2-乙酰基苯基噻吩-2-羧酸酯 | 77708-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙酰基苯基噻吩-2-羧酸酯
• 英文名称: 2--acetophenon
• 英文别名: Thiophene-2-carboxylic acid, 2-acetylphenyl ester；(2-acetylphenyl) thiophene-2-carboxylate
• CAS: 77708-28-2
• 化学式: C₁₃H₁₀O₃S
• 分子量: 246.287
• InChiKey: PCRBEFCJXDCGOM-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114 °C
• 沸点：
  431.2±25.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-乙酰基苯基噻吩-2-羧酸酯 在 吡啶 、 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 为溶剂， 生成 3-isobutyl-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one
  参考文献：
  名称：

  多功能Chromeno[2,3-c]pyrrol-9(2H)-ones的合成：4-(二甲氨基)吡啶催化Baker-Venkataraman重排反应的研究与应用

  摘要：

  描述了从 1,3-二芳基-1,3-二酮和氨基酸中高效一锅合成多功能 chromeno[2,3-c]pyrrol-9(2H)-ones。该合成基于 4-（二甲氨基）吡啶催化的 Baker-Venkataraman 重排和后续反应。

  DOI：

  10.1002/ejoc.201100435
• 作为产物：
  描述：

  2-噻吩甲酸 在 草酰氯 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.08h， 生成 2-乙酰基苯基噻吩-2-羧酸酯
  参考文献：
  名称：

  论地色酮的乙烯基亚砜侧链对其生物活性的作用

  摘要：

  制备了 dirchromone 的类似物，以阐明其特殊的乙烯基亚砜侧链对其细胞毒性和抗菌特性的关键作用，特别是取决于硫的存在和氧化状态。dirchromone 与半胱胺的反应揭示了令人惊讶的迈克尔受体行为，消除了甲基亚磺酰基部分和硫原子的氧化还原转化，这可能与 dirchromone 在细胞内的作用方式有关。

  DOI：

  10.1039/d0ob01783c

文献信息

• Synthesis and reactivity of 1-aryl-9H-thieno[3,4-b]chromon-9-ones
  作者：Mikhail M. Krayushkin、Konstantin S. Levchenko、Vladimir N. Yarovenko、Ludmila V. Christoforova、Valery A. Barachevsky、Yury A. Puankov、Tatyana M. Valova、Olga I. Kobeleva、K. Lyssenko

  DOI：10.1039/b9nj00237e

  日期：——

  Methods were developed for the synthesis of 1-aryl-9H-thieno[3,4-b]chromon-9-ones based on the reaction of bromo and dibromo derivatives of 2-methyl-4H-chromon-4-one with thioacetamide in DMF. The thienochromones were modified and their fluorescence properties were studied. Bis(thienochromones) were synthesized by the reaction of thienochromones with ketoaldehydes.

  根据 2-甲基-4H-色-4-酮的溴和二溴衍生物与硫代乙酰胺在 DMF 中的反应，开发了合成 1-芳基-9H-噻吩并[3,4-b]色-9-酮的方法。对这些噻吩一氢色酮进行了修饰，并研究了它们的荧光特性。双（噻吩一氢色酮）是通过噻吩一氢色酮与酮醛反应合成的。
• Synthesis, photophysical and electrochemical properties of novel and highly fluorescent difluoroboron flavanone β-diketonate complexes
  作者：Elida Betania Ariza Paez、Sergio Curcio、Natália P. Neme、Matheus J. S. Matos、Rodrigo S. Correa、Fabio Junio Pereira、Flaviane Francisco Hilário、Thiago Cazati、Jason Guy Taylor

  DOI：10.1039/d0nj03525d

  日期：——

  and fast synthesis of difluoroboron β-diketonate (BF2dbm) complexes makes their applications even more attractive. Although many different types of difluoroboron β-diketonates complexes have been studied, the cyclic flavanone analogues of these compounds have never been reported in the literature. Therefore, the present work aims to synthesize difluouroboron flavanone β-diketonate complexes, study their

  β-二酮硼酸二氟硼酸酯配合物具有高度的发光性，具有广泛的特性，例如在溶液中和在固态时均具有荧光，并且具有高的摩尔消光系数。由于它们具有丰富的光学特性，因此已针对这些化合物在有机电子产品中的应用进行了研究，例如自组装以及在生物传感器，生物成像和光电设备中的应用。简便快速合成β-二酮硼二氟硼酸（BF 2dbm）复合体使其应用程序更具吸引力。尽管已经研究了许多不同类型的二氟硼β-二酮酸酯络合物，但是这些化合物的环状黄烷酮类似物从未在文献中报道。因此，本工作旨在合成双氟硼龙黄酮β-二酮酸酯配合物，研究其光物理和电化学性质，并评估其在光电设备中的适用性。合成基于贝克-文卡塔拉曼（Baker-Venkataraman）反应，该反应最初提供取代的二酮，随后将其与醛反应以提供拟议的黄烷酮。通过使黄烷酮与BF 3 ·Et 2反应实现络合总共获得了9种新化合物。将代表性的二氟硼黄烷酮配合物进行单晶X射线衍射以
• Synthesis and properties of photosensitive compounds based on bromine-containing 3-acyl-2-furylchromones
  作者：K. S. Levchenko、V. A. Barachevski、V. N. Yarovenko、M. M. Krayushkin、I. S. Semenova、O. I. Kobeleva、T. M. Valova、P. S. Shmelin

  DOI：10.1007/s10593-011-0736-x

  日期：2011.5

  Methods have been developed for the synthesis of new photosensitive compounds based on the reaction of N,S,O-nucleophiles with 3-acyl-2-(5-bromofur-2-yl)chromones and 3-acyl-2-(5-bromomethylfur-2-yl)chromones. The relationship between the spectral properties and the structure of compounds has been shown.

  已经开发了基于N，S，O-亲核试剂与3-酰基-2-（5-溴糠-2-基）色酮和3-酰基-2-（5-溴甲基糠-2-基）色酮。已经显示出光谱性质与化合物结构之间的关系。
• Discovery of 3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one as a phosphodiesterase-5 inhibitor and its complex crystal structure
  作者：Na-Na Shang、Yong-Xian Shao、Ying-Hong Cai、Matthew Guan、Manna Huang、Wenjun Cui、Lin He、Yan-Jun Yu、Lei Huang、Zhe Li、Xian-Zhang Bu、Hengming Ke、Hai-Bin Luo

  DOI：10.1016/j.bcp.2014.02.013

  日期：2014.5

  Phosphodiesterase-5 (PDE5) inhibitors have been approved for the treatment of erectile dysfunction and pulmonary hypertension, but enthusiasm on discovery of PDE5 inhibitors continues for their potential new applications. Reported here is discovery of a series of new PDE5 inhibitors by structure-based design, molecular docking, chemical synthesis, and enzymatic characterization. The best compound, 3(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one (57), has an IC50 of 17 nM against the PDE5 catalytic domain and good selectivity over other PDE families. The crystal structure of the PDE5 catalytic domain in complex with 57 was determined at 2 angstrom resolution and showed that 57 occupies the same pocket as other PDE5 inhibitors, but has a different binding pattern in detail. On the basis of the binding pattern of 57, a novel scaffold can be proposed as a candidate of PDE inhibitors. (C) 2014 Elsevier Inc. All rights reserved.
• Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones
  作者：David S. Clarke、Christopher D. Gabbutt、John D. Hepworth、B. Mark Heron

  DOI：10.1016/j.tetlet.2005.06.058

  日期：2005.8

  3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.