(3,5-diphenyl-2-furyl)(phenyl)methanone | 57314-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: (3,5-diphenyl-2-furyl)(phenyl)methanone
• 英文别名: 2-Benzoyl-3,5-diphenylfuran；(3,5-diphenylfuran-2-yl)-phenylmethanone
• CAS: 57314-28-0
• 化学式: C₂₃H₁₆O₂
• 分子量: 324.379
• InChiKey: WARDLFLSFXYNRO-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C(Solv: ethanol (64-17-5))
• 沸点：
  539.5±50.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3,5-diphenyl-2-furyl)(phenyl)methanone 在 potassium tert-butylate 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 2,4-diphenylfuran
  参考文献：
  名称：

  A Convenient Regioselective Synthesis of 2,4-Diarylfurans

  摘要：

  本文介绍了一种在温和条件下以苯甲醛和苯乙酮为起点，采用哈勒-鲍尔型裂解 2-芳酰基-3,5-二芳基呋喃的方法，合成两个芳基环上具有相同或不同取代基的 2,4-二芳基呋喃的简便三步法。

  DOI：

  10.1055/s-1999-3668
• 作为产物：
  描述：

  2,4,6-triphenyl-4H-pyran 在 lead(IV) acetate 作用下， 以 苯 为溶剂， 反应 3.83h， 以58%的产率得到(3,5-diphenyl-2-furyl)(phenyl)methanone
  参考文献：
  名称：

  Drevko, B. I.; Smushkin, M. I.; Kharchenko, V. G., Russian Journal of Organic Chemistry, 1995, vol. 31, # 9, p. 1298 - 1299

  摘要：

  DOI：

文献信息

• Inhibitors of P2X3
  申请人：Brotherton-Pleiss E. Christine

  公开号：US20070037974A1

  公开（公告）日：2007-02-15

  Compounds of formula 1 are modulators of P2X3 useful for the treatment of pain and genito-urinary, gastrointestinal, and respiratory disorders: wherein R 1 is —C(═S)CH 3 , pyridyl, pyrimidinyl, pyrazinyl, thiazolyl, furyl, furylcarbonyl, acetyl, or carbamoyl; R 2a and R 2b are independently H, methyl, or ethyl; R 3 is H or methyl; Y is a bond, —(CR 4 R 5 ) n — or —CR 4 ═CR 5 —; wherein R 4 and R 5 are each independently H or methyl and n is 1 or 2; X is N or CH; A is phenyl, 5-membered heterocyclyl, or 6-membered heterocyclyl; R 6 , R 7 and R 8 are each independently H, halo, lower alkyl, cycloalkyl, alkylthio, alkylthio-lower alkyl, alkylsulfonyl-lower alkyl, di(lower alkyl)amino-lower alkyl, morpholinyl-lower alkyl, 4-methyl-piperazinyl-methyl, trifluoromethyl, pyridyl, tetrazolyl, thiophenyl, phenyl, biphenyl, or benzyl (where thiophenyl, phenyl and benzyl are substituted with 0-3 lower alkyl, halo, sulfonamido, trifluoromethyl, lower alkoxy or lower alkylthio) or R 6 and R 7 together form a 5-membered or 6-membered carbocyclic or heterocyclic ring substituted with 0-3 substituents selected from the group consisting of lower alkyl, lower alkoxy, oxo, halo, thiophenyl-lower alkyl, phenyl, benzyl (where phenyl and benzyl are substituted with 0-3 lower alkyl, halo, sulfonamido, trifluoro-methyl, lower alkoxy, lower alkylthio, amino-lower alkyl, lower alkylamino-lower alkyl, or di(lower alkyl)amino-lower alkyl); and pharmaceutically acceptable salts thereof; wherein when R 1 is pyrimidin-2-yl, X is N, Y is a bond and A is oxazol-5-yl the carbon atom at position 4 in said oxazol-5-yl is not substituted by propyl when the carbon atom at position 2 in said oxazol-5-yl is substituted by substituted phenyl and the carbon atom at position 4 in said oxazol-5-yl is not substituted by phenyl when the carbon atom at position 2 is substituted by unsubstituted or substituted phenyl.

