1,4-dithiino[2,3-c:5,6-c']diquinoline | 50634-27-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,4-dithiino[2,3-c:5,6-c']diquinoline
• 英文别名: thioquinanthrene；Thiochinanthren；2,13-dithia-10,21-diazapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),3(12),4,6,8,10,15,17,19,21-decaene
• CAS: 50634-27-0
• 化学式: C₁₈H₁₀N₂S₂
• 分子量: 318.423
• InChiKey: KZQKWVYWXKNYAO-UHFFFAOYSA-N

物化性质

• 熔点：
  314-315 °C
• 沸点：
  553.4±38.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-dithiino[2,3-c:5,6-c']diquinoline 在 氯 、 溶剂黄146 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 4-(diethylamino)-N,N-diethylquinoline-3-sulfonamide
  参考文献：
  名称：

  Synthesis and Amination of 4-Chloro-3-quinolinesulfonyl Chloride

  摘要：

  Chlorinolysis of 4-chloro-3-benzylthioquinoline (2) or thioquinanthrene (1) using chlorine gas in the presence of water gave 4-chloro-3-quinolinesulfonyl chloride (3). Amination of (3) performed in ether led to 4-chloro-3-quinolinesulfonamides (4). Reactions of compound (3) with an excess of primary or secondary amine in two phase (water/toluene or benzene) system gave 4-(substituted amino)-3-quinolinesulfonamides (5) with two identical amine rests. While 4-chloro-3-quinolinesulfonamides (4) were aminated with an excess of amine into aminosulfonamides (5) with two identical or two various amine rests.

  DOI：

  10.3987/com-94-6683
• 作为产物：
  描述：

  喹啉 在 sulfur 作用下， 生成 1,4-dithiino[2,3-c:5,6-c']diquinoline
  参考文献：
  名称：

  5,12-Di(1-alkyl)thioquinanthrenediinium Bis-salts and 1-Alkyl-3-alkylthio-1,4-dihydro-4-thiooxoquinolines

  摘要：

  The preparation of 5,12-di(1-alkyl)thioquinanthrenediinium bis-salts and their transformation into 1-alkyl-3-alkylthio-1,4-dihydro-4-thiooxoquinolines are described.

  DOI：

  10.3987/com-90-5612

文献信息

• Synthesis, spectroscopic structure identification, X-ray study and anticancer activities of new angularly fused quinobenzothiazines
  作者：K. Pluta、M. Szmielew、K. Suwińska、M. Latocha

  DOI：10.1016/j.molstruc.2016.05.082

  日期：2016.10

  2D NMR (NOESY, COSY, HSQC and HMBC) spectra which enabled to distinguish the isomers and to exclude retro-Smiles rearrangement and the azine nitrogen atom alkylation pathways. This supposition was fully confirmed by X-ray analysis showing the quinobenzothiazine system to be folded and the substituent at the thiazine nitrogen atom in an equatorial position. Some compounds exhibited anticancer activity

  摘要 基于二氯二喹啉二硫化物和二喹啉二噻英与取代苯胺的反应，合成了 16 种新型四环角稠合氮杂吩噻嗪、8-、9- 和 10-取代的喹并苯并-1,4-噻嗪（苯并[a]-3-氮杂吩噻嗪）。与对氟苯胺和对甲硫基苯胺的反应仅产生一种产物，而与间三氟甲基苯胺的反应产生异构化合物。得到的8-10-取代的12H-醌苯并噻嗪通过噻嗪氮原子的烷基化进一步转化为12-取代的衍生物。结构分析基于 1D 和 2D NMR（NOESY、COSY、HSQC 和 HMBC）光谱，其能够区分异构体并排除逆向微笑重排和吖嗪氮原子烷基化途径。该假设通过 X 射线分析得到充分证实，显示出喹苯并噻嗪系统被折叠并且噻嗪氮原子上的取代基位于赤道位置。一些化合物对 MCF-7、MDA-MB-231 和 SNB-19 细胞系表现出抗癌活性，类似于参考药物顺铂。讨论了化合物的构效关系。
• 4-Alkoxy-3′-(alkylthio)-3,4′-diquinolinyl sulfides and 4-alkoxy-3-(alkylthio) quinolines
  作者：Andrzej Maślankiewicz、Stanistaw Boryczka

  DOI：10.1002/recl.19931121002

  日期：——

  The reactions of thioquinanthrene (1) with sodium alkoxides derived from 23 alcohols followed by S-alkylation gave the title 4-alkoxy-3′-(alkylthio)-3,4′-diquinolinyl sulfides 3 (18.5–91.5%) and, in some cases, 1,4-dihydro-4-oxo-3′-(alkylthio)-3,4′-diquinolinyl sulfides 4a (up to 31.5%). The effect of the solvent applied, counter-cation used and type of the alkyl group of alkoxide ions was then studied

