5-formyl-5'-(4-methoxyphenyl)-2,2'-bithiophene | 1133874-06-2

• 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-formyl-5'-(4-methoxyphenyl)-2,2'-bithiophene
• 英文别名: 5'-(4-Methoxyphenyl)-[2,2'-bithiophene]-5-carbaldehyde；5-[5-(4-methoxyphenyl)thiophen-2-yl]thiophene-2-carbaldehyde
• CAS: 1133874-06-2
• 化学式: C₁₆H₁₂O₂S₂
• 分子量: 300.402
• InChiKey: GKPSACHHYYXJPK-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C
• 沸点：
  466.4±45.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-formyl-5'-(4-methoxyphenyl)-2,2'-bithiophene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到5'-(4-hydroxyphenyl)-[2,2'-bithiophene]-5-carbaldehyde
  参考文献：
  名称：

  钯催化的两个富电子杂芳烃之间的氧化交叉偶联†

  摘要：

  具有相似结构和电子特性的两个偶联配偶之间的过渡金属催化的氧化交叉偶联由于难以抑制不希望的均相偶联而仍然是一个挑战。我们在本文中报道了在温和的反应条件下，两个噻吩之间的Pd催化的氧化交叉偶联。这种方法也可以扩展到呋喃。该反应的一些显着优点在于其合成简单，省去了有毒的锡烷偶联伙伴，并且具有出色的官能团相容性。该协议的特征使其成为构建电子和光电子材料中感兴趣的2,2'-噻吩-噻吩键合的理想策略。

  DOI：

  10.1039/c3sc51278a
• 作为产物：
  描述：

  4-甲氧基苯硼酸 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四(三苯基膦)钯 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 5-formyl-5'-(4-methoxyphenyl)-2,2'-bithiophene
  参考文献：
  名称：

  Development of dual targeting inhibitors against aggregations of amyloid-β and tau protein

  摘要：

  Aggregations of both amyloid-beta (A beta) and hyper-phosphorylated tau proteins are recognized as key pathological manifestations of Alzheimer's disease (AD). Agents that inhibit both those forms of aggregation show promise as drug candidates. Seventeen oligo heteroaromatic compounds were rapidly synthesized via a one-pot, 3- or 4-component coupling procedure. Evaluations showed that compounds E16 and E18 were the most potent inhibitors of A beta and tau aggregations (E16: IC(50)s = 0.38, 0.29 mu M against A beta, tau, respectively, E18: IC(50)s = 0.55, 0.30 mu M against A beta, tau, respectively). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.095

文献信息

• Synthesis of 5-aryl-5′-formyl-2,2′-bithiophenes as new precursors for nonlinear optical (NLO) materials
  作者：Cyril Herbivo、Alain Comel、G. Kirsch、M. Manuela M. Raposo

  DOI：10.1016/j.tet.2008.12.078

  日期：2009.3

  A series of formyl-substituted 5-aryl-2,2′-bithiophenes 5 were synthesized using two different methods: Vilsmeier–Haack–Arnold reaction (VHA) or through Suzuki coupling. The synthesis of compounds 5 through the Vilsmeier–Haack–Arnold reaction, starting from inexpensive and easily available precursors such as acetophenones, gave the title compounds in low yields after four reaction steps. On the other

  使用两种不同的方法：Vilsmeier–Haack–Arnold反应（VHA）或通过Suzuki偶联合成了一系列被甲酰基取代的5-芳基-2,2'-联噻吩5。通过Vilsmeier-Haack-Arnold反应进行的化合物5的合成，是从廉价且容易获得的前体（如苯乙酮）开始的，经过四个反应步骤后，标题化合物的收率很低。另一方面，官能化的芳基硼酸7和5-溴-5'-甲酰基-2,2'-联噻吩6的Suzuki偶联仅一步就得到了高产率的化合物5。
• Blood-brain barrier permeable peptide compositions comprising a VAB domain of an anti-amyloid-beta camelid single-domain heavy-chain only antibody
  申请人：ICB International, Inc.

