3-([1,1'-biphenyl]-4-yl)benzo[b]thiophene

• 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: 3-([1,1'-biphenyl]-4-yl)benzo[b]thiophene
• 英文别名: 3-(4-Phenylphenyl)-1-benzothiophene
• 化学式: C₂₀H₁₄S
• 分子量: 286.397
• InChiKey: BTEBNHLWTVYEQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• 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

• 作为反应物：
  描述：

  3-([1,1'-biphenyl]-4-yl)benzo[b]thiophene 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 以85 %的产率得到2-([1,1'-biphenyl]-4-yl)benzo[b]thiophene
  参考文献：
  名称：

  Aryl Dance Reaction of Arylbenzoheteroles

  摘要：

  DOI：

  10.1021/acs.orglett.2c03442
• 作为产物：
  描述：

  4-biphenylboronic acid MIDA ester 、 苯并噻吩 在 三氟甲磺酸 、 C₂₄H₃₆N₂O₂Pd*2C₂H₄O₂ 、 氧化汞红 、 三氟乙酸 、 对苯醌 、 silver(l) oxide 作用下， 以 水 为溶剂， 反应 20.0h， 以65%的产率得到3-([1,1'-biphenyl]-4-yl)benzo[b]thiophene
  参考文献：
  名称：

  Palladium-Catalyzed Phosphine-Free Direct C–H Arylation of Benzothiophenes and Benzofurans Involving MIDA Boronates

  摘要：

  With high regioselectivity, a series of benzoheterocyclic compounds were synthesized via palladiium-catalyzed phosphine-free C-H arylation of benzothiophenes/benzofurans with aryl MIDA boronates at 30-50 degrees C in moderate to excellent yields. MIDA boronates were used in C-H arylation of heterocycles for the first time. Under the optimal conditions, the benzothiophenes could be transformed into the beta-arylbenzothiophenes, and the benzofurans gave only alpha-aryl-substituted products.

  DOI：

  10.1055/s-0034-1379606

文献信息

• Synthesis of [1]Benzothieno[2,3-<i>b</i>][1]benzothiophenes from 3-Arylbenzo[<i>b</i>]thiophenes through Iodine-Mediated Sulfur Insertion Reaction
  作者：Kazuki Ito、Shuta Sakai、Kazuhiro Yoshida

  DOI：10.1021/acs.joc.3c01618

  日期：2023.10.20

  The reaction of 3-arylbenzo[b]thiophenes and elemental sulfur to obtain [1]benzothieno[2,3-b][1]benzothiophenes (BTBTs) is reported. The addition of molecular iodine is essential for the reaction. In previous reactions that used 1,1-diarylethylenes as the starting material, side products that were difficult to separate were generated. The present reaction does not produce such side products and is

  报道了3-芳基苯并[ b ]噻吩与元素硫反应得到[1]苯并噻吩并[2,3- b ][1]苯并噻吩（BTBT）。分子碘的添加对于该反应至关重要。在以前使用1,1-二芳基乙烯作为起始原料的反应中，会产生难以分离的副产物。本反应不产生此类副产物，因此有利于以高收率和纯度获得BTBT。
• SUBSTITUTED CARBOXYLIC ACIDS
  申请人：The Institutes for Pharmaceutical Discovery, LLC

  公开号：EP1620420A2

  公开（公告）日：2006-02-01
• [EN] SUBSTITUTED CARBOXYLIC ACIDS<br/>[FR] ACIDES CARBOXYLIQUES SUBSTITUES
  申请人：INST FOR PHARM DISCOVERY INC

  公开号：WO2004099168A2

  公开（公告）日：2004-11-18

  The present invention relates to compounds and pharmaceutically acceptable salts of formula (I) : which are useful in the treatment of metabolic disorders related to insulin resistance or hyperglycemia. These compounds include inhibitors of protein tyrosine phosphatase (PTP-1B) that are useful in the treatment of diabetes and other PTB-1B mediated diseases, such as cancer, neurodegenerative diseases and the like. The compounds of the invention are also useful in pharmaceutical compositions and methods of treating the aforementioned conditions.
• Palladium-Catalyzed Phosphine-Free Direct C–H Arylation of Benzothiophenes and Benzofurans Involving MIDA Boronates
  作者：Mengmeng Huang、Yangjie Wu、Zhiwei Wang、Yabo Li、Beiqi Yan

  DOI：10.1055/s-0034-1379606

  日期：——

  With high regioselectivity, a series of benzoheterocyclic compounds were synthesized via palladiium-catalyzed phosphine-free C-H arylation of benzothiophenes/benzofurans with aryl MIDA boronates at 30-50 degrees C in moderate to excellent yields. MIDA boronates were used in C-H arylation of heterocycles for the first time. Under the optimal conditions, the benzothiophenes could be transformed into the beta-arylbenzothiophenes, and the benzofurans gave only alpha-aryl-substituted products.
• Aryl Dance Reaction of Arylbenzoheteroles
  作者：Hikaru Nakahara、Junichiro Yamaguchi

  DOI：10.1021/acs.orglett.2c03442

  日期：2022.11.4