3,3'-diiodo-2,2'-bibenzo[b]thiophene | 1181678-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3,3'-diiodo-2,2'-bibenzo[b]thiophene
• 英文别名: 3,3'-diiodo-2,2'-bibenzothiophene；3,3'-diiodo-2,2'-dibenzothiophene；3-Iodo-2-(3-iodo-1-benzothiophen-2-yl)-1-benzothiophene
• CAS: 1181678-15-8
• 化学式: C₁₆H₈I₂S₂
• 分子量: 518.181
• InChiKey: RAVYXVONWFYCPO-UHFFFAOYSA-N

物化性质

• 熔点：
  215-217 °C(Solvent: Hexane ; Ethyl acetate)
• 沸点：
  576.3±50.0 °C(Predicted)
• 密度：
  2.105±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tin 、 3,3'-diiodo-2,2'-bibenzo[b]thiophene 在 碘 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以88%的产率得到
  参考文献：
  名称：

  一种锡芴类化合物的制备方法

  摘要：

  本发明涉及有机半导体材料制备领域，为解决目前合成锡芴类化合物的方法中存在反应条件要求苛刻，反应操作困难，重现性较差等问题，本发明提出了一种锡芴类化合物的制备方法，在惰性气体保护下，向反应器中加入二卤烷烃，锡粉，催化剂、有机溶剂，100℃~160℃下反应12~15h，冷却至室温，萃取、收集有机相、干燥，得到粗产物，然后经处理可得到锡芴类化合物。本发明反应条件易实现，操作简单，纯化步骤，降低成本，而且合成锡芴类化合物可作为反应物继续反应成为链状或环状大分子化合物。

  公开号：

  CN109384810B
• 作为产物：
  描述：

  1-乙炔基-2-(甲硫基)苯 在 吡啶 、 碘 、 copper(II) acetate monohydrate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 9.0h， 生成 3,3'-diiodo-2,2'-bibenzo[b]thiophene
  参考文献：
  名称：

  Linear and Angular Heteroacenes from Double-Electrophilic Cyclization (DEC) and DEC-Reductive Elimination of Diynes

  摘要：

  Linear and angular heteroacenes are prepared from terminal alkynes bearing tethered nucleophiles in two steps. Linear heteroacenes are formed from the homocoupling of these alkynes followed by reaction with a double electrophile (ECl2) to induce a tricyclization reaction cascade involving double-electrophilic cyclization (DEC). Related angular heteroacenes are formed from the prior substitution of the chloro groups in ECl2 with the same terminal alkyne followed by reaction with AuCl3 to produce a DEC-reductive-elimination (DECRE) reaction.

  DOI：

  10.1021/acs.orglett.7b00265

文献信息

• Iodine/Palladium Approaches to the Synthesis of Polyheterocyclic Compounds
  作者：Saurabh Mehta、Richard C. Larock

  DOI：10.1021/jo902639f

  日期：2010.3.5

  A simple, straightforward strategy for the synthesis of polyheterocyclic compounds (PHCs) is reported, which involves iterative cycles of palladium-catalyzed Sonogashira coupling, followed by iodocyclization using I2 or ICl. A variety of heterocyclic units, including benzofurans, benzothiophenes, indoles, and isocoumarins, can be efficiently incorporated under mild reaction conditions. In addition

  报道了一种简单、直接的合成多杂环化合物 (PHC) 的策略，该策略涉及钯催化的 Sonogashira 偶联的迭代循环，然后使用 I 2或 ICl进行碘环化。多种杂环单元，包括苯并呋喃、苯并噻吩、吲哚和异香豆素，可以在温和的反应条件下有效地结合。此外，这种策略的变体提供了各种连接和融合的 PHC。
• Annulative π-extension of indoles and pyrroles with diiodobiaryls by Pd catalysis: rapid synthesis of nitrogen-containing polycyclic aromatic compounds
  作者：Hiroyuki Kitano、Wataru Matsuoka、Hideto Ito、Kenichiro Itami

  DOI：10.1039/c8sc02802h

  日期：——

  A palladium-catalyzed one-step annulative π-extension (APEX) reaction of indoles and pyrroles that allows rapid access to nitrogen-containing polycyclic aromatic compounds is described. In the presence of palladium pivalate and silver carbonate, diverse indoles or pyrroles coupled with diiodobiaryls in a double direct C–H arylation manner to be transformed into the corresponding π-extended compounds

