6-氯查尔酮-3-羧酸 | 51085-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 6-氯查尔酮-3-羧酸
• 中文别名: 6-氯-4-氧代-4H-亚甲基-3-羧酸
• 英文名称: 6-chloro-4-oxo-4H-chromene-3-carboxylic acid
• 英文别名: 6-Chlorchromon-3-carbonsaeure；6-Chlor-4-oxo-4H-1-benzopyran-3-carbonsaeure；6-chlorochromone-3-carboxylic acid；6-chloro-4-oxochromene-3-carboxylic acid
• CAS: 51085-92-8
• 化学式: C₁₀H₅ClO₄
• 分子量: 224.6
• InChiKey: ATDTYCFXRNCJHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  6-氯查尔酮-3-羧酸 在 一水合肼 、 溶剂黄146 作用下， 反应 0.05h， 以87%的产率得到8-chlorochromeno[4,3-c]pyrazol-3(2H)-one
  参考文献：
  名称：

  Insecticidal lead identification by screening benzopyrano[4,3-c] pyrazol-3(2H)-ones library constructed from multiple-parallel synthesis under microwave irradiation

  摘要：

  A rapid library-generation via liquid-phase multiple-parallel synthesis of 2-(substituted)benzyl-1-benzopyrano[4,3-c]pyrazol-3(2H)-ones, bearing two points of diversity, under microwave irradiation was successfully performed using chromenone-3-carboxylic acids as starting materials. Compared to an identical library generated by conventional parallel synthesis, microwave-assisted parallel synthesis dramatically decreased reaction times from an average of 16 h to 13 min, and the yields of products and intermediates were improved in most cases. A bioassay indicated that the compounds of the library exhibited excellent insecticidal activity against T. cinnabarinus at the dosage of 250 mg L-1, and some compounds still exhibited insecticidal activity when the dosage was reduced to 50 mg L-1. This shows that 2-(substituted) benzyl-1-benzopyrano[4,3-c]pyrazol-3(2H)-ones might be used as lead structures for further optimization. To our knowledge, this is the first report about the application of solution-phase multiple-parallel synthesis under microwave irradiation to construct libraries of benzopyrano-[4,3-c]pyrazol-3(2H)-ones with insecticidal activity. The coupling of microwave technology with liquid-phase parallel synthesis constitutes a novel and particularly attractive avenue for the rapid generation of structurally diverse libraries for lead discovery. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.08.020
• 作为产物：
  描述：

  2-羟基-5-氯苯乙酮 在 sodium chlorite 、 氨基磺酸 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 6-氯查尔酮-3-羧酸
  参考文献：
  名称：

  通过铜双（恶唑啉）催化的 [4 + 2] 环加成对映选择性获得四氢氧蒽酮

  摘要：

  通过铜双（恶唑啉）催化的 chrom-4-one 亲二烯体和 Danishefsky 的二烯的 [4 + 2] 环加成反应，实现了对四氢氧杂蒽酮化合物的高度对映选择性。含四元立构中心的氧代二氢氧吨酮（烯酮）加合物的产率高达 98%，ee 高达 89%。环加合物用于合成四氢氧吨酮，具有新型有机锡介导的 β-酮酯准 Krapcho 脱羧作用，并保留立体化学。Tetrahydroxanthone 是多种生物相关饱和氧杂蒽酮的多功能中间体。

  DOI：

  10.1021/acs.orglett.3c00612

文献信息

• Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones <i>via</i> doubly decarboxylative Giese reaction
  作者：Marek Moczulski、Ewelina Kowalska、Elżbieta Kuśmierek、Łukasz Albrecht、Anna Albrecht

  DOI：10.1039/d1ra05914a

  日期：——

  Doubly decarboxylative, photoredox synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones is described. The reaction involves two independent decarboxylation processes: the first one initiating the cycle and the second completing the process. Visible light, photoredox catalyst, base, anhydrous solvent and inert atmosphere constitute the key parameters for the success of the developed

  描述了 4-取代-chroman-2-ones 和 2-取代-chroman-4-ones 的双脱羧、光氧化还原合成。该反应涉及两个独立的脱羧过程：第一个启动循环，第二个完成该过程。可见光、光氧化还原催化剂、碱、无水溶剂和惰性气氛构成了开发转化成功的关键参数。该协议证明适用于香豆素-3-羧酸和色酮-3-羧酸以及作为相应烷基自由基前体的N- (酰氧基) 邻苯二甲酰亚胺。
• Decarboxylative Aminocatalytic Cascade for the Synthesis of Dihydroxanthones
  作者：Anna Albrecht、Jan Bojanowski

  DOI：10.1002/adsc.201700400

  日期：2017.9.4

  A novel decarboxylative aminocatalytic strategy for the synthesis of 4,4a‐dihydroxanthones is described. It was realized by employing dienamine activation and utilizes readily available β,β‐disubstituted enals and chromone‐3‐carboxylic acids as starting materials. A decarboxylation reaction is the key step of the cascade making the aminocatalyst turnover possible.

