5,5″-dicyano-2,2′:5′,2″-terthiophene | 134273-55-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5″-dicyano-2,2′:5′,2″-terthiophene
• 英文别名: [2,2’:5′,2''-terthiophene]-5,5''-dicarbonitrile；2,2':5',2"-terthiophene-5,5"-dicarbonitrile；5,5''-dicyano-2,2':5',2''-terthiophene；5,5''-dicyanoterthiophene；5,5"-Dicyano-2,2':5',2"-Terthienyl；5-[5-(5-cyanothiophen-2-yl)thiophen-2-yl]thiophene-2-carbonitrile
• CAS: 134273-55-5
• 化学式: C₁₄H₆N₂S₃
• 分子量: 298.413
• InChiKey: ZUECXOWARJNKRK-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212 °C(Solv: hexane (110-54-3); toluene (108-88-3))
• 沸点：
  476.7±45.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,5″-dicyano-2,2′:5′,2″-terthiophene 在 氯化亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 N,N'-distearyl-5,5''-dicyano-2,2':5',2''-terthiophene-4,4''-dicarboxamide
  参考文献：
  名称：

  Synthesis and Mesogenic Properties of Novel Terthiophene Derivatives

  摘要：

  To develop novel oligothiophene-based liquid crystals involving hydrogen bonding, new terthiophene derivatives containing a stearylamide group, N,N'-distearyl-5,5"-dicyano-2,2':5',2"-terthiophene-4,4"-dicarboxamide (DNC18DCN 3T) and N,N'-distearyl-5,5'-dipropyl-2,2': 5',2'-terthiophene-4,4"-dicarboxamide (DNC18 DP3T), were designed and synthesized, and their thermal behavior examined. Although DNC(18)DP3T did not exhibit liquid crystallinity, DNC(18)DCN3T was found to form smectic A phase.

  DOI：

  10.1080/00397910500446290
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 alpha-三联噻吩 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以43%的产率得到5,5″-dicyano-2,2′:5′,2″-terthiophene
  参考文献：
  名称：

  Synthesis and Mesogenic Properties of Novel Terthiophene Derivatives

  摘要：

  To develop novel oligothiophene-based liquid crystals involving hydrogen bonding, new terthiophene derivatives containing a stearylamide group, N,N'-distearyl-5,5"-dicyano-2,2':5',2"-terthiophene-4,4"-dicarboxamide (DNC18DCN 3T) and N,N'-distearyl-5,5'-dipropyl-2,2': 5',2'-terthiophene-4,4"-dicarboxamide (DNC18 DP3T), were designed and synthesized, and their thermal behavior examined. Although DNC(18)DP3T did not exhibit liquid crystallinity, DNC(18)DCN3T was found to form smectic A phase.

  DOI：

  10.1080/00397910500446290

文献信息

• Original synthesis and spectroscopic study of thiophene triazine derivatives with enhanced luminescence properties
  作者：Alysson Duarte Rodrigues、Nathalie Marcotte、Françoise Quignard、Stefano Deabate、Mike Robitzer、Dan A. Lerner

  DOI：10.1016/j.saa.2019.117708

  日期：2020.2

  A straightforward access to π-conjugated oligothiophenes bearing amino-rich groups was developed. Palladium-catalyzed C-H arylation applied in the main step of the synthesis allowed to couple 2-thiophenecarbonitriles and aryl bromides with moderate to excellent yields (35-93%). Then, to improve their basic fluorescence properties, these compounds were transformed into their 2,4-diamino-1,3,5-triazine

