1,2-dihydro-9-chloro-1,10-phenanthroline-2-thion | 144224-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 1,2-dihydro-9-chloro-1,10-phenanthroline-2-thion
• 英文别名: 9-chloro-1,10-phenantroline-2(1H)-thione；9-chloro-1,10-phenanthroline-2(1H)-thione；9-Chloro-1,10-phenanthroline-2(1H)-thione；9-chloro-1H-1,10-phenanthroline-2-thione
• CAS: 144224-14-6
• 化学式: C₁₂H₇ClN₂S
• 分子量: 246.72
• InChiKey: BUSQXDUHXUSOEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-9-chloro-1,10-phenanthroline-2-thion 以 二苯醚 为溶剂， 反应 4.0h， 以62%的产率得到2,2'-thiobis(1,10-phenanthroline)
  参考文献：
  名称：

  Displacement reactions of 2-chloro- and 2,9-dichloro-1,10-phenanthroline: synthesis of a sulfur-bridged bis-1,10-phenanthroline macrocycle and a 2,2′-amino-substituted-bis-1,10-phenanthroline

  摘要：

  The synthesis and structural assignments of 9-chloro-1,1-phenanthroline-2(1H)-thione and 1,10-dihydro-1,10-phenanthroline-2,9-dithione have been accomplished. The sulfur-bridged bis-1,10-phenanthroline macrocycle was readily prepared by heating the thione or equimolar amounts of the dithione and 2,9-dichloro-1,10-phenanthroline in diphenyl ether. Displacements of 2-chloro- or 2,9-dichloro-1,10-phenanthroline with N,N-dimethylethylenediamine afforded the corresponding airline and diamino analogues. Am amino-substituted-2,2'-bis-1,10-phenanthroline has been prepared. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.138
• 作为产物：
  描述：

  2,9-二氯-1,10-菲罗啉 在 硫脲 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以34%的产率得到1,2-dihydro-9-chloro-1,10-phenanthroline-2-thion
  参考文献：
  名称：

  Displacement reactions of 2-chloro- and 2,9-dichloro-1,10-phenanthroline: synthesis of a sulfur-bridged bis-1,10-phenanthroline macrocycle and a 2,2′-amino-substituted-bis-1,10-phenanthroline

  摘要：

  The synthesis and structural assignments of 9-chloro-1,1-phenanthroline-2(1H)-thione and 1,10-dihydro-1,10-phenanthroline-2,9-dithione have been accomplished. The sulfur-bridged bis-1,10-phenanthroline macrocycle was readily prepared by heating the thione or equimolar amounts of the dithione and 2,9-dichloro-1,10-phenanthroline in diphenyl ether. Displacements of 2-chloro- or 2,9-dichloro-1,10-phenanthroline with N,N-dimethylethylenediamine afforded the corresponding airline and diamino analogues. Am amino-substituted-2,2'-bis-1,10-phenanthroline has been prepared. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.138

文献信息

• Synthesis and DNA Cleaving Activity of Copper-complex of Macrocyclic Compound Containing 1,10-Phenanthroline
  作者：Miwa Hirai、Kazuo Shinozuka、Hiroaki Sawai、Shojiro Ogawa

  DOI：10.1246/cl.1992.2023

  日期：1992.10

  Copper-complexes of 1,14: 7,8-diethenotetrapyrido-[2,1,6-de: 2′,1′,6′-gh: 2″, 1″, 6″-kl: 2″′,1″′, 6″′-na][1,5,8,12] tetraaza-[3,10] dithiocyclotetradecine (SMC) consisting of two 1,10-phenanthroline molecules bridged by sulfur, was synthesized. Interaction of Cu-SMC with DNA was examined by spectroscopic methods. Cu-SMC binds with DNA and cleaves DNA in the presence of a reducing agent under an aerobic

  1,14 的铜配合物：7,8-二烯四吡啶-[2,1,6-de: 2',1',6'-gh: 2", 1", 6"-kl: 2"',1合成了“', 6”'-na][1,5,8,12] 四氮杂-[3,10] 二硫代环十四烷 (SMC)，由两个由硫桥接的 1,10-菲咯啉分子组成。通过光谱方法检查 Cu-SMC 与 DNA 的相互作用。Cu-SMC 在有氧条件下，在还原剂存在的情况下与 DNA 结合并切割 DNA。
• Synthesis of a New Copper Complex of a Macrocyclic Compound Consisting of 1,10-Phenanthroline, and Its DNA Binding and Cleaving Activity
  作者：Miwa Hirai、Kazuo Shinozuka、Hiroaki Sawai、Shojiro Ogawa

  DOI：10.1246/bcsj.67.1147

  日期：1994.4

  interaction of [Cu(smc)] with DNA was examined by UV-vis absorption spectroscopy, circular dichroism spectroscopy, and viscometry. The binding constant of [CuI(smc)] with DNA is 4.2 × 104 M−1, which is almost identical with that of bis(1,10-phenanthroline)copper, [CuI(phen)2]. A viscosity measurement indicates that [CuI(smc)] binds to DNA by an intercalative mode. [Cu(smc)] cleaves DNA in the presence of a

  合成了由两个硫原子 [Cu(smc)] 桥接的两个 1,10-菲咯啉分子组成的大环化合物的铜配合物。[Cu(smc)] 与 DNA 的相互作用通过 UV-vis 吸收光谱、圆二色光谱和粘度测定法进行了检查。[CuI(smc)]与DNA的结合常数为4.2 × 104 M-1，与双(1,10-菲咯啉)铜[CuI(phen)2]的结合常数几乎相同。粘度测量表明 [CuI(smc)] 通过嵌入模式与 DNA 结合。[Cu(smc)] 在有氧条件下，在还原剂存在的情况下切割 DNA。在这个过程中·OH起着重要的作用。
• Displacement reactions of 2-chloro- and 2,9-dichloro-1,10-phenanthroline: synthesis of a sulfur-bridged bis-1,10-phenanthroline macrocycle and a 2,2′-amino-substituted-bis-1,10-phenanthroline
  作者：A. Paul Krapcho、Silvia Sparapani、Amber Leenstra、Joshua D. Seitz

  DOI：10.1016/j.tetlet.2009.01.138

  日期：2009.7

  The synthesis and structural assignments of 9-chloro-1,1-phenanthroline-2(1H)-thione and 1,10-dihydro-1,10-phenanthroline-2,9-dithione have been accomplished. The sulfur-bridged bis-1,10-phenanthroline macrocycle was readily prepared by heating the thione or equimolar amounts of the dithione and 2,9-dichloro-1,10-phenanthroline in diphenyl ether. Displacements of 2-chloro- or 2,9-dichloro-1,10-phenanthroline with N,N-dimethylethylenediamine afforded the corresponding airline and diamino analogues. Am amino-substituted-2,2'-bis-1,10-phenanthroline has been prepared. (C) 2009 Elsevier Ltd. All rights reserved.