  描述了一种合成4,4a-dihydroxanthones的新型脱羧氨基催化策略。它是通过使用二烯胺活化而实现的，并利用了现成的β，β-二取代的烯醛和色酮3-羧酸作为起始原料。脱羧反应是级联反应的关键步骤，使氨基催化剂的转化成为可能。
• Synthesis and antimicrobial activity of chromone-linked 2-pyridone fused with 1,2,4-triazoles, 1,2,4-triazines and 1,2,4-triazepines ring systems
  作者：Tarik El-Sayed Ali、Magdy Ahmed Ibrahim

  DOI：10.1590/s0103-50532010000600010

  日期：——

  Three series of novel fused nitrogen heterocyclic systems such as 1,2,4-triazolo[1,5-α ] pyridines (5-7 and 9), pyrido[1,2-b][1,2,4]triazines (10, 11, 13 and 15), and pyrido[1,2-b][1,2,4]triazepines (17, 18, 20 and 22) linked with a chromone moiety were synthesized from the key intermediate 1,6-diamino-(6-chloro-4-oxo-4H-chromen-3-yl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile (4) with some electrophilic

  三组新颖的稠合氮杂环系统，例如1,2,4-三唑并[1,5-α]吡啶（5-7和9），吡啶并[1,2-b] [1,2,4]三嗪（ 10、11、13和15）和与色酮部分连接的吡啶并[1,2-b] [1,2,4]三氮杂20（17、18、20和22）由关键中间体1,6-合成二氨基-（6-氯-4-氧代-4H-铬-3-基）-2-氧代-1,2-二氢吡啶-3,5-二碳腈（4）和一些亲电试剂。通过元素分析和光谱数据确定了新型化合物的结构。还对所有产品的抗微生物活性进行了体外筛选。与参考药物相比，化合物7、9和15表现出最高的活性。
• Synthesis and insecticidal activity of chromanone and chromone analogues of diacylhydrazines
  作者：Pei-Liang Zhao、Jing Li、Guang-Fu Yang

  DOI：10.1016/j.bmc.2007.01.008

  日期：2007.3

  design, synthesis, and insecticidal activities of a series of chromanone and chromone analogues of diacylhydrazine derivatives. The preliminary bioassay showed that some of the chromanone analogues exhibited good insecticidal activity against Mythima separata at the dosage of 500 mg L-1. The present work demonstrated that replacement of the chroman ring of ANS-118, a commercial insecticide, with chromanone

  二酰基肼衍生物已被确定为最重要的昆虫生长调节剂之一。近年来，由于其独特的作用机理，简单的结构和良好的环境特性，设计并合成了多种二酰基肼衍生物。本文介绍了二酰基肼衍生物的一系列苯并二氢吡喃酮和色酮类似物的分子设计，合成和杀虫活性。初步的生物分析表明，某些苯并二氢吡喃酮类似物在剂量为500 mg L-1时对分离的粘膜霉菌具有良好的杀虫活性。目前的工作表明，用苯并二氢吡喃酮部分取代商业杀虫剂ANS-118的苯并二氢吡喃环可以产生具有高杀虫活性的新化合物。
• Doubly Decarboxylative Synthesis of 4-(Pyridylmethyl)chroman-2-ones and 2-(Pyridylmethyl)chroman-4-ones under Mild Reaction Conditions
  作者：Jan Bojanowski、Anna Albrecht

  DOI：10.3390/molecules26154689

  日期：——

  The doubly decarboxylative Michael–type addition of pyridylacetic acid to chromone-3-carboxylic acids or coumarin-3-carboxylic acids has been developed. This protocol has been realized under Brønsted base catalysis, providing biologically interesting 4-(pyridylmethyl)chroman-2-ones and 2-(pyridylmethyl)chroman-4-ones in good or very good yields. The decarboxylative reaction pathway has been confirmed

  已开发出吡啶乙酸与色酮-3-羧酸或香豆素-3-羧酸的双脱羧迈克尔型加成。该协议已在 Brønsted 碱催化下实现，以良好或非常好的收率提供生物学上有趣的 4-(pyridylmethyl)chroman-2-ones 和 2-(pyridylmethyl)chroman-4-ones。脱羧反应途径已通过机理研究得到证实。此外，还描述了开发级联的对映选择性变体的尝试。