  开发了直接进入带有富含氨基的基团的π-共轭低聚噻吩的方法。在合成的主要步骤中应用钯催化的CH芳基化反应，可以中等至极好的收率（35-93％）偶联2-噻吩甲腈和芳基溴化物。然后，为了改善其基本荧光性质，将这些化合物转化为它们的2,4-二氨基-1,3,5-三嗪衍生物，并具有良好或优异的收率（74-98％）。紫外可见吸收和荧光研究确定了一种强发射分子（荧光量子产率：ΦF= 0.78±0.05），该分子可用于生物学和材料化学领域的传感器。我们观察到带有2,4-二氨基-1,3,5-三嗪的低聚噻吩的光谱性质具有拮抗作用，
• Phototoxic compounds for use as insect control agents
  申请人：Her Majesty the Queen in right of Canada, as represented by Minister of

  公开号：US05045563A1

  公开（公告）日：1991-09-03

  A method is provided herein for controlling insects which are harmful to agriculture and forestry and which are also harmful both to humans and to domestic animals. The method involves the steps of applying to a locus infested with such insects, a composition comprising a carrier and a biocidal-amount of a specifically-recited phototoxic, naturally-occurring thiophene, acetylene, or a synthetic, structurally-related derivative, analogue or acetylenic compound. Then, that composition, while at that locus, is subjected to UV radiation in the range of about 300 nm to about 400 nm, for a sufficient time to impart, to such phototoxic naturally-occurring thiophene, acetylene, or synthetic structurally-related derivative, analogue or acetylenic compound the desired insect control activity. Certain of these phototoxic naturally-occurring thiophenes, or acetylenes or synthetic, structurally-related compounds are also novel and provide novel insect control compositions.

  本文提供了一种对农林业有害、对人类和家畜也有害的昆虫进行控制的方法。该方法包括以下步骤：将含有载体和特定的光毒性天然噻吩、乙炔或合成结构相关衍生物、类似物或炔化合物的生物杀灭剂量的组合物应用于受到这些昆虫侵袭的场所。然后，在该场所，将该组合物暴露于300nm至400nm范围内的紫外辐射下，足够长的时间以赋予这些光毒性天然噻吩、乙炔或合成结构相关衍生物、类似物或炔化合物所需的昆虫控制活性。其中一些光毒性天然噻吩、乙炔或合成结构相关化合物也是新颖的，并提供了新颖的昆虫控制组合物。
• Drug delivery system for hydrophobic drugs
  申请人：QLT, Inc.

  公开号：EP1900357A2

  公开（公告）日：2008-03-19

  Compositions comprising microaggregates containing hydrophobic drugs, as well as methods for their production, are described. Such microaggregates may include micelle structures or combinations thereof with liposomes, and constitute an effective delivery vehicle for a hydrophobic agent. Methods for microaggregate production include the use of preferred lipid compounds and processing conditions favoring the production of small aggregates for improved filter sterilization.

  本文介绍了由含有疏水性药物的微团聚体组成的组合物及其生产方法。这种微团聚体可包括胶束结构或其与脂质体的组合，并构成疏水性药物的有效递送载体。微团聚体的生产方法包括使用优选的脂质化合物和有利于生产小团聚体的加工条件，以提高过滤灭菌效果。
• Immuno-adjuvant PDT treatment of metastatic tumors
  申请人：——

  公开号：US20020022032A1

  公开（公告）日：2002-02-21

  Immuno-adjuvant photodynamic therapy to treat and prevent metastatic cancer is effected using photosensitizers in combination with immuno-adjuvants to destroy metastatic tumor cells.

  治疗和预防转移性癌症的免疫辅助光动力疗法是利用光敏剂与免疫辅助剂相结合来破坏转移性肿瘤细胞。
• Supports for photosensitizer formulations
  申请人：——

  公开号：US20020061330A1

  公开（公告）日：2002-05-23

  The invention is generally related to the field of formulating medicaments in association with a solid support. Such formulations comprising photosensitizers, and their use in photodynamic therapy, are also provided. Methods for the production of the medicament formulations are also disclosed.

  本发明一般涉及与固体支持物结合的药物制剂领域。本发明还提供了包含光敏剂的此类制剂及其在光动力疗法中的应用。本发明还公开了药物制剂的生产方法。