3-(thiophen-2-yl)-2H-chromen-2-one | 91805-18-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(thiophen-2-yl)-2H-chromen-2-one
• 英文别名: 3-(2-Thienyl)-2H-1-benzopyran-2-one；3-thiophen-2-ylchromen-2-one
• CAS: 91805-18-4
• 化学式: C₁₃H₈O₂S
• 分子量: 228.271
• InChiKey: AUISNCGJDLDBGR-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 沸点：
  416.8±33.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(thiophen-2-yl)-2H-chromen-2-one 、 2,3-二甲基-1,3-丁二烯 在 对苯二酚 作用下， 以 二氯甲烷 为溶剂， 70.0 ℃ 、900.0 MPa 条件下， 反应 60.0h， 以85%的产率得到(6aRS,10aSR)-8,9-dimethyl-6a-(thien-2-yl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  3-取代的香豆素在水中和高压条件下的Diels-Alder反应。四氢-6 H-苯并[ c ] chromen-6-ones的未催化途径

  摘要：

  据报道，在9 kbar的压力下，仅在水中和在CH 2 Cl 2中进行的3-取代香豆素1a - g与甲基-1,3-丁二烯2a - c的狄尔斯-阿尔德反应。在水性介质中，通过在150°C下操作可获得令人满意的结果，而在高压下，环加成反应在60-70°C下完成，收率极高（85-95％）。与异戊二烯（2b）的反应总是导致对环加合物的排他性形成，而与（E）-亚戊二烯（2c）的反应仅检测到邻位产物。3-苯基磺酰基香豆素的环加成（图1A）与（ê）-piperylene （2C）允许内被排他地获得的加合物，而-3-羧基- （1B）与反应2C，得到的混合物的相应的内切/外切加合物以58:42的比例在水中，并在高压条件下以45:55的比例。

  DOI：

  10.1021/jo051539o
• 作为产物：
  描述：

  (2-Formylphenyl) 2-thiophen-2-ylacetate 在 溶剂黄146 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 3-(thiophen-2-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis, human monoamine oxidase inhibitory activity and molecular docking studies of 3-heteroarylcoumarin derivatives

  摘要：

  Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. Series of 3-indolyl and 3-thiophenylcoumarins were synthesized and evaluated as inhibitors of the two human MAO isoforms, hMAO-A and hMAO-B. In general, the derivatives were found to be selective hMAO-B inhibitors with IC(50) values in the nanoMolar (nM) to microMolar (mu M) range. Docking experiments were carried out in order to compare the theoretical and experimental affinity of these compounds to the hMAO-B protein. According to our results, docking experiments could be an interesting approach to try to predict the activity of this class of coumarins against MAO-B receptors. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.033

文献信息

• Zn(II)-Catalyzed One-Pot Synthesis of Coumarins from Ynamides and Salicylaldehydes
  作者：Huen Ji Yoo、So Won Youn

  DOI：10.1021/acs.orglett.9b01181

  日期：2019.5.3

  A highly efficient and straightforward synthesis of diversely substituted coumarins from ynamides and salicylaldehydes in the presence of Zn(II) catalyst has been developed. The sulfonamide moiety of ynamides was successfully recycled in this process, serving as an effective traceless directing group for high regioselectivity in the bond-forming event. The advantages of this protocol are good functional

  已经开发了在Zn（II）催化剂存在下由酰胺和水杨醛高效高效地直接合成各种取代的香豆素的方法。在此过程中，成功地将了酰胺的磺酰胺部分进行了再循环，在形成键的过程中，它是有效的无痕导向基团，具有很高的区域选择性。该方案的优点是良好的官能团耐受性，宽泛的底物范围，简单且高产率的反应，磺酰胺的回收/重复使用，廉价催化剂的低催化剂负载量以及这些优点，使该方法更具成本效益且更环保。
• Base-promoted synthesis of coumarins from salicylaldehydes and aryl-substituted 1,1-dibromo-1-alkenes under transition-metal-free conditions
  作者：Jianming Liu、Xin Zhang、Lijun Shi、Muwen Liu、Yuanyuan Yue、Fuwei Li、Kelei Zhuo

  DOI：10.1039/c4cc04377d

  日期：——

  Facile synthesis of coumarin via the tandem reaction of salicylaldehyde with aryl-substituted 1,1-dibromo-1-alkene was developed. This new protocol proceeds smoothly under mild and transition-metal-free conditions, it allows rapid access to coumarins containing various heteroatoms that are more difficult to prepare by traditional methods. Based on the isolated intermediate of 4-(diethylamino)-3-phenylchroman-2-one and detailed mechanistic studies, a credible tandem pathway was proposed.

