7-甲基苯并呋喃-3(2H)-酮 | 669-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 7-甲基苯并呋喃-3(2H)-酮
• 英文名称: 7-methylbenzofuran-3(2H)-one
• 英文别名: 7-methyl-1-benzofuran-3-one
• CAS: 669-04-5
• 化学式: C₉H₈O₂
• mdl: MFCD11137731
• 分子量: 148.161
• InChiKey: FRLLIMIJMRLFCC-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 沸点：
  125 °C(Press: 11 Torr)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  7-甲基苯并呋喃-3(2H)-酮 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 8.0h， 以36%的产率得到7-(bromomethyl)benzofuran-3(2H)-one
  参考文献：
  名称：

  Rational Evolution of a Novel Type of Potent and Selective Proviral Integration Site in Moloney Murine Leukemia Virus Kinase 1 (PIM1) Inhibitor from a Screening-Hit Compound

  摘要：

  Serine/threonine kinase PIM1 is an emerging therapeutic target for hematopoietic and prostate cancer therapy. To develop a novel PIM1 inhibitor, we focused on 1, a metabolically labile, nonselective kinase inhibitor discovered in our previous screening study. We adopted a rational optimization strategy based mainly on structural information for the PIM1-1 complex to improve the potency and selectivity. This approach afforded the potent and metabolically stable PIM1-selective inhibitor 14, which shows only a marginal increase in molecular weight compared with 1 but has a significantly decreased cLogP. The validity of our design concept was confirmed by X-ray structure analysis. In a cellular study, 14 potently inhibited the growth of human leukemia cell line MV4-11 but had a negligible effect on the growth of WI-38 (surrogate for general toxicity). These results demonstrate the effectiveness of our design strategy for evolving the screening-hit compound 1 into a novel type of PIM1 inhibitor, 14.

  DOI：

  10.1021/jm3001289
• 作为产物：
  描述：

  3-甲基水杨酸 在 硫酸 、 potassium acetate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 0.5h， 生成 7-甲基苯并呋喃-3(2H)-酮
  参考文献：
  名称：

  微波辅助合成苯并呋喃-3（2H）-ones

  摘要：

  研究了微波条件下合成苯并呋喃-3（2H）-一的新方法。筛选反应条件，并检查苯甲酸酯底物的合格范围。结果表明，该方法可以简便快捷地获得这些重要的二氢苯并呋喃酮，收率为43％至58％。

  DOI：

  10.17344/acsi.2019.5104

文献信息

• An Unusual Triazole Synthesis from Aurones
  作者：Scott T. Handy、Arjun Kafle、Shrijiana Bhattarai

  DOI：10.1055/s-0040-1708019

  日期：2020.8

  Attempts to prepare azido-substituted aurones via a copper-catalyzed azidation failed to afford the desired product, but instead resulted in an unusual triazole formation reaction. Further efforts noted that copper was not required for this reaction, but simply thermal treatment with sodium azide in a polar aprotic solvent. A wide range of substitution patterns were tolerated in this reaction to afford

  试图通过铜催化的叠氮化制备叠氮基取代的金酮的尝试未能获得所需的产物，而是导致了异常的三唑形成反应。进一步的努力表明该反应不需要铜，而只需在极性非质子溶剂中简单地用叠氮化钠进行热处理即可。在该反应中容许各种各样的取代方式，以适中至优异的产率提供令人感兴趣的水杨基取代的三唑。尽管机理尚不清楚，但是考虑到相应硫代黄酮在反应上的失败，简单的消除/环化途径似乎不太可能，后者具有更好的硫醇离去基团。无论如何，这些易于获得的多功能化合物的潜在用途应引起更多的兴趣和应用。
• A Hg(OTf)₂-Catalyzed Enolate Umpolung Reaction Enables the Synthesis of Coumaran-3-ones and Indolin-3-ones
  作者：Zhouting Rong、Weican Hu、Ning Dai、Guoying Qian

  DOI：10.1021/acs.orglett.0c01096

  日期：2020.4.17

  The potential of mercury catalysis has been extended to the arena of enolate umpolung reactions for the first time by the generation of enolonium species via Hg(OTf)2-catalyzed N-oxide addition to alkynes. The enolonium species formed can undergo intramolecular nucleophilic attack by hydroxyl or amino groups, leading to the synthesis of various coumaran-3-ones and indolin-3-ones.

  汞催化的潜力已通过Hg（OTf）2催化的向炔烃中的N-氧化物加成生成en鎓物种，从而首次扩展到了烯醇式反应的领域。形成的enolonium物种可能会受到羟基或氨基的分子内亲核攻击，导致合成各种香豆素-3-酮和吲哚-3-酮。
• A copper iodide-catalyzed coupling reaction of benzofuran-3(2<i>H</i>)-ones with amines: an approach to α-ketoamides
  作者：Rongxiang Chen、Ruo-Ling Jia、Wenbo Li、Wei Zhao、Kai-Kai Wang、Zhan-Yong Wang、Xueji Ma、Wei Dai、Aili Sun

  DOI：10.1039/d1ob00715g

  日期：——

  A CuI-catalyzed coupling reaction of benzofuran-3(2H)-ones with amines has been well established for the direct synthesis of α-ketoamides. This process involves C–O bond cleavage and CO/C–N bond formation. Mechanism studies indicated that this α-ketoamide formation reaction may involve a free radical process.

  CuI 催化的 benzofuran-3( 2H )-ones 与胺的偶联反应已被很好地用于直接合成 α-酮酰胺。该过程涉及 C-O 键断裂和 C O/C-N 键形成。机理研究表明，这种α-酮酰胺形成反应可能涉及自由基过程。
• A golden opportunity: benzofuranone modifications of aurones and their influence on optical properties, toxicity, and potential as dyes
  作者：Joza Schmitt、Scott T Handy

  DOI：10.3762/bjoc.15.171

  日期：——

  Aurones are a small subclass of the flavonoid family known primarily for their unusual structure and the golden yellow color they impart to the flowers of snapdragons and cosmos. Most studies of aurones focus on their range of biological activities, but relatively little has been reported with respect to their optical properties, unlike their aza and thio analogs. What little is known has focused entirely

  金莲花是类黄酮家族的一个小亚类，主要因其不寻常的结构和赋予金鱼草和波斯菊花朵的金黄色而著称。大多数关于金光子的研究都集中在它们的生物活性范围上，但是与它们的氮杂和硫代类似物不同，关于其光学性质的报道相对较少。鲜为人知的完全集中在亚苄基部分的影响上。在这项研究中，研究了苯并呋喃酮环中取代基对UV-vis光谱的影响，并初步筛选了它们的毒性，并对它们作为织物染料的潜力进行了定性的初步研究。
• Simple alumina-mediated synthesis of 2-(2-hydroxypropan-2-yl)benzofuran-3(2 H )-ones
  作者：Lizhen Fang、Lili Han、Saisai Liu、Huanhuan Li

  DOI：10.1016/j.tetlet.2016.06.058

  日期：2016.7

  In this study, the Aldol condensation between benzofuran-3(2H)-ones and ketones or aldehydes mediated by alumina was developed. This simple protocol facilitated the synthesis of various 2-(2-hydroxypropan-2-yl)benzofuran-3(2H)-ones in moderate-to-high yields under mild conditions.

  在这项研究中，开发了苯并呋喃-3（2 H）-酮与氧化铝介导的酮或醛之间的醛醇缩合反应。这个简单的协议有助于在温和条件下以中等至高收率合成各种2-（2-羟基丙-2-基）苯并呋喃-3（2 H）-。