2-(3,5-dichlorophenyl)thiophene | 651329-42-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3,5-dichlorophenyl)thiophene
• CAS: 651329-42-9
• 化学式: C₁₀H₆Cl₂S
• 分子量: 229.13
• InChiKey: UOQJFUWRQJNPLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  噻吩 、 3,5-二氯苯胺 在 亚硝酸特丁酯 、 5,15-bis(pentafluorophenyl)-10-(4-cyanophenyl)corrole 作用下， 以 二甲基亚砜 为溶剂， 以58 %的产率得到2-(3,5-dichlorophenyl)thiophene
  参考文献：
  名称：

  阳光诱导芳香杂环的 CH 芳基化：A3 和 A2B 型咔咯作为光氧化还原催化剂的第一个例子

  摘要：

  可见光介导的无金属方法已被开发用于使用苯胺作为起始材料的 C-H 芳基化和硼基化。合成了一系列芳基咔咯（A型和AB型），并在蓝光和阳光下测试了它们的催化潜力。该方法包括取代苯胺作为昂贵的芳基重氮盐的来源，并且在室温下仅使用0.5至1mol%的咔咯催化剂。 Corrole 催化剂在蓝光/阳光下有效地产生杂联芳基化合物和芳基硼​​酸酯，产率相当高（15-80%）。从 TD-DFT 研究中获得了机理见解，表明单电子转移 (SET) 从咔咯催化剂的单线态到芳基重氮盐。该论文展示了基于咔咯的光氧化还原催化作为 C-H 芳基化反应的温和、绿色和生态可持续的替代方案。

  DOI：

  10.1016/j.jcat.2024.115705

文献信息

• PROCESS FOR PRODUCING DENDRIMER, BUILDING BLOCK COMPOUND, AND PROCESS FOR PRODUCING THIOPHENE COMPOUND
  申请人：Toyo Gosei Co., Ltd.

  公开号：EP1535942A1

  公开（公告）日：2005-06-01

  A method for producing a dendrimer having a structural repeating unit which is represented by formula (1) and which contains a linear portion including a thienylene moiety and a branch portion Y formed of an optionally substituted trivalent organic group. The method is based on the convergent method and includes reaction step 1 of converting α-position hydrogen of the thiophene ring of a thienylene-moiety-containing compound (a) for forming end moieties to an active group V1 which undergoes Suzuki cross-coupling reaction, to thereby form compound (b); reaction step 2 of subjecting a compound (c) to Suzuki cross-coupling reaction with the compound (b), to thereby yield compound (d), the compound (c) having a linear portion and a branch portion Y and having, at the branch portion Y, two active groups V2 which undergo Suzuki cross-coupling reaction with the active group V1; reaction step 3 of converting α-position hydrogen of the thiophene ring of the thus-formed compound to an active group V1 which undergoes Suzuki cross-coupling reaction, and reacting the compound (c) with the active group V1, to thereby form a dendron of a subsequent generation; and a step of repeating the reaction step 3 in accordance with needs, to thereby form a dendrimer.

  一种生产树枝状聚合物的方法，该树枝状聚合物具有结构重复单元，其结构重复单元由式（1）表示，包含包括噻吩分子的线性部分和由任选取代的三价有机基团形成的分支部分Y。该方法以聚合法为基础，包括反应步骤 1：将含噻吩基化合物（a）的噻吩环的α位氢转化为活性基团 V1，使其发生铃木交叉偶联反应，从而形成化合物（b）；反应步骤 2：将化合物（c）与化合物（b）进行铃木交叉偶联反应，从而生成化合物（d），化合物（c）具有线性部分和分支部分 Y，并且在分支部分 Y 上具有两个活性基团 V2，这两个活性基团与活性基团 V1 进行铃木交叉偶联反应；反应步骤 3：将由此形成的化合物的噻吩环的α位氢转化为发生铃木交叉偶联反应的活性基团 V1，并使化合物（c）与活性基团 V1 反应，从而形成后续的树枝状化合物；以及根据需要重复反应步骤 3，从而形成树枝状聚合物。
• Process for producing dendrimer, building block compound, and process for producing thiophene compound
  申请人：Obara Satoru