  式1的化合物是P2X3的调节剂，用于治疗疼痛和泌尿生殖、胃肠和呼吸系统疾病： 其中 R 1 为—C(═S)CH 3 ，吡啶基，嘧啶基，吡嗪基，噻唑基，呋喃基，呋喃甲酰基，乙酰基或氨基甲酰基；R 2a 和R 2b 独立地为H，甲基或乙基；R 3 为H或甲基；Y为键，—(CR 4 R 5 ) n —或—CR 4 ═CR 5 —；其中R 4 和R 5 各自独立地为H或甲基，n为1或2；X为N或CH；A为苯基，5-成员杂环基或6-成员杂环基；R 6 ，R 7 和R 8 各自独立地为H，卤素，低碳基，环烷基，烷基硫醚，烷基硫醚-低碳基，烷基磺酰基-低碳基，二(低碳基)氨基-低碳基，吗啉基-低碳基，4-甲基哌嗪基-甲基，三氟甲基，吡啶基，四唑基，噻吩基，苯基，联苯基或苄基（其中噻吩基，苯基和苄基被0-3个低碳基，卤素，磺酰胺基，三氟甲基，低烷氧基或低烷硫基取代）或R 6 和R 7 一起形成一个被0-3个取自由低碳基，低烷氧基，氧代基，卤素，噻吩基-低碳基，苯基，苄基（其中苯基和苄基被0-3个低碳基，卤素，磺酰胺基，三氟甲基，低烷氧基，低烷硫基，氨基-低碳基，烷基氨基-低碳基或二(低碳基)氨基-低碳基取代）的5-成员或6-成员碳环或杂环取代环；及其药学上可接受的盐；其中当R 1 为嘧啶-2-基时，X为N，Y为键，A为噁唑-5-基时，所述噁唑-5-基中位置4的碳原子在所述噁唑-5-基中位置2的碳原子被取代的苯基取代时不被丙基取代，且所述噁唑-5-基中位置4的碳原子在位置2被取代的苯基取代时不被苯基取代。
• Gold(I)-Catalyzed and H₂O-Mediated Carbene Cascade Reaction of Propargyl Diazoacetates: Furan Synthesis and Mechanistic Insights
  作者：Ming Bao、Yu Qian、Han Su、Bing Wu、Lihua Qiu、Wenhao Hu、Xinfang Xu

  DOI：10.1021/acs.orglett.8b02251

  日期：2018.9.7

  A novel gold-catalyzed water-mediated carbene cascade reaction of propargyl diazoacetates has been developed. Mechanistic investigation indicates that this reaction is initiated by gold-catalyzed gold–carbene formation followed by an unprecedented 6-endo-dig carbocyclization with tethered alkyne through an oxonium ylide intermediate, terminated by a β-H elimination/protodeauration process to give the

  已开发出一种新型的金催化的炔丙基重氮乙酸酯水介导的卡宾级联反应。机理研究表明，该反应是由金催化的金卡宾的形成引发的，然后是空前的6-内消旋碳环化，通过氧代叶立德中间体与束缚的炔烃结合，然后被β-H消除/原脱氮过程终止，得到芳构化的呋喃产品具有良好的高收率和广泛的基材通用性。值得注意的是，拟议的金卡宾中间体已通过拦截实验得到了验证。
• An eco-benign and high speed protocol for the synthesis of 2-aroyl-3,5-diarylfuran derivatives using Teflon-supported iodine
  作者：Arash Mouradzadegun、Mohammad Reza Ganjali、Fatemeh Abadast、Fatemeh Rahimi

  DOI：10.1007/s00706-017-2061-2

  日期：2018.1

  AbstractA new, practical, and convenient approach has been established for the expeditious synthesis of bioactive 2-aroyl-3,5-diarylfurans in excellent yields using a iodine-impregnated Teflon by a microwave-promoted process. The products are isolated without tedious aqueous work-up in high purity. The microwave accelerated the reaction and renders the whole synthesis into a truly eco-friendly protocol

  摘要已经建立了一种新的，实用且方便的方法，该方法可通过碘促进的聚四氟乙烯，通过微波促进的方法，以优异的产率快速合成生物活性的2-芳酰基-3,5-二芳基呋喃。分离出的产物无需繁琐的高纯度后处理。微波加速了反应，并使整个合成过程成为真正的环保方案。 图形概要 。
• Synthesis of 2-aroylfuran and novel 3,5-diaroyl-4-arylisoxazole derivatives by ring contraction of pyrylium salts
  作者：Arash Mouradzadegun、Fatemeh Abadast、Somayeh Elahi、Neda Askarikia

  DOI：10.1007/s11164-015-2202-3

  日期：2016.4

  Abstract Ring contraction of 2,4,6-triarylpyrylium perchlorates by use of sodium nitrite mediated by ionic liquid has been used as a new, direct, and environmentally benign method for synthesis of bioactive 2-aroylfuran and novel 3,5-diaroyl-4-arylisoxazole derivatives in excellent yields. The versatility of the approach enables rapid and simple access to these pharmaceutically important compounds

  摘要 离子液体介导的亚硝酸钠对高氯酸2,4,6-三芳基吡啶鎓的环收缩反应已被用作合成生物活性2-芳酰基呋喃和新颖的3,5-二芳酰基-4的直接，环境友好的新方法。 -芳基异恶唑衍生物，收率优异。该方法的多功能性使得能够快速简便地获得这些药学上重要的化合物。通过简单过滤容易地从反应混合物中分离出产物。 图形概要
• Free radicals: XXVIII. Reaction of 2,4,6-triphenylpyranyl with (diacetoxy-λ3-iodanyl)benzene
  作者：B. S. Tanaseichuk、M. K. Pryanichnikova、A. A. Burtasov、A. I. Lisina、A. V. Dolganov

  DOI：10.1134/s1070428011030201

  日期：2011.3

  The major product of the reaction of 2,4,6-triphenylpyranyl with (diacetoxy-lambda(3)-iodanyl) benzene in acetonitrile and acetone was 2,4,6-triphenylpyrylium acetate. Analogous reaction in isopropyl alcohol resulted in the formation of methane, carbon dioxide, 1,3,5-triphenylpent-2-ene-1,5-dione, 2-benzoyl-3,5-diphenylfuran, 1,3,5-triphenylpenta-2,4-dien-1-one, and a small amount of 2,4,6-triphenylpyrilium acetate.