benzofuran-2-yl(4-fluorophenyl)methanone | 27044-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzofuran-2-yl(4-fluorophenyl)methanone
• 英文别名: 2-benzofuryl 4-fluorophenyl ketone；2-(p-fluorobenzoyl)benzofuran；benzofuran-2-yl-(4-fluoro-phenyl)-methanone；2-(p-Fluorobenzoyl)-benzofuran；Methanone, 2-benzofuranyl(4-fluorophenyl)-；1-benzofuran-2-yl-(4-fluorophenyl)methanone
• CAS: 27044-77-5
• 化学式: C₁₅H₉FO₂
• mdl: MFCD01618569
• 分子量: 240.234
• InChiKey: SFVGCTLMFVDKTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• 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：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  benzofuran-2-yl(4-fluorophenyl)methanone 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 98.0h， 生成 1-[1-Benzofuran-2-yl-(4-fluorophenyl)methyl]-1,2,4-triazole
  参考文献：
  名称：

  1-[（苯并呋喃-2-基）苯基甲基]-三唑和-四唑-芳香酶的有效竞争抑制剂。

  摘要：

  描述了一系列新的1-[（（苯并呋喃-2-基）苯基甲基]-三唑和-四唑的合成。使用[1β-3H]-雄烯二酮作为芳香酶的底物，体外测试了这些化合物对人胎盘芳香酶的抑制作用，其中包括抑制百分比和IC50数据。

  DOI：

  10.1016/s0960-894x(99)00328-5
• 作为产物：
  描述：

  苯并呋喃-2-羧酸 在 氯化亚砜 作用下， 生成 benzofuran-2-yl(4-fluorophenyl)methanone
  参考文献：
  名称：

  Synthesis and pharmacological study of new calcium antagonists, analogues of cinnarizine and flunarizine

  摘要：

  Several phosphonic diethyl esters were synthesized and their calcium antagonistic activity evaluated in vitro. The diethyl phosphonate group was condensed on substituted [diphenylmethyl], [(2-benzofuranyl)phenylmethyl], [(4-(diphenylmethyl-1 piperazinyl) methyl], [4-(4-diphenylmethyl-1-piperazinyl methyl) phenylmethyl], and [4-(3-phenyl-2-propenyl)-1-piperazinyl methyl] groups. Despite the presence of the diethyl phosphonate moiety and the benzhydrylpiperazinyl group, both present in potent calcium antagonist structures, only 1 of the 19 synthesized compounds exhibited a calcium antagonistic profile.

  DOI：

  10.1016/0223-5234(93)90049-k

文献信息

• 2,3-Diaroyl benzofurans from arynes: sequential synthesis of 2-aroyl benzofurans followed by benzoylation
  作者：Kashmiri Neog、Babulal Das、Pranjal Gogoi

  DOI：10.1039/c8ob00631h

  日期：——

  strategy for the direct synthesis of 2-aroyl benzofurans from aryne precursors has been developed. This reaction proceeds via C–O and C–C bond cleavage as well as C–O and C–C bond formation in a single reaction vessel. The methodology provides good yields of 2-aroyl benzofurans and tolerates a variety of functional groups. The synthesized 2-aroyl benzofurans were further benzoylated at 3-positions and

  已经开发了从芳烃前体直接合成2-芳酰基苯并呋喃的级联合成策略。该反应通过在单个反应容器中进行C–O和C–C键断裂以及C–O和C–C键形成而进行。该方法可提供2-芳酰基苯并呋喃的良好收率，并能耐受各种官能团。合成的2-芳酰基苯并呋喃在3-位进一步被苯甲酰化，并且合成的2，3-二酰酰基苯并呋喃结构之一通过X射线晶体学法得到明确证实。
• Ru-Catalyzed Branched versus Linear Selective C3-Alkylation of 2-Aroylbenzofurans with Acrylates via CH Activation
  作者：Yadagiri Kommagalla、Kolluru Srinivas、Chepuri V. Ramana

  DOI：10.1002/chem.201400401

  日期：2014.6.23

  carbonyl‐directed C3H activation and alkylation of 2‐aroylbenzo[b]furans with acrylates occurs selectively either in a linear or branched fashion, depending on the catalyst employed; [Ru(p‐cymene)Cl2]2 or Ru(PPh3)3Cl2, respectively. Two alternate pathways—funded upon the differences in steric and electronic preferences of these two complexes—is proposed for the selectivity of linear versus branched products.

