2-(p-tolyl)benzofuran-5-ol | 1193359-90-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-(p-tolyl)benzofuran-5-ol
• 英文别名: 5-hydroxy-2-(4-methylphenyl)benzofuran；2-(4-Methylphenyl)-1-benzofuran-5-ol
• CAS: 1193359-90-8
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: BHOBRODVARLUOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-hydroxy-4-(p-tolylethynyl)cyclohexa-2,5-dienone 在 platinum(II) chloride 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 以80%的产率得到2-(p-tolyl)benzofuran-5-ol
  参考文献：
  名称：

  A Direct Approach to 5-Hydroxybenzofurans via a Platinum-Catalyzed Domino Rearrangement/5-endo-dig Cyclization Reaction of Quinols

  摘要：

  A highly efficient and atom-economical construction of 2-substituted 5-hydroxybenzofurans was accomplished by employing a platinum-catalyzed domino dienone-phenol rearrangement/5-endo-dig cyclization reaction of quinols bearing alkynes.

  DOI：

  10.1021/jo901937u

文献信息

• Synthesis of Benzofurans from Ketones and 1,4-Benzoquinones
  作者：Fengtian Wu、Rongxian Bai、Yanlong Gu

  DOI：10.1002/adsc.201600048

  日期：2016.7.14

  Benzofuran derivatives can be synthesized through the sequential Michael addition and cyclization of 1,3‐dicarbonyl compounds with 1,4‐benzoquinones. However, ketones are rarely used in this reaction because of their low nucleophilicities. In this study, this problem was solved by utilizing triethyl orthoformate, which enabled the formation of a vinyl ethyl ether as an additive. As a result, the nucleophilicity

  苯并呋喃衍生物可以通过依次进行迈克尔加成反应和将1,3-二羰基化合物与1,4-苯醌合成的方法合成。但是，由于其亲核性低，因此在该反应中很少使用酮。在这项研究中，通过使用原甲酸三乙酯解决了这个问题，这使得能够形成乙烯基乙基醚作为添加剂。结果，酮的亲核性增加。通过这些新近建立的反应，还制备了许多重要的5-羟基苯并呋喃衍生物，这些衍生物过去很难通过合成获得。
• Isotopically-Labeled Benzofuran Compounds as Imaging Agents for Amyloidogenic Proteins
  申请人：Klunk William E.

  公开号：US20080274058A1

  公开（公告）日：2008-11-06

  Benzofuran compounds which contain at least one detectable label selected from the group consisting of 131 I, 123 I, 124 I, 125 I, 76 Br, 75 Br, 18 F, 19 F, 11 C, 13 C, 14 C and 3 H are provided as amyloid imaging agents for detecting brain amyloid deposits as well as other amyloidogenic peptides associated with systemic or localized amyloidosis. Additionally, the compounds are useful for determining if patients, presenting with clinically confusing cases of dementia or presenting with mild cognitive impairment, have Alzheimer's disease. The compounds are additionally useful as surrogate markers for monitoring the efficacy of anti-amyloidosis therapies.

  提供了含有至少一种可检测标记的苯并呋喃类化合物，所述可检测标记选自131I、123I、124I、125I、76Br、75Br、18F、19F、11C、13C、14C和3H，作为淀粉样蛋白成像剂，用于检测脑淀粉样沉积物以及与全身或局部淀粉样变性相关的其他淀粉样肽。此外，这些化合物可用于确定患有临床混淆的痴呆症状或轻度认知障碍的患者是否患有阿尔茨海默病。这些化合物还可用作监测抗淀粉样变性治疗疗效的代用标记。
• US8138360B2
  申请人：——

  公开号：US8138360B2

  公开（公告）日：2012-03-20
• A Direct Approach to 5-Hydroxybenzofurans via a Platinum-Catalyzed Domino Rearrangement/5-<i>endo</i>-<i>dig</i> Cyclization Reaction of Quinols
  作者：Ikyon Kim、Kyungsun Kim、Jungeun Choi

  DOI：10.1021/jo901937u

  日期：2009.11.6

  A highly efficient and atom-economical construction of 2-substituted 5-hydroxybenzofurans was accomplished by employing a platinum-catalyzed domino dienone-phenol rearrangement/5-endo-dig cyclization reaction of quinols bearing alkynes.