3,4-ethylenedioxythiophene- 2,5-dicarbonyl chloride | 388602-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3,4-ethylenedioxythiophene- 2,5-dicarbonyl chloride
• 英文别名: 3,4-Ethylenedioxythiophene-2,5-dicarbonyl chloride；2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbonyl chloride
• CAS: 388602-24-2
• 化学式: C₈H₄Cl₂O₄S
• 分子量: 267.089
• InChiKey: VDMWUKUZYBREJW-UHFFFAOYSA-N

物化性质

• 沸点：
  425.5±45.0 °C(Predicted)
• 密度：
  1.662±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-ethylenedioxythiophene- 2,5-dicarbonyl chloride 在 氯化亚砜 、 氨 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 为溶剂， 反应 209.0h， 生成 2,5-bis(N-phenylamidino)-3,4-ethylenedioxythiophene
  参考文献：
  名称：

  3,4-乙撑二氧噻吩连接的新型芳族二am的合成，DNA / RNA亲和力和抗肿瘤活性

  摘要：

  合成了一系列新颖的2,5-双（（基苯基）-3,4-亚乙基二氧噻吩（5 – 10和15）。化合物5 – 10作为主要的结合位点与DNA小沟结合，并强烈稳定ct-DNA的双螺旋。出乎意料的是，相同的化合物还可以使ds-RNA热稳定，从而使它们中的大多数沿着RNA双螺旋形成堆积的二聚体。唯一的例外是化合物15，由于其结构特点，它与DNA或RNA没有相互作用。化合物5 – 10具有中等至强的细胞毒性作用（GI 50 = 1.5–9.0μM），由七个肿瘤细胞系组成。由于二咪唑啉衍生物9对所有受试肿瘤细胞系的生长具有最高的抑制潜力，因此通过测试其进入细胞并影响细胞周期的能力，对其进行了更详细的研究。在30分钟的孵育时间内，化合物9（5μM）已成功内化到细胞质中，随后在90分钟的孵育中进行了核定位。在等毒性（50μM）浓度下的细胞周期分析显示，HeLa细胞在G2 / M期明显停滞，表明所研究的化合物与细

  DOI：

  10.1016/j.ejmech.2010.12.010
• 作为产物：
  描述：

  3,4-乙撑二氧基噻吩-2,5-二羧酸 在 N,N-二甲基甲酰胺 氯化亚砜 作用下， 以78%的产率得到3,4-ethylenedioxythiophene- 2,5-dicarbonyl chloride
  参考文献：
  名称：

  Synthetic routes to bis(pyrrolyl)arylenes. Experimental and molecular modeling studies

  摘要：

  描述了从9,9-二烷基芴和1,4-二氧杂[3,4-b]噻吩衍生的化合物的合成与表征。关键步骤涉及9,9-二烷基-2,7-N,N′-二烯基亚氯芴或2,5-N,N′-二烯基亚氯乙烯二氧噻吩与叔丁基氢氧化钾之间的改进Steglich反应（路线1）。路线2针对双（吡咯-2-基）二氧杂噻吩，涉及1,4-二氧杂[2,3-c]噻吩与二氧杂环丙醇的反应，也是一种有效且通用的策略。分子模拟研究表明，合成部分的分子参数（结构、离子化势、原子电荷）与其聚合特性之间存在关系。

  DOI：

  10.1039/b101731o

文献信息

• [EN] AMIDE-BASED HOLE-TRANSPORTING OR HOLE-INJECTING MATERIALS<br/>[FR] MATÉRIAUX DE TRANSPORT DE TROUS OU D'INJECTION DE TROUS À BASE D'AMIDE
  申请人：UNIV MUENCHEN LUDWIG MAXIMILIANS