  描述了一种钯催化的吲哚和吡咯的一步环π延伸（APEX）反应，该反应允许快速获得含氮多环芳香族化合物。在新戊酸钯和碳酸银存在下，多种吲哚或吡咯与二碘联二芳基以双直接C-H芳基化方式偶联，一步转化为相应的π-延伸化合物。新开发的催化系统能够使用各种吡咯和吲哚作为模板与一系列二碘联芳基化合物，以提供结构复杂且大量π延伸的含氮多环芳香族化合物，否则这些化合物很难合成。
• FUSED RING COMPOUND, METHOD FOR PRODUCING THE SAME, POLYMER, ORGANIC THIN FILM CONTAINING THE COMPOUND AND/OR THE POLYMER, AND ORGANIC THIN FILM DEVICE AND ORGANIC THIN FILM TRANSISTOR EACH COMPRISING THE ORGANIC THIN FILM
  申请人：Osaka University

  公开号：EP2251342A1

  公开（公告）日：2010-11-17

  An object of the present invention is to provide a fused ring compound which can show sufficient charge transport properties and also has excellent solubility in a solvent. The fused ring compound of the present invention is represented by the following formula (1): wherein R11 and R12 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylamino group, an alkoxycarbonyl group having 3 or more carbon atoms in the alkyl moiety thereof, an aryl group which may have a substituent, a monovalent heterocyclic group which may have a substituent, or a cyano group, wherein at least one of R11 and R12 is not a hydrogen atom; R13 and R14 each independently represent a monovalent group and m and n are an integer of 0 to 2; Y11, Y12, Y13 and Y14 are a predetermined divalent group containing S, O, N, Se, Te or a double bond; Y11 and Y12 are selected so that a ring containing the groups forms a five-membered ring; and Y13 and Y14 are selected so that a ring containing the groups forms a five or six-membered ring.

  本发明的目的是提供一种融合环化合物，它能显示出足够的电荷传输特性，并且在溶剂中具有极佳的溶解性。本发明的熔环化合物由下式（1）表示： 其中 R11 和 R12 各自独立地代表氢原子、烷基、烷氧基、烷硫基、烷氨基、在其烷基中具有 3 个或更多碳原子的烷氧羰基、可具有取代基的芳基、可具有取代基的单价杂环基团或氰基，其中 R11 和 R12 中至少有一个不是氢原子；R13和R14各自独立地代表一个一价基团，m和n是0至2的整数；Y11、Y12、Y13和Y14是含有S、O、N、Se、Te或双键的预定二价基团；Y11和Y12的选择使含有这些基团的环形成一个五元环；Y13和Y14的选择使含有这些基团的环形成一个五元或六元环。
• EP2251342
  申请人：——

  公开号：——

  公开（公告）日：——
• FUSED RING COMPOUND, METHOD FOR PRODUCING THE SAME, POLYMER, ORGANIC THIN FILM CONTAINING THE COMPOUND AND/OR POLYMER, AND ORGANIC THIN FILM DEVICE AND ORGANIC THIN FILM TRANSISTOR EACH COMPRISING THE ORGANIC THIN FILM
  申请人：Miura Masahiro

  公开号：US20110065895A1

  公开（公告）日：2011-03-17

  An object of the present invention is to provide a fused ring compound which can show sufficient charge transport properties and also has excellent solubility in a solvent. The fused ring compound of the present invention is represented by the following formula (1): wherein R 11 and R 12 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylamino group, an alkoxycarbonyl group having 3 or more carbon atoms in the alkyl moiety thereof, an aryl group which may have a substituent, a monovalent heterocyclic group which may have a substituent, or a cyano group, wherein at least one of R 11 and R 12 is not a hydrogen atom; R 13 and R 14 each independently represent a monovalent group and m and n are an integer of 0 to 2; Y 11 , Y 12 , Y 13 and Y 14 are a predetermined divalent group containing S, O, N, Se, Te or a double bond; Y 11 and Y 12 are selected so that a ring containing the groups forms a five-membered ring; and Y 13 and Y 14 are selected so that a ring containing the groups forms a five or six-membered ring.