6-bromo-3-(4-methoxybenzoyl)-2H-chromen-2-one | 1245726-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-3-(4-methoxybenzoyl)-2H-chromen-2-one
• 英文别名: 6-Bromo-3-(4-methoxybenzoyl)chromen-2-one
• CAS: 1245726-72-0
• 化学式: C₁₇H₁₁BrO₄
• 分子量: 359.176
• InChiKey: NDVABKYZYXHTQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  56.51
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-bromo-3-(4-methoxybenzoyl)-2H-chromen-2-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以73%的产率得到6-bromo-3-(4-hydroxybenzoyl)coumarin
  参考文献：
  名称：

  Synthesis and Electrochemical and Biological Studies of Novel Coumarin–Chalcone Hybrid Compounds

  摘要：

  A series of novel hydroxy-coumarin chalcone hybrid compounds 2a-i has been synthesized by employing a simple and efficient methodology. An electrochemical characterization using cyclic voltammetry and ESR spectroscopy were carried out to characterize the oxidation mechanism for the target compounds. The antioxidant capacity and reactivity were determined by ORAC and ESR assays, respectively. Biological assays were assessed to evaluate the cytotoxicity and cytoprotection capacity against ROS/RNS on BAEC. The results revealed that all tested compounds present ORAC values that are much higher than other well-known antioxidant compounds such as quercetin and catechin. Compound 2e showed the highest ORAC value (14.1) and also presented a low oxidation potential, good scavenging capacity against hydroxyl radicals, low cytotoxicity, and high cytoprotective activity.

  DOI：

  10.1021/jm400546y
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 indium(III) chloride 、 sodium hydride 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.0h， 生成 3-(4-methoxybenzoyl)-6-bromo-2H-chromene-2-thione 、 6-bromo-3-(4-methoxybenzoyl)-2H-chromen-2-one
  参考文献：
  名称：

  在无溶剂条件下通过InCl 3催化的β-氧二硫代酯环化反应制得高度官能化的2 H-苯二甲基-2-硫酮的简便方法

  摘要：

  通过β-氧代二硫代酯与水杨醛/α-的缩合反应，开发出了一种方便的一锅合成3-芳酰基/杂芳酰基-2 H-亚甲基-2-硫酮和苯并[ f ] 2 H-亚甲基-2-硫酮的方法。在无溶剂条件下在三氯化铟存在下生成羟基萘醛。该反应操作简便，易于扩展，可快速进入差异取代的亚甲基-2-硫酮骨架。

  DOI：

  10.1016/j.tet.2010.11.055

文献信息

• Diastereoselective Synthesis of Rauhut–Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives
  作者：Shu-Mei Yang、Ganapuram Madhusudhan Reddy、Meng-Hsien Liu、Tzu-Ping Wang、Jhen-Kuei Yu、Wenwei Lin

  DOI：10.1021/acs.joc.6b02526

  日期：2017.1.6

  highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut–Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those

  为有效合成Rauhut-Currier型加合物，提出了一种新颖的碱催化且高度非对映选择性的直接Michael加成异构序列。观察到在3-酰基香豆素衍生物上意外地将γ-丁内酰胺α-加成，而不是更普遍的γ-加成。加合物可以进一步进行水解/脱羧以产生与通过将γ-丁内酰胺α加成到相应的查耳酮上所获得的产物等同的产物。
• Enantioselective Synthesis of Polysubstituted Benzopyrano[3,4-<i>c</i>]pyrrolidine Frameworks via [3 + 2] Cycloaddition of Azomethine Ylides and Coumarin Derivatives
  作者：Geng-Hua Chang、Chein-Yi Wang、G. Madhusudhan Reddy、Yi-Ling Tsai、Wenwei Lin

  DOI：10.1021/acs.joc.6b02041

  日期：2016.10.21

  benzopyrano[3,4-c]pyrrolidine derivatives via organocatalyzed [3 + 2] cycloaddition has been achieved. Cinchona alkaloid-derived organocatalysts as Brønsted bases have been examined for this asymmetric cycloaddition of o-hydroxy aromatic aldimines with 3-substituted coumarins. An unexpected rearrangement of the quaternary acyl moiety in the products resulted in an in situ protection of the o-hydroxy group.

  通过有机催化的[3 + 2]环加成反应实现了对苯并吡喃并[3,4- c ]吡咯烷衍生物的对映选择性合成。已经检查了金鸡纳生物碱衍生的有机催化剂作为布朗斯台德碱，该邻位羟基芳族醛亚胺与3-取代的香豆素的不对称环加成反应。产物中季酰基部分的意外重排导致原位保护邻羟基。
• Syntheses of furo[3,4-c]coumarins and related furyl coumarin derivatives via intramolecular Wittig reactions
  作者：Yeong-Jiunn Jang、Siang-en Syu、Yu-Jhang Chen、Mei-Chun Yang、Wenwei Lin

  DOI：10.1039/c1ob06571h

  日期：——

  A new and general strategy for highly functional furo[3,4-c]coumarins and related furyl coumarin derivatives has been developed, which is based on an extraordinarily facile intramolecular Wittig reaction, starting from α,β-unsaturated ketones, tributylphosphine, and acyl chlorides. The phosphorus ylides were proposed to be the key intermediates for constructing the crucial furan ring, leading to a

  已经开发了一种新的，通用的功能性呋喃[3,4- c ]香豆素和相关呋喃香豆香豆素衍生物的新策略，该策略基于从α，β-不饱和酮开始的极其容易的分子内Wittig反应，三丁基膦和酰氯。有人提出磷化磷是构成关键呋喃环的关键中间体，一步就可以制得各种各样的呋喃香豆素。