  硫代蒽（1）与23种醇衍生的醇钠的反应，然后进行S-烷基化，得到标题4-烷氧基-3'-（烷硫基）-3,4'-二喹啉基硫化物3（18.5–91.5％），在某些情况下，为1,4-二氢-4-氧代-3'-（烷硫基）-3,4'-二喹啉基硫化物4a（最多31.5％）。然后通过竞争反应研究了所用溶剂，所用抗衡阳离子和烷氧基离子烷基类型的影响。有效地将4-烷氧基-3'-（烷硫基）-3,4'-二喹啉基硫化物3转化为约4个烷氧基-和4-（烷硫基）-3-（烷硫基）喹啉（5,6）和一锅还介绍了从硫代蒽（1）和烷醇钠制备4-烷氧基-3-（烷硫基）喹啉5的方法。
• Homolytic alkylation of some 3,4‐quinolinediyl bis‐sulfides under minisci reaction conditions
  作者：Andrzej Maślankiewicz、Ewa Michalik、Zbigniew Ciunik

  DOI：10.1002/jhet.5570450235

  日期：2008.3

  Reaction of hydrogen sulfate of 3,4-quinolinediyl bis-sulfides 1a, 2a, 3a, and 4a with isopropyl and cyclohexyl radicals formed from alkyl iodide/hydrogen peroxide/DMSO/Fe++ salt system took place at α-quinolinyl position and led to the respective mono- and dialkyl derivatives 1b-e, 2b-e, 3b,c, and 4b,c. Action of sodium methoxide towards isopropyl derivatives 1b,c and 2b,c caused the 1,4-dithiin ring

  3,4-喹啉二基双硫化物1a，2a，3a和4a的硫酸氢与由烷基碘化物/过氧化氢/ DMSO / Fe ++盐体系形成的异丙基和环己基反应在α-喹啉基位置发生并引发分别对应于单和二烷基衍生物1b-e，2b-e，3b，c和4b，c。甲醇钠对异丙基衍生物1b，c和2b，c的作用导致1,4-二硫辛开环形成（在S-甲基化后）3,4'-和3,3'-二喹啉基硫化物6a，b和3,4'-的衍生物。7a，b。
• α,ω-Bis(4-substituted-3-quinolinylthio)alkanes from reactions of thioquinanthrene with alkoxides
  作者：Stanislaw Boryczka

  DOI：10.1002/jhet.5570350641

  日期：1998.11

  The reaction of thioquinanthrene 1 with sodium alkoxides and α,ω-dihaloalkanes leads to the formation of α,ω-bis[4-(4-methoxy-3-quinolinylthio)-3-quinolinylthio]alkanes 4. The yield depends on the nature of α,ω-dihalo-alkanes. The effect of α,ω-dihaloalkanes of the following types: XCH2X (X = Cl,Br,I), X(CH2)2X (X = Cl,Br,I), Br(CH2)3Br and Br(CH2)6Br were studied. The preparation of 4-alkoxy-3′-(ω-bromoalkylthio)-3

  thioquinanthrene的反应1用醇钠和α，ω-二卤代烷烃导致α，ω -双[4-（4-甲氧基-3- quinolinylthio）-3- quinolinylthio]烷烃的形成4。产率取决于α，ω-二卤代烷烃的性质。下列类型的α，ω-二卤代烷烃的作用：XCH 2 X（X = Cl，Br，I），X（CH 2）2 X（X = Cl，Br，I），Br（CH 2）3 Br研究了Br（CH 2）6 Br。还研究了4-烷氧基-3'-（ω-溴代烷硫基）-3,4'-二喹啉基硫化物3的制备及其向α，ω-双（4-烷氧基-3-喹啉基硫基）烷烃6的转化。
• Reactions of 4-dimethylamino-3-quinolinyl sulfides with nitrating mixture and transamination of 4-dimethylamino-3-methylsulfinyl-6-nitroquinoline
  作者：Elwira Chrobak、Andrzej Maślankiewicz

  DOI：10.1002/jhet.5570450436

  日期：2008.7

  4-Amino-3-quinolinyl sulfides 4d-e and 7a-c were prepared by amination of 4-chloro-3-quinolinyl sulfides 4c or 1c, respectively, in methanol (140-160 °C) or in boiling phenol with yields up to 95 %. Reaction of 4-dimethylamino-3-quinolinyl sulfides 7c and 4e with nitrating mixture proceeded simultanously as oxidation of the methylthio group to the methylsulfinyl one and as C6-nitration to form 6-nitro-β-quinolinyl

  4-氨基-3-喹啉基硫化物4d-e和7a-c是通过在甲醇（140-160°C）或沸腾的苯酚中分别将4-氯-3-喹啉基硫化物4c或1c胺化而制备的，收率最高至95％。4-二甲基氨基-3-喹啉基硫化物7c和4e与硝化混合物的反应同时进行，其中甲硫基氧化为甲基亚磺酰基1，并且C 6硝化分别形成6-硝基-β-喹啉基亚砜9c或10b。当与伯脂族胺和氨反应时，4-二甲基氨基-3-甲基亚磺酰基-6-硝基喹啉9c经历了酸催化的氨基转移反应。