3-(benzo[d]thiazol-2-yl)-6-methoxy-2H-chromen-2-one

• 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-(benzo[d]thiazol-2-yl)-6-methoxy-2H-chromen-2-one
• 英文别名: 3-benzothiazol-2-yl-6-methoxycoumarin；3-(2-Benzothiazolyl)-6-methoxycoumarin；3-(1,3-benzothiazol-2-yl)-6-methoxychromen-2-one
• 化学式: C₁₇H₁₁NO₃S
• mdl: MFCD01241736
• 分子量: 309.345
• InChiKey: HKOKDCKQIDYUFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  76.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基苯硫醇 在 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 3-(benzo[d]thiazol-2-yl)-6-methoxy-2H-chromen-2-one
  参考文献：
  名称：

  Preparation and Characterization of Substituted 3-Benzothiazol-2-Ylcoumarins

  摘要：

  AbstractA series of substituted 3‐benzothiazolylcoumarins was prepared from condensation of 2‐hydroxy‐benzaldehyde and 2‐cyanomethylbenzothiazole to investigate the effect of the nature and position of substituents on their absorption and fluorescent behavior. Compounds with a substituent containing a heteroatom which attached at the C6 position showed a split broad absorption band. Solutions of these compounds in various solvents exhibited brilliant blue fluorescence. The emission intensity for compounds with an alkoxy group at the C6 or C7 position in DMF was approximately 7‐ and 15‐fold higher than for the corresponding precursor and quinine sulfate solution, respectively. These compounds also exhibit high thermal stability in solid state.

  DOI：

  10.1002/jccs.201000033

文献信息

• Alumina as a Support and Catalyst for the Synthesis of Benzothiazoles in Solvent-free Condition
  作者：Mei-Fang Ding、Chia-Pei Chen、Shaw-Tao Lin

  DOI：10.1002/jccs.201200413

  日期：2013.6

  and benzothiazolylcoumarins (5) were prepared by the condensation of 2‐aminothiophenol (1) and hydroxybenzaldehydes (2) and 3‐ethoxycarbonylcoumarinnin (3), respectively, in solvent‐free condition. Of the solid support used, γ‐Al2O3 demonstrated the best activity. A linear regression line obtained from correlation between relative formation rate and Hammett constants with slope of 0.653 suggested that

  Arylbenzothiazole（4）和benzothiazolylcoumarins（5）通过2-氨基苯硫酚（的缩合制备1）和羟基苯甲醛（2）和3- ethoxycarbonylcoumarinnin（3），分别在无溶剂的条件。所用的固体支持物，在γ-Al 2 ö 3展示了最佳活性。由相对形成速率和具有0.653斜率的Hammett常数之间的相关性获得的线性回归线表明，由于固态极化效率低，该缩合过程对苯环上的取代基较不敏感。通常，形成4可获得良好的收率（> 80％的收率）。相反，产量5很差，因为γ-Al系的2 ö 3的催化分解3，以形成2（不含P 2 ö 5）和香豆素（以P 2 ö 5）。
• Direct C–H cross-coupling approach to heteroaryl coumarins
  作者：Minsik Min、Bomi Kim、Sungwoo Hong

  DOI：10.1039/c2ob07137a

  日期：——

  A Pd-catalyzed direct cross-coupling of 3-bromocoumarins with heteroarenes provided an efficient route to synthesizing 3-heteroarylcoumarins. The reaction scope for the transformation was fairly broad, affording modest to good yields of various 3-heteroarylcoumarin scaffolds, which are privileged structures and prevalent motifs in many biologically active compounds and fluorophores.

  钯催化的 3-溴香豆素与杂环戊烯的直接交叉偶联为合成 3-杂芳基香豆素提供了一条有效途径。该转化反应的范围相当广泛，可获得各种 3-杂芳基香豆素支架，产率从中等到较高，这些支架是许多生物活性化合物和荧光团中的特优结构和流行主题。
• Tailoring C-6-Substituted Coumarin Scaffolds for Novel Photophysical Properties and Stimuli-Responsive Chromism
  作者：Ravinder Singh、Deng-Gao Chen、Chun-Hsiang Wang、Yi-Cheng Lan、Yi-Hung Liu、Pi-Tai Chou、Chao-Tsen Chen

  DOI：10.1021/acs.jpcb.1c08133

  日期：2021.10.21

  transfer with a large change of dipole moment (Δμ ∼ 18.23 D), hence displaying remarkable emission solvatochromism from the green (536 nm in cyclohexane) to far-red region (714 nm in dimethyl sulfoxide) and a high-temperature sensitivity (−0.23 nm °C–1). These, together with unique basicity and acido-/vaporchromism upon acidification elucidated by NMR and photospectroscopic studies, show stark contrast to

  一种明智的策略被用来设想取代基对基于 2 H -chromen-2-one-3-苯并噻唑支架的推拉框架的光物理性质的显着区域位置影响，命名为6-X-CUMs。其中，6-NEt 2 -CUM显示出显着的激发态分子内电荷转移，偶极矩变化很大（Δμ ∼ 18.23 D），因此从绿色（环己烷中为 536 nm）到远红色区域显示出显着的发射溶剂致变色（在二甲基亚砜中为 714 nm）和高温灵敏度（-0.23 nm °C –1）。这些，连同 NMR 和光谱研究阐明的酸化时独特的碱性和酸/蒸汽变色，与传统的7-NEt 2 -CUM形成鲜明对比。这些定制的6-X-CUM的新系列代表了定制光物理特性以开发一类有前途的多刺激响应材料的新维度。
• Recyclization of 2-imino-2H-1-benzopyrans using nucleophilic reagents 3. Reaction of 2-iminocoumarin-3-carboxamides with o-phenylenediamines and o-amino(thio)phenols
  作者：S. N. Kovalenko、M. V. Vasil'ev、I. V. Sorokina、V. P. Chernykh、A. V. Turov、S. A. Rudnev

  DOI：10.1007/bf02317811

  日期：1998.12