  公开号：US20060122364A1

  公开（公告）日：2006-06-08

  A method for producing a dendrimer having a structural repeating unit which is represented by formula (1) and which contains a linear portion including a thienylene moiety and a branch portion Y formed of an optionally substituted trivalent organic group. The method is based on the convergent method and includes reaction step 1 of converting α-position hydrogen of the thiophene ring of a thienylene-moiety-containing compound (a) for forming end moieties to an active group V 1 which undergoes Suzuki cross-coupling reaction, to thereby form compound (b); reaction step 2 of subjecting a compound (c) to Suzuki cross-coupling reaction with the compound (b), to thereby yield compound (d), the compound (c) having a linear portion and a branch portion Y and having, at the branch portion Y, two active groups V 2 which undergo Suzuki cross-coupling reaction with the active group V 1 ; reaction step 3 of converting α-position hydrogen of the thiophene ring of the thus-formed compound to an active group V 1 which undergoes Suzuki cross-coupling reaction, and reacting the compound (c) with the active group V 1 , to thereby form a dendron of a subsequent generation; and a step of repeating the reaction step 3 in accordance with needs, to thereby form a dendrimer.

  一种生产树枝状聚合物的方法，该树枝状聚合物具有结构重复单元，其结构重复单元由式（1）表示，包含包括噻吩分子的线性部分和由任选取代的三价有机基团形成的分支部分Y。该方法基于聚合法，包括反应步骤 1：将含噻吩基化合物（a）的噻吩环的α位氢转化为活性基团 V，以形成末端分子。 1 反应步骤 2 将化合物 (c) 与化合物 (b) 进行铃木交叉偶联反应，从而得到化合物 (d)，化合物 (c) 具有线性部分和分支部分 Y，并在分支部分 Y 上具有两个活性基团 V 2 与活性基团 V2 发生铃木交叉偶联反应 1 反应步骤 3 将由此形成的化合物中噻吩环的α位氢转化为活性基团 V 1 发生铃木交叉偶联反应，并使化合物 (c) 与活性基团 V 1 与活性基团 V 1 反应，从而形成下一代树枝状化合物；以及根据需要重复反应步骤 3 的步骤，从而形成树枝状聚合物。
• METHOD FOR PRODUCING A ENDRIMER, BUILDING BLOCK COMPOUND, AND METHOD FOR PRODUCING A THIOPHENE COMPOUND
  申请人：Toyo Gosei Co., Ltd.

  公开号：EP1535942B1

  公开（公告）日：2007-04-11
• US7531619B2
  申请人：——

  公开号：US7531619B2

  公开（公告）日：2009-05-12
• Photoredox Catalysis by 21‐Thiaporphyrins: A Green and Efficient Approach for C−N Borylation and C−H Arylation
  作者：Anu Janaagal、Apoorv Kushwaha、Pranjali Jhaldiyal、T. J. Dhilip Kumar、Iti Gupta

  DOI：10.1002/chem.202401623

  日期：2024.8.19

  The photocatalytic C‐N borylation and C‐H arylation mostly depend on the ruthenium and iridium complexes or eosin Y and the use of porphyrin catalysts is still in infancy. A series of novel 21‐thiaporphyrins (A2B2 and A3B type) were synthesized having carbazole/phenothiazine moieties at their meso‐positions and screened as catalysts for C‐N borylation and C‐H arylation. This paper demonstrates the 21‐thiaporphyrin catalyzed C‐N borylation and het‐arylation of anilines under visible light. The method utilizes only 0.1 mol% of 21‐thiaporphyrin catalyst under blue light for the direct C‐N borylation and het‐arylation reactions. A variety of substituted anilines were used as source for expensive and unstable aryl diazonium salts in the reactions. The heterobiaryls and aryl boronic esters were obtained in decent yields (up to 88%). Versatility of the 21‐thiaporphyrin catalyst was tested by thiolation and selenylation of anilines under similar conditions. Mechanistic insight was obtained from DFT studies, suggesting that 21‐thiaporphyrin undergo an oxidative quenching pathway. The photoredox process catalyzed by 21‐thiaporphyrins offers a mild, efficient and metal‐free alternative for the formation of C‐C, C‐S, and C‐Se bonds in aryl compounds; it can also be extended to borylation reaction.