  开发了一种简单的合成香豆素的方法，利用水杨醛与芳基取代的1,1-二溴-1-烯的串联反应。该新方法在温和且无过渡金属的条件下顺利进行，能够快速合成含有多种杂原子的香豆素，而这些香豆素通过传统方法更难制备。基于分离得到的中间体4-(二乙氨基)-3-苯基克罗莫酮和详细的机理研究，提出了一条可信的串联反应路径。
• A Photochemical Synthesis of 3-Arylcoumarins
  作者：Ji-ben Meng、Mei-gin Shen、De-chao Fu、Zhen-heng Gao、Ru-ji Wang、Hong-gen Wang、Teruo Matsuura

  DOI：10.1055/s-1990-26993

  日期：——

  A number of fluorescent 3-arylcoumarins (3-aryl-2H-1-benzo-pyran-2-ones) have been synthesized by the photo-coupling of 3-bromocoumarin with aromatic and heteroaromatic compounds. The structure of 3-(1-naphthyl)coumarin was confirmed by X-ray crystallography.

  通过 3-溴香豆素与芳香族和杂芳香族化合物的光偶联反应，合成了多种荧光 3-芳基香豆素（3-芳基-2H-1-苯并吡喃-2-酮）。X 射线晶体学证实了 3-(1-萘基)香豆素的结构。
• ADHESIVE COMPOSITION FOR DENTAL USE
  申请人：KURARAY NORITAKE DENTAL INC.

  公开号：US20210145701A1

  公开（公告）日：2021-05-20

  The present invention provides a dental adhesive composition that, even after photocuring with a high-output LED irradiator, shows high bond strength not only for dentin untreated by phosphoric acid etching but also for dentin treated by phosphoric acid etching. The present invention relates to a dental adhesive composition comprising a phosphoric acid group-containing polymerizable monomer (A), the phosphoric acid group-containing polymerizable monomer (A) comprising: a dihydrogen phosphate monoester group-containing polymerizable monomer (A-1) represented by general formula (1); a hydrogen phosphate diester group-containing polymerizable monomer (A-2) represented by general formula (2); and a phosphoric acid tetraester group-containing polymerizable monomer (A-3) represented by general formula (3).

  本发明提供了一种牙科粘接剂组合物，即使经过高输出LED辐射器的光固化，也能显示出高的粘接强度，不仅适用于未经过磷酸蚀刻处理的牙本质，还适用于经过磷酸蚀刻处理的牙本质。本发明涉及一种牙科粘接剂组合物，包括含磷酸基可聚合单体（A），其中磷酸基可聚合单体（A）包括：一种由通式（1）表示的二氢磷酸单酯基可聚合单体（A-1）；一种由通式（2）表示的氢磷酸双酯基可聚合单体（A-2）；以及一种由通式（3）表示的磷酸四酯基可聚合单体（A-3）。
• DENTAL MILL BLANK AND METHOD FOR PRODUCING SAME
  申请人：Kuraray Noritake Dental Inc.

  公开号：EP3733114A1

  公开（公告）日：2020-11-04

  The present invention provides a dental mill blank that exhibits desirable resistance against wear in opposing teeth. The present invention relates to a dental mill blank comprising: an inorganic filler containing an inorganic filler (A) and an inorganic filler (B); and a polymer, the inorganic filler (A) partly forming an aggregate, and the dental mill blank satisfying the following formulae (I) to (III), 0.001≤a<0.32 0.3≤b≤10 5≤x≤80 where a is an average primary particle diameter of the inorganic filler (A) in micrometers, b is an average primary particle diameter of the inorganic filler (B) in micrometers, and x is an average particle diameter of the aggregate in micrometers. Preferably, the dental mill blank comprises an island component containing the aggregate, and a sea component containing the inorganic filler (A) and the inorganic filler (B).

  本发明提供了一种牙科铣床坯料，该坯料具有理想的抗对齿磨损性能。本发明涉及一种牙科铣床坯料，包括 无机填料，包含无机填料 (A) 和无机填料 (B)；以及 聚合物、 无机填料（A）部分形成聚集体，牙科研磨坯料满足下式（I）至（III），0.001≤a<0.32 0.3≤b≤10 5≤x≤80 其中，a 是无机填料（A）的平均主颗粒直径（以微米为单位），b 是无机填料（B）的平均主颗粒直径（以微米为单位），x 是聚集体的平均颗粒直径（以微米为单位）。 牙科研磨坯料最好由包含骨料的岛状部分和包含无机填料（A）和无机填料（B）的海状部分组成。