  公开号：WO2018019774A1

  公开（公告）日：2018-02-01

  The present invention provides a hole-transporting or hole-injecting material for an optoelectronic device, comprising a compound of the formula (I) and/or a compound of the formula (II), (I) (II) wherein: Ar1 and Ar2 independently represent an optionally substituted arylene group, an optionally substituted heteroarylene group or an optionally substituted fluorenylene group; R1 and R2 independently represent hydrogen or a group -NAr6Ar7, wherein Ar6 and Ar7 are independently an optionally substituted aryl group, an optionally substituted heteroaryl group, or an optionally substituted fluorenylene group, and wherein a direct covalent bond may be present between Ar6 and Ar7 such that a fused heterocyclic ring system is formed which contains Ar6, Ar7 and the nitrogen atom to which they are attached; L1 and L3 independently represent a bond, an optionally substituted arylene group, an optionally substituted fluorenylene group, or an optionally substituted heteroarylene group; and L2 represents a bond, an optionally substituted arylene group, an optionally substituted heteroarylene group, an optionally substituted fluorenylene group, or a group - Ar3-N(Ar4)-Ar5-, wherein Ar3 and Ar5 represent optionally substituted arylene groups, and Ar4 represents an optionally substituted aryl group.

  本发明提供了一种用于光电子器件的传输孔或注入孔的材料，包括符合式(I)的化合物和/或符合式(II)的化合物，其中：Ar1和Ar2分别代表可选择取代的芳基、可选择取代的杂芳基或可选择取代的芬啶基；R1和R2分别代表氢或基团-NAr6Ar7，其中Ar6和Ar7分别代表可选择取代的芳基、可选择取代的杂芳基或可选择取代的芬啶基，并且Ar6和Ar7之间可能存在直接共价键，形成包含Ar6、Ar7和它们附着的氮原子的融合杂环系统；L1和L3分别代表键、可选择取代的芳基、可选择取代的芬啶基或可选择取代的杂芳基；L2代表键、可选择取代的芳基、可选择取代的杂芳基、可选择取代的芬啶基或基团-Ar3-N(Ar4)-Ar5-，其中Ar3和Ar5代表可选择取代的芳基，Ar4代表可选择取代的芳基。
• Design and Synthesis of New Amides and Thioamides Derived from 3,4-Ethylenedioxythiophene as Potential Anticonvulsants
  作者：Ravi Kulandasamy、Airody Vasudeva Adhikari、James P. Stables

  DOI：10.5012/bkcs.2010.31.11.3318

  日期：2010.11.20

  Five new series of 3,4-ethylenedioxythiophene derivatives carrying important pharamacophores, viz., amide, ester, ether and active secondary aryl moieties have been designed and synthesized through multistep reactions starting from thiodiglycolic ester and diethyl oxalate. They have been characterized by elemental and spectral data. All the target compounds have been screened for their anticonvulsant

  通过从硫代二甘醇酯和草酸二乙酯开始的多步反应，设计并合成了五个新系列的 3,4-乙烯二氧噻吩衍生物，这些衍生物带有重要的药物载体，即酰胺、酯、醚和活性仲芳基部分。它们的特征是元素和光谱数据。所有目标化合物都在三种不同的模型中进行了抗惊厥活性筛选，即。最大电击 (MES)、皮下甲唑 (scMET) 和 6 Hz 筛选并评估它们在转子模型中的神经毒性。化合物 6a 以铅的形式出现，没有神经毒性。所有五个系列的化合物在毒性研究中都是安全的，最大剂量为 300 mg/kg 体重。在测试的化合物中，
• Axial chirality of N,N′-disubstituted 3,4-ethylenedioxythiophene-2,5-dicarboxamides
  作者：Ivana Stolić、Krešimir Molčanov、Goran Kovačević、Biserka Kojić-Prodić、Miroslav Bajić

  DOI：10.1007/s11224-011-9885-x

  日期：2012.4

  A series of N,N’-disubstituted 3,4-ethylenedioxythiophene-2,5-dicarboxamides was synthesised by amide bond formation between 3,4-ethylenedioxythiophene-2,5-dicarbonyl chloride and corresponding primary amines, where the size and the nature of the substituent were varied. The crystal structures of prepared compounds were determined by X-ray structure analysis. Mechanism and reaction rates of interconversion between conformational isomers were obtained by DFT calculations. All studied compounds reveal axial chirality with molecular symmetry C 2. Amide bond isomerisation and twisting of the dioxane ring in studied compounds results in the formation of series of conformers of which the s-trans/s-trans conformer is energetically most favourable.

