2,5-bis(4-nitrophenyl)thiophene | 70010-47-8

• 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: 2,5-bis(4-nitrophenyl)thiophene
• CAS: 70010-47-8
• 化学式: C₁₆H₁₀N₂O₄S
• 分子量: 326.332
• InChiKey: FBNOZEYGTWFASC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-bis(4-nitrophenyl)thiophene 在 盐酸 、 氢气 、 palladium(II) hydroxide 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 (2S,2'S)-N,N'-(2,5-thienediyldi-4,1-phenylene)bis(1-(phenylacetyl)-2-pyrrolidinecarboxamide)
  参考文献：
  名称：

  HCV NS5A replication complex inhibitors. Part 3: discovery of potent analogs with distinct core topologies

  摘要：

  In a recent disclosure,(1) we described the discovery of dimeric, prolinamide-based NS5A replication complex inhibitors exhibiting excellent potency towards an HCV genotype 1b replicon. That disclosure dealt with the SAR exploration of the peripheral region of our lead chemotype, and herein is described the SAR uncovered from a complementary effort that focused on the central core region. From this effort, the contribution of the core region to the overall topology of the pharmacophore, primarily vector orientation and planarity, was determined, with a set of analogs exhibiting < 10 nM EC50 in a genotype 1b replicon assay. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.086
• 作为产物：
  描述：

  ω-bromo-para-nitro-acetophenone 在 劳森试剂 、 乙醇 、 六氟异丙醇 、 三乙胺 、 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 190.0h， 生成 2,5-bis(4-nitrophenyl)thiophene
  参考文献：
  名称：

  六氟异丙醇作为溶剂和促进剂在Paal-Knorr合成N-取代的二芳基吡咯中

  摘要：

  据报道，通过Paal-Knorr吡咯合成方法，由通常难溶的相应1,4-二酮可无添​​加剂合成具有挑战性的N-取代的芳基吡咯，该方法利用了1,1,1,3的独特性质，3,3-六氟异丙醇（HFIP）作为溶剂和反应促进剂。我们的程序提供了简单的执行和纯化方法，以及易于放大的规模，可用于Paal-Knorr合成中，结构复杂的许多吡咯，包括中等难度到极高产率的具有挑战性的四和五取代的吡咯。HFIP也可以用作呋喃和噻吩的Paal-Knorr合成中的溶剂。然而，在吡咯的合成中，溶剂作用更为明显。

  DOI：

  10.1016/j.tet.2021.131985

文献信息

• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011082077A1

  公开（公告）日：2011-07-07

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such compounds, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及能够抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物，包括这些化合物的组合物，以及抑制NS5A蛋白功能的方法。
• Synthesis of heterocyclic compounds with adamantane-like cage structures consisting of phosphorus, sulfur, and carbon
  作者：Noriki Kutsumura、Ryuichiro Ohshita、Jumpei Horiuchi、Kotaro Tateno、Naoshi Yamamoto、Tsuyoshi Saitoh、Yasuyuki Nagumo、Hidetoshi Kawai、Hiroshi Nagase

  DOI：10.1016/j.tet.2017.07.016

  日期：2017.8

  consisting of phosphorus, sulfur, and carbon atoms was developed. We examined the reaction of a variety of acetophenone derivatives with P4S10 in refluxing benzene. A novel noradamantane-like cage compound was also synthesized, when the reaction of 2’-methoxyacetophenone with P4S10 was performed in refluxing toluene. In addition, by using the adamantane-like cage compound, 4,4’-dimethoxybenzophenone and N,N-dimethylbenzamide

  开发了由磷，硫和碳原子组成的新型金刚烷类笼状化合物的合成方法。我们研究了各种苯乙酮衍生物与P 4 S 10在回流的苯中的反应。当2'-甲氧基苯乙酮与P 4 S 10的反应在甲苯回流中进行时，也合成了一种新型的金刚烷类笼型化合物。此外，通过使用金刚烷状笼型化合物，4,4'-二甲氧基二和Ñ，Ñ二甲基苯甲酰胺被成功转化到分别对应的硫酮（98％）和苯并硫代酰胺（89％）。
• One-Pot Double Suzuki−Miyaura Couplings: Rapid Access to Nonsymmetrical Tri(hetero)aryl Derivatives
  作者：Floriane Beaumard、Philippe Dauban、Robert H. Dodd

  DOI：10.1021/ol900358n

  日期：2009.4.16

  We describe a one-pot, simultaneous Suzuki−Miyaura cross-coupling of two different aryl boronic acids with symmetrical dibromo aryl and heterocyclic substrates to give as major products the unsymmetrical disubstituted tri(hetero)aryl derivatives. Yields of unsymmetrical dicoupled products were generally in the 52−75% range. This methodology is particularly suited to the generation of chemical libraries

  我们描述了两个不同的芳基硼酸与对称的二溴芳基和杂环底物的一锅式同时进行的Suzuki-Miyaura交叉偶联，以不对称的二取代的三（杂）芳基衍生物为主要产物。非对称双偶合产物的产率通常在52-75％的范围内。该方法特别适合于化学文库的生成以及生物活性或天然产物类似物的合成。
• Hepatitis C Virus Inhibitors
  申请人：Lopez Omar D.

  公开号：US20110294819A1

  公开（公告）日：2011-12-01

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such compounds, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及能够抑制丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物，包括这些化合物的组合物以及抑制NS5A蛋白功能的方法。
• Design, synthesis, and structure–activity relationship of novel thiophene derivatives for β-amyloid plaque imaging
  作者：Rajesh Chandra、Mei-Ping Kung、Hank F. Kung

  DOI：10.1016/j.bmcl.2005.11.055

  日期：2006.3

  Novel 2,5-diphenylthiophene derivatives were synthesized and structure activity relationship with regard to A beta plaque binding was studied. Binding affinities of these compounds were found to range from 3.9 to >1000 nM, depending on the substitution patterns on the phenyl ring. The fluoroethyl-substituted thiophene derivatives showed excellent binding affinities. These compounds may be useful for the development of novel PET tracers for the imaging of beta-amyloid plaques in the brain of patients with Alzheimer's disease. (C) 2005 Elsevier Ltd. All rights reserved.