5-(4-nitrophenyl)thiophene-2-carbaldehyde | 38401-74-0

• 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: 5-(4-nitrophenyl)thiophene-2-carbaldehyde
• CAS: 38401-74-0
• 化学式: C₁₁H₇NO₃S
• mdl: MFCD01860784
• 分子量: 233.247
• InChiKey: JTCFVBWDULLQMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-nitrophenyl)thiophene-2-carbaldehyde 以 乙醇 为溶剂， 生成 9,9-dimethyl-12-[5-(4-nitrophenyl)thiophen-2-yl]-7,8,9,10-tetrahydrobenzo[a]acridin-11(12H)-one
  参考文献：
  名称：

  Synthesis of 12-hetaryl-9,9-dimethyl-7,8,9,10-tetrahydrobenzo[a]acridin-11(12H)-ones

  摘要：

  Three-component condensation of naphthalen-2-amine with 5-arylfuran(thiophene, N-methylpyrrole)-2-carbaldehyde and 5,5-dimethylcyclohexane-1,3-dione, as well as condensation of N-[(5-arylfuran(thiophen)-2-ylmethylidene]naphthalen-2-amine with 5,5-dimethylcyclohexane-1,3-dione gave the corresponding 12-[5-arylfuran(thiophen, N-methylpyrrol)-2-yl]-7,8,9,10-tetradrobenzo[a]acridin-11(12H)-ones.

  DOI：

  10.1134/s107042801406013x
• 作为产物：
  描述：

  2-噻吩甲醛 、 1-溴-4-硝基苯 在 sodium carbonate 、 silver(l) oxide 、 三甲基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以78%的产率得到5-(4-nitrophenyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  From agriculture residue to catalyst support; A green and sustainable cellulose-based dip catalyst for C C coupling and direct arylation

  摘要：

  The core characteristics of a perfect catalyst include good activity, simple design, excellent stability, easy recovery from reaction mixture, recyclability, and have the provision for easy scale up. The ease in synthesis, recyclability and scale up makes the dip catalyst a major contender in this regard which possess most of the aforementioned characteristics. In this work, we report a dip catalyst made of cellulose, isolated from agriculture residue (sugarcane bagasse), in which biogenically synthesized palladium nanoparticles were dispersed. The prepared dip catalyst was characterized by FESEM, EDS, XRD, ATR-IR, TGA, TEM, XPS and ICP-OES analysis. Also, the activity of the dip catalyst was studied in the Suzuki-Miyaura cross-coupling reaction and was found to give excellent conversion with 15 recycles. Further, the activity of dip catalyst in C5-arylation of 2-substituted thiophenes was evaluated for which promising yields were obtained.

  DOI：

  10.1016/j.carbpol.2019.115060

文献信息

• Cyanine–cyanine hybrid structure as a stabilized polyelectrochromic system: synthesis, stabilities, and redox behavior of di(1-azulenyl)methylium units connected with electron-accepting π-electron systems
  作者：Shunji Ito、Ryuta Sekiguchi、Akira Mizushima、Kohei Kudo、Jun Kawakami、Taku Shoji

  DOI：10.24820/ark.5550190.p010.163

  日期：——

  This paper describes preparation of the two-types of cations composed of di(1-azulenyl)methylium units based on a new structural principle of cyanine–cyanine (C–C) hybrid for the design of polyelectrochromic materials. Voltammetric analysis of these cations revealed the idealized reversible two-step, two-electron redox properties. Two-step color changes presumed by their C–C hybrid structure were revealed

  本文描述了基于花青-花青 (C-C) 杂化的新结构原理，制备由二 (1-azulenyl)methylium 单元组成的两种类型的阳离子，用于设计聚电致变色材料。这些阳离子的伏安分析揭示了理想化的可逆两步、两电子氧化还原特性。通过它们的电化学还原揭示了由它们的 C-C 混合结构推测的两步颜色变化。两种类型的例子证明了采用具有薁骨架的新结构原理的稳定化聚电致变色材料的创造范围。
• Method for the Large-Scale Synthesis of Multifunctional 1,4-Dihydro-pyrrolo[3,2-<i>b</i>]pyrroles
  作者：Mariusz Tasior、Olena Vakuliuk、Daiki Koga、Beata Koszarna、Krzysztof Górski、Marek Grzybowski、Łukasz Kielesiński、Maciej Krzeszewski、Daniel T. Gryko

  DOI：10.1021/acs.joc.0c01665

  日期：2020.11.6

  thorough investigation has enabled the optimization of the synthesis of 1,4-dihydro-pyrrolo[3,2-b]pyrroles. Although salts of such metals as vanadium, niobium, cerium, and manganese were found to facilitate the formation of 1,4-dihydro-pyrrolo[3,2-b]pyrroles from amines, aldehydes, and diacetyl, we confirmed that iron salts are the most efficient catalysts. The conditions identified (first step: toluene/AcOH