  通过3,4-乙撑二氧噻吩-2,5-二甲酰氯与相应的伯胺之间形成酰胺键合成了一系列N,N'-二取代的3,4-乙撑二氧噻吩-2,5-二甲酰胺，其中尺寸和性质取代基不同。通过X射线结构分析确定了所制备化合物的晶体结构。通过DFT计算得到了构象异构体之间相互转化的机理和反应速率。所有研究的化合物都显示出具有分子对称性 C 2 的轴向手性。研究的化合物中酰胺键异构化和二恶烷环的扭曲导致形成一系列构象异构体，其中 s-trans/s-trans 构象异构体在能量上最有利。
• AMIDE-BASED HOLE-TRANSPORTING OR HOLE-INJECTING MATERIALS
  申请人：Ludwig-Maximilians-Universität München

  公开号：EP3275865A1

  公开（公告）日：2018-01-31

  The present invention provides a hole-transporting or hole-injecting material for an optoelectronic device, comprising a compound of the formula (I) and/or a compound of the formula (II) wherein: Ar1 and Ar2 independently represent an optionally substituted arylene group, an optionally substituted heteroarylene group or an optionally substituted fluorenylene group; R1 and R2 independently represent hydrogen or a group -NAr6Ar7, wherein Ar6 and Ar7 are independently an optionally substituted aryl group, an optionally substituted heteroaryl group, or an optionally substituted fluorenylene group, and wherein a direct covalent bond may be present between Ar6 and Ar7 such that a fused heterocyclic ring system is formed which contains Ar6, Ar7 and the nitrogen atom to which they are attached; L1 and L3 independently represent a bond, an optionally substituted arylene group, an optionally substituted fluorenylene group, or an optionally substituted heteroarylene group; L2 represents a bond, an optionally substituted arylene group, an optionally substituted heteroarylene group, an optionally substituted fluorenylene group, or a group - Ar3-N(Ar4)-Ar5-, wherein Ar3 and Ar5 represent optionally substituted arylene groups, and Ar4 represents an optionally substituted aryl group; and R3 and R4 independently represent hydrogen, an alkyl group or an aryl group.

  本发明提供了一种用于光电设备的空穴传输或空穴注入材料，该材料由式（I）化合物和/或式（II）化合物组成 其中 Ar1 和 Ar2 独立地代表任选取代的芳基、任选取代的杂芳基或任选取代的芴基； R1 和 R2 独立地代表氢或基团 -NAr6Ar7，其中 Ar6 和 Ar7 独立地代表任选取代的芳基、任选取代的杂芳基或任选取代的芴基，并且 Ar6 和 Ar7 之间可能存在直接共价键，从而形成包含 Ar6、Ar7 及其连接的氮原子的融合杂环系统； L1 和 L3 各自代表键、任选取代的芳烯基、任选取代的芴基或任选取代的杂芳基； L2 代表键、任选取代的芳烯基、任选取代的杂芳基、任选取代的芴基或基团-Ar3-N(Ar4)-Ar5-，其中 Ar3 和 Ar5 代表任选取代的芳烯基，Ar4 代表任选取代的芳基；以及 R3 和 R4 独立地代表氢、烷基或芳基。
• Synthesis, DNA Interactions and Anticancer Evaluation of Novel Diamidine Derivatives of 3,4-Ethylenedioxythiophene
  作者：Ivana Stolić、Monika Avdičević、Nikola Bregović、Ivo Piantanida、Ljubica Glavaš-Obrovac、Miroslav Bajić

  DOI：10.5562/cca2141

  日期：——

  Eight novel diamidino 3,4-ethylenedioxythiophene-2,5-dicarboxanilides (5a-h), obtained by condensation reaction of 3,4-ethylenedioxythiophene-2,5-dicarbonyl chloride and corresponding 3- or 4-aminobenzamidines, were evaluated for interactions with double-stranded DNA and RNA, and their cytotoxicity was assayed against the panel of human cancer cell lines. All compounds preferentially bind into the minor groove of DNA and had higher affinity for DNA than for RNA. Compounds 5a-h showed a moderate antiproliferative effect toward the panel of seven carcinoma cells line, whereby the highest inhibitory potential was displayed by compound 5a with unsubstituted amidino moieties in para position. (doi: 10.5562/cca2141)