  公开号：US10738109B2

  公开（公告）日：2020-08-11

  Blood-brain barrier permeable peptide compositions that contain variable antigen binding domains from camelid and/or shark heavy-chain only single-domain antibodies are described. The variable antigen binding domains of the peptide compositions bind to therapeutic and diagnostic biomarkers in the central nervous system, such as the amyloid-beta peptide biomarker for Alzheimer's disease. The peptide compositions contain constant domains from human IgG, camelid IgG, and/or shark IgNAR. The peptide compositions include heavy-chain only single-domain antibodies and compositions with one or more variable antigen binding domain bound to one or more constant domains.

  本文描述了血脑屏障可渗透多肽组合物，该组合物含有来自驼科和/或鲨鱼重链单域抗体的可变抗原结合域。多肽组合物的可变抗原结合域可与中枢神经系统中的治疗和诊断生物标志物结合，如阿尔茨海默病的淀粉样蛋白-β肽生物标志物。多肽组合物含有人类 IgG、驼科动物 IgG 和/或鲨鱼 IgNAR 的恒定结构域。多肽组合物包括只有重链的单结构域抗体，以及一个或多个可变抗原结合结构域与一个或多个恒定结构域结合的组合物。
• Synthesis and characterization of novel, thermally stable 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5′-dicyanovinyl-2,2′-bithiophenes as potentially promising non-linear optical materials
  作者：Cyril Herbivo、Alain Comel、G. Kirsch、A. Maurício C. Fonseca、M. Belsley、M. Manuela M. Raposo

  DOI：10.1016/j.dyepig.2010.01.006

  日期：2010.8

  Two series of dicyanovinyl-substituted compounds namely 2-aryl-5-dicyanovinylthiophenes and 5-aryl-5'-dicyanovinyl-2,2'-bithiophenes were synthesized through Knoevenagel condensation of the corresponding 2-aryl-5-formyl-thiophenes and 5-aryl-5'-formyl-2,2'-bithiophene precursors. In contrast, the 2-aryl-5-formyl-thiophenes precursor were prepared through the Vilsmeier Haack Arnold reaction starting from inexpensive and easily available precursors such as acetophenones; this method produced the title compounds in higher yield than that recently reported which involved the Suzuki coupling of functionalized aryl boronic acids with 5-bromo-2-formyl-thiophene. Electrochemical studies and characterization of both the linear and non-linear optical properties and thermal properties indicated that good non-linearity was complemented by exceptional thermal stability for some chromophores, making them potential candidates for several optoelectronic applications such as solvatochromic probes and non-linear optical materials. (C) 2010 Elsevier Ltd. All rights reserved.
• BLOOD-BRAIN BARRIER PERMEABLE PEPTIDE COMPOSITIONS
  申请人：ICB International, Inc.

  公开号：EP3309171B1

  公开（公告）日：2021-06-09
• Pd-catalyzed oxidative cross-coupling between two electron rich heteroarenes
  作者：Chun-Yang He、Zhen Wang、Cai-Zhi Wu、Feng-Ling Qing、Xingang Zhang

  DOI：10.1039/c3sc51278a

  日期：——

  The transition-metal-catalyzed oxidative cross-coupling between two coupling partners with similar structure and electronic characteristics remains a challenge owing to difficulty in suppressing undesired homo-couplings. We herein report a Pd-catalyzed oxidative cross-coupling between two thiophenes under mild reaction conditions. This approach can also be extended to furans. Some notable advantages

  具有相似结构和电子特性的两个偶联配偶之间的过渡金属催化的氧化交叉偶联由于难以抑制不希望的均相偶联而仍然是一个挑战。我们在本文中报道了在温和的反应条件下，两个噻吩之间的Pd催化的氧化交叉偶联。这种方法也可以扩展到呋喃。该反应的一些显着优点在于其合成简单，省去了有毒的锡烷偶联伙伴，并且具有出色的官能团相容性。该协议的特征使其成为构建电子和光电子材料中感兴趣的2,2'-噻吩-噻吩键合的理想策略。