  彻底的研究已使1,4-二氢-吡咯并[3,2- b ]吡咯的合成最优化。尽管发现钒，铌，铈和锰等金属的盐可促进由胺，醛和二乙酰基形成1,4-二氢-吡咯并[3,2- b ]吡咯，但我们证实铁盐是最有效的催化剂。确定的条件（第一步：甲苯/ AcOH = 1：1，1 h，50°C;第二步：甲苯/ AcOH = 1：1，Fe（ClO 4）3 ·H 2 O，16 h，50°C ）导致四芳基吡咯并[3,2- b ]吡咯的形成，产率为6-69％。首次出现非常富电子的取代基（4-Me 2 NC 6 H4，3-（OH）C 6 H ^ 4，吡咯-2-基）由醛始发和空间位阻的取代基（2-CLC 6 ħ 4，2- BRC 6 ħ 4，2-CNC 6 ħ 4，2-（ CO 2我）C 6 H ^ 4，2-（TMS-C≡C）C 6 H ^ 4）上苯胺本可以被附加到所述吡咯并[3,2- b ]吡咯芯。现在也可以制备带有N-取代基和C的有序排列的1
• A metal-free cascade reaction of β-halo-α,β-unsaturated aldehydes and 1,4-dithiane-2,5-diols: synthesis of polycyclic 2-formylthiophenes
  作者：Limi Goswami、Kashmiri Neog、Kumud Sharma、Pranjal Gogoi

  DOI：10.1039/c7ob01641g

  日期：——

  A metal-free cascade reaction strategy has been developed for the synthesis of novel polycyclic 2-formylthiophenes from β-halo-α,β-unsaturated aldehydes and 1,4-dithiane-2,5-diol. Recyclable polymer supported organic base was used to perform the reaction process. This synthetic protocol was applied to synthesize several novel polycyclic thiophenes including steroidal D-ring annelated thiophene. Our

  已经开发了一种无金属级联反应策略，用于从β-卤代-α，β-不饱和醛和1,4-二噻吩-2,5-二醇合成新型多环2-甲酰基噻吩。使用可回收的聚合物负载的有机碱进行反应过程。该合成方案用于合成几种新型多环噻吩，包括甾体D环退火的噻吩。我们的合成策略可提供高产率的噻吩，避免繁琐的后处理程序并最大程度地减少废物的形成。
• Synthesis and antioxidant activity study of pyrazoline carrying arylfuran/thiophene moiety
  作者：Vidyashree Jois、Balakrishna Kalluraya、K.S. Girisha

  DOI：10.2298/jsc140109090j

  日期：——

  A novel series of N-acetyl-3-aryl-5-(5-(p/o-nitrophenyl)-2-arylfuryl/thienyl) substituted pyrazoline (3a-o) were synthesized by the reaction of 1-aryl-3-(5-(p/o-nitrophenyl)-2-furyl/thienyl)-2-propene-1-one with hydrazine hydrate in acetic acid medium. The structures of the newly synthesized compounds were established by IR, 1H NMR, mass spectra and single crystal X-ray study. The synthesized compounds were subjected to antioxidant activity using DPPH scavenging assay. The compounds 3a, 3f, 3h and 3o showed moderate activity.

  通过 N-乙酰基-3-芳基-5-(5-(对/邻硝基苯基)-2-芳基呋喃基/噻吩基) 反应合成了一系列新型 N-乙酰基-3-芳基-5-(5-(对/邻硝基苯基)-2-芳基呋喃/噻吩基) 1-芳基-3-(5-(对/邻硝基苯基)-2-呋喃基/噻吩基)-2-丙烯-1-酮与肼水合物在乙酸介质中反应合成了吡唑啉（3a-o）。 水合肼在乙酸介质中的反应。通过红外光谱、1 通过红外光谱、1H NMR、质谱和单晶 X 射线研究。用 DPPH 清除剂对合成化合物进行了抗氧化活性测试。 抗氧化活性。化合物 3a、3f、3h 和 3o 显示出中等程度的活性。 活性。
• Non-canonical amino acids bearing thiophene and bithiophene: synthesis by an Ugi multicomponent reaction and studies on ion recognition ability
  作者：Cátia I. C. Esteves、M. Manuela M. Raposo、Susana P. G. Costa

  DOI：10.1007/s00726-017-2392-7

  日期：2017.5

  cations indicated that the bithienyl amino acid bearing a methoxy group is a selective colorimetric chemosensor for Cu2+, while the other (bi)thienyl amino acids act as fluorimetric chemosensors with high sensitivity towards Fe3+ and Cu2+ in a metal–ligand complex with 1:2 stoichiometry. The photophysical and ion sensing properties of these amino acids confirm their potential as fluorescent probes suitable

  通过杂环醛，胺，酸和异氰酸酯之间的多组分Ugi反应获得具有不同取代基的新的噻吩基和二噻吩基氨基酸。由于在侧链上存在硫杂环，这些非天然氨基酸具有很高的发射性，并带有额外的给电子原子，因此测试了它们在识别乙腈和乙腈中生物医学相关离子中作为荧光探针和化学传感器的能力。乙腈/水溶液。在有机和无机阴离子以及碱的存在下，通过分光光度法/分光荧光滴定法获得的结果；碱土金属和过渡金属阳离子表明，带有甲氧基的亚苄基氨基酸是Cu 2+的选择性比色化学传感器，而其他（联）噻吩基氨基酸充当荧光化学传感器，对化学配比为1：2的金属-配体络合物中的Fe 3+和Cu 2+具有高灵敏度。这些氨基酸的光物理和离子感测特性证实了它们作为适合掺入具有化学感应能力的肽构架的荧光探针的潜力。