  羰定向C3  ħ活化和2-芳酰基苯并[烷基化b ]呋喃与丙烯酸酯选择性地要么发生在直链或支链的方式，根据所用的催化剂; 分别为[Ru（p- cymene）Cl 2 ] 2或Ru（PPh 3）3 Cl 2。针对线性和支链产物的选择性，提出了两种替代途径（由这两种配合物的空间和电子偏好差异决定）。
• Facile preparation of aromatic ketones from aromatic bromides and arenes with aldehydes
  作者：Sousuke Ushijima、Souya Dohi、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1016/j.tet.2011.12.023

  日期：2012.2

  Aromatic ketones were efficiently prepared in good yields by the reactions of aryl bromides with n-BuLi, followed by the reactions with aromatic aldehydes or aliphatic aldehydes and the subsequent treatment with molecular iodine and K2CO3, in a one-pot method. The same treatment of arenes, instead of aromatic bromides, also provided the corresponding aromatic ketones in good yields. Using these methods

  通过一锅法，通过芳基溴化物与n- BuLi的反应，然后与芳族醛或脂族醛的反应，以及随后用分子碘和K 2 CO 3的处理，可以有效地以高收率高效地制备芳族酮。芳烃的相同处理而不是芳族溴化物也以良好的产率提供了相应的芳族酮。使用这些方法，可以通过简单，无过渡金属且因此对环境无害的实验程序有效地制备各种带有富电子芳族化合物和缺电子芳族化合物的二芳基酮和烷基芳基酮。
• Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles
  作者：Julin Gong、Kun Hu、Yinlin Shao、Renhao Li、Yetong Zhang、Maolin Hu、Jiuxi Chen

  DOI：10.1039/c9ob02408e

  日期：——

  example of the palladium-catalyzed tandem addition/cyclization of 2-(2-acylphenoxy)acetonitriles with arylboronic acids has been developed, providing a new strategy for the synthesis of 2-aroyl benzofurans with excellent chemoselectivity and wide functional group compatibility. Preliminary mechanistic experiments indicate that this tandem process involves sequential nucleophilic addition generating 2

  已经开发了钯催化串联2-（2-酰基苯氧基）乙腈与芳基硼酸的串联/加成反应的第一个实例，为合成具有优异的化学选择性和广泛的官能团相容性的2-芳酰基苯并呋喃提供了新的策略。初步的机理实验表明，该串联过程涉及顺序的亲核加成，产生2-（2-酰基苯氧基）-1-苯基乙-1-酮，然后进行分子内环化。该方法也已用于2-芳酰基吲哚和强效CYP19抑制剂1-（苯并呋喃-2-基（苯基）甲基）-1H-1,2,4-三唑的合成。
• Syntheses of 2-Aroyl Benzofurans through Cascade Annulation on Arynes
  作者：Pashikanti Gouthami、Lahu N. Chavan、Rambabu Chegondi、Srivari Chandrasekhar

  DOI：10.1021/acs.joc.8b00360

  日期：2018.3.16

  The highly efficient and expedient route for the syntheses of 2-aroyl benzofurans has been developed via the cascade [2+2] followed by a [4+1] annulation on arynes. The overall transformation proceeded through the formation of ortho-quinone methide by the insertion of transient aryne into N,N-dimethylformamide and subsequent trapping with sulfur ylide. Moreover, this transformation has a broad range

  通过级联[2 + 2]，然后在芳烃上进行[4 + 1]环化，已经开发出了2-芳酰基苯并呋喃的高效合成途径。通过将瞬时的芳烃插入N，N-二甲基甲酰胺中，然后用硫内鎓盐捕集，通过形成邻醌甲基化物来进行整体转化。而且，该转变具有高官能团耐受性的广泛的基板范围。该新反应已成功用于有效的CYP19芳香酶抑制剂的合成和对生物活性复合物雌酮的后期功能化。