalation-trapping reactions using mixed 2,2,6,6-tetramethyl piperidino-based lithium-zinc combinations in tetrahydrofuran. The 2,3-diphenylated 5-iodo- quinoxaline, 8-iodopyrido[2,3-b]pyrazine and 8-bromo-7-iodopyrido[3,4-b]pyrazine thus obtained were subjected to palladium-catalyzed couplings

  2,3-二苯基喹喔啉、吡啶并[2,3-b]吡嗪和8-溴吡啶并[3,4-b]吡嗪在脱金属捕集反应中使用混合2,2,6,6-四甲基哌啶基锂被卤化-四氢呋喃中的锌组合。由此获得的2,3-二苯基化5-碘-喹喔啉、8-碘吡啶并[2,3-b]吡嗪和8-溴-7-碘吡啶并[3,4-b]吡嗪与芳基硼酸进行钯催化偶联。酸或苯胺，以及可能的后续环化以提供相应的吡嗪并[2,3-a]咔唑、吡嗪并[2',3':5,6]吡啶并[4,3-b]吲哚和吡嗪并[2',3] ':4,5]吡啶并[2,3-d]吲哚。8-碘吡啶并[2,3-b] 吡嗪经过铜催化与唑类形成CN 键，或直接取代以在8 位引入烷基氨基、苄氨基、肼和芳氧基。8-肼产物转化为芳基腙。对大多数化合物的生物学特性（A2058 黑色素瘤细胞的抗增殖活性和疾病相关激酶抑制作用）进行了评估。
• Synthesis and characterisation of new acetylide-functionalised aromatic and hetero-aromatic ligands and their dinuclear platinum complexes
  作者：Muhammad S. Khan、Mohammed K. Al-Suti、Muna R. A. Al-Mandhary、Birte Ahrens、Jens K. Bjernemose、Mary F. Mahon、Louise Male、Paul R. Raithby、Richard H. Friend、Anna Köhler、Joanne S. Wilson

  DOI：10.1039/b208494e

  日期：——

  A new series of rigid rod protected and terminal dialkynes with extended π-conjugation through aromatic and hetero-aromatic linker units in the backbone, 2,5-bis(trimethylsilylethynyl)-1-(2-ethylhexyloxy)-4-methoxybenzene 1a, 2,5-bis(ethynyl)-1-(2-ethylhexyloxy)-4-methoxybenzene 1b, 5,8-bis(trimethylsilylethynyl)quinoline 2a, 5,8-bis(ethynyl)quinoline 2b, 2,3-diphenyl-5,8-bis(trimethylsilylethynyl)quinoxaline 3a, 2,3-diphenyl-5,8-bis(ethynyl)quinoxaline 3b, 4,7-bis(trimethysilylethynyl)-2,1,3-benzothiadiazole 4a and 4,7-bis(ethynyl)-2,1,3-benzothiadiazole 4b, has been synthesised. Treatment of the complex trans-[Pt(Ph)(Cl)(Et3P)2] with half an equivalent of the diterminal alkynes 1b–4b in iPr2NH–CH2Cl2, in the presence of CuI, at room temperature, afforded the platinum(II) di-yne complexes trans-[(Et3P)2(Ph)Pt–CC–R–CC–Pt(Ph)(Et3P)2] [R = 1-(2-ethylhexyloxy)-4-methoxybenzene-2,5-diyl 1c, quninoline-5,8-diyl 2c, 2,3-diphenylquinoxaline-5,8-diyl 3c, 2,1,3-benzothiadiazole-4,7-diyl 4c] in good yields. The new acetylide-functionalised ligands and the platinum(II) σ-acetylide complexes have been characterised by analytical and spectroscopic methods and X-ray single crystal structure determinations for 2c–4c. The absorption spectra of the complexes 2c–4c show substantial donor–acceptor interaction between the platinum(II) centres and the conjugated ligands. The photoluminescence spectra of 1c–3c show characteristic singlet (S1) and triplet (T1) emissions. Both the singlet and triplet emissions as well as the absorption decrease in energy with increasing electronegativity of the spacer groups along the series 1c–4c.

  8-双(三甲基硅乙炔基)喹啉 2a、5,8-双(乙炔基)喹啉 2b、2,3-二苯基-5,8-双(三甲基硅乙炔基)喹喔啉 3a、2,3-二苯基-5、合成了 2,3-二苯基-5,8-双（乙炔基）喹喔啉 3a、2,3-二苯基-5,8-双（乙炔基）喹喔啉 3b、4,7-双（三甲基硅乙炔基）-2,1,3-苯并噻二唑 4a 和 4,7-双（乙炔基）-2,1,3-苯并噻二唑 4b。在室温下，在 CuI 的存在下，在 iPr2NH-CH2Cl2 中将反式-[Pt(Ph)(Cl)(Et3P)2] 复合物与半当量的二端炔 1b-4b 进行处理、得到了反式-[(Et3P)2(Ph)Pt-CC-R-CC-Pt(Ph)(Et3P)2][R = 1-(2-乙基己氧基)-4-甲氧基苯-2,5-二基 1c、喹啉-5,8-二基 2c、2,3-二苯基喹喔啉-5,8-二基 3c、2,1,3-苯并噻二唑-4,7-二基 4c]的铂(II)二炔配合物，产率良好。新的乙酰功能化配体和铂(II)σ-乙酰配合物的特征已通过分析和光谱方法以及 2c-4c 的 X 射线单晶结构确定。配合物 2c-4c 的吸收光谱显示，铂（II）中心与共轭配体之间存在大量的供体-受体相互作用。1c-3c 的光致发光光谱显示出特征性的单线（S1）和三线（T1）发射。随着 1c-4c 系列中间隔基团电负性的增加，单线和三线发射以及吸收的能量都会降低。
• Single-component organic conductors based on neutral radicals containing the pyrazino-TCNQ skeleton
  作者：Yoshiaki Tsubata、Takanori Suzuki、Tsutomu Miyashi、Yoshiro Yamashita

  DOI：10.1021/jo00051a015

  日期：1992.12

  Pyrazino-TCNQ (1a) prepared from 5,8-diiodoquinoxaline (4a) is, like TCNQ itself, a strong electron acceptor and gives a stable anion radical salt as well as highly conductive charge-transfer crystals with donors. Substituted derivatives 1b-i were similarly prepared from 3,6-diiodo-1,2-phenylenediamine (5) as a common intermediate, and bulky substituents such as the phenyl or pyridyl groups have very little effect on either the redox properties or planar geometry of la. Neutral radicals 3d-g derived from pyridyl-substituted derivatives 1d-g, respectively, are open-shell donor-pi-acceptor systems with high electrical amphotericity designed as a new motif for single-component organic conductors. The powder conductivity of 3f was as high as 3.2 X 10(-5) S cm-1.