[2-(4-甲氧基苯基)-1-苯并呋喃-3-基](4-甲氧基苯基)甲酮 | 102593-72-6

• 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
• 中文名称: [2-(4-甲氧基苯基)-1-苯并呋喃-3-基](4-甲氧基苯基)甲酮
• 英文名称: <2-(4-methoxyphenyl)-1-benzofuran-3-yl>(4-methoxyphenyl)methanone
• 英文别名: 3-(4’-methoxybenzoyl)-2-(4’-methoxyphenyl)benzofuran；2-<4-Methoxy-phenyl>-3-<4-methoxy-benzoyl>-cumaron；(4-methoxy-phenyl)-[2-(4-methoxy-phenyl)-benzofuran-3-yl]-methanone；(4-Methoxyphenyl)-[2-(4-methoxyphenyl)-1-benzofuran-3-yl]methanone
• CAS: 102593-72-6
• 化学式: C₂₃H₁₈O₄
• 分子量: 358.394
• InChiKey: TVKSCNIHILDMGO-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C
• 沸点：
  560.9±50.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-(4-甲氧基苯基)-1-苯并呋喃-3-基](4-甲氧基苯基)甲酮 在 吡啶盐酸盐 作用下， 反应 2.0h， 生成 (4-羟基苯基)-[2-(4-羟基苯基)-1-苯并呋喃-3-基]甲酮
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. A study using triarylbutenone, benzofuran, and triarylfuran analogs as models for triarylethylenes and triarylpropenones

  摘要：

  In a study of the structure-activity relationship (SAR) of antiestrogens use has been made of certain 1,2,3-triarylbutenones, of 2-arylbenzofurans carrying aryl or aroyl substituents at C3, and of 2,3,4-triarylfurans as conformationally constrained models for triarylethylene (TAE) and triarylpropenone (TAP) prototypes. The position-specific contributions of substituents to receptor affinity and to agonist-antagonist profiles were used as aids in characterizing the relative binding orientation of the prototypes. Although most compounds were found to be weak receptor ligands and poorly active in vivo, the following conclusions could be drawn about their SAR: (i) (Z)-TAPs and TAEs interact with the receptor in an analogous manner using the trans-stilbene core, with their agonist-antagonist profiles depending on the nature of other substructures. (ii) Incorporation into the benzofuran framework introduces a stereoelectronic constraint that compromises the normal binding interactions of TAE, as well as TAP, prototypes, resulting in their poor affinities and weak biological activities. (iii) (E)-TAPs can interact with the receptor through their S-cis conformation, but such a binding mode is unlikely to account for their behavior as antagonists.

  DOI：

  10.1021/jm00128a006
• 作为产物：
  描述：

  在 bis(1,5-cyclooctadiene)nickel (0) 、 C₂₃H₃₂N₂*H⁽¹⁺⁾*BF₄^(1-) 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以88%的产率得到[2-(4-甲氧基苯基)-1-苯并呋喃-3-基](4-甲氧基苯基)甲酮
  参考文献：
  名称：

  邻炔基苯酚酯的镍催化酰基转移与C-O键裂变的合成苯并[b]呋喃

  摘要：

  在此，我们报道了邻炔基苯基酯的镍催化级联C-O键裂解/环化反应，以构建3-酰基苯并[ b ]呋喃骨架。反应条件筛选的结果是，发现Ni（0）/ IAd（1,3-Di（1-金刚烷基）咪唑-2-亚基）体系最适合催化转化。有趣的是，该反应仅生成3-酰基苯并[ b用呋喃代替在羰基镍物种介导的反应中经常观察到的脱羰基产物。催化剂的负载量可以降低到5-10 mol％。我们证明了各种功能化的3酰基苯并呋喃衍生物的合成。我们进行了镍配合物的化学计量研究以及密度泛函理论（DFT）计算，以支持可能的反应机理。

  DOI：

  10.1002/cctc.202001949

文献信息

• Significant Enhancement in the Efficiency and Selectivity of Iron-Catalyzed Oxidative Cross-Coupling of Phenols by Fluoroalcohols
  作者：Eden Gaster、Yulia Vainer、Almog Regev、Sachin Narute、Kavitha Sudheendran、Aviya Werbeloff、Hadas Shalit、Doron Pappo

  DOI：10.1002/anie.201409694

  日期：2015.3.27

  Significant enhancement of both the rate and the chemoselectivity of iron‐catalyzed oxidative coupling of phenols can be achieved in fluorinated solvents, such as 1,1,1,3,3,3‐hexafluoropropan‐2‐ol (HFIP), 2,2,2‐trifluoroethanol (TFE), and 1‐phenyl‐2,2,2‐trifluoroethanol. The generality of this effect was examined for the cross‐coupling of phenols with arenes and polycyclic aromatic hydrocarbons (PAHs)

  在氟化溶剂（例如1,1,1,3,3,3-六氟丙烷-2-醇（HFIP），2,2）中，可以显着提高苯酚的铁催化氧化偶联的速率和化学选择性。 ，2-三氟乙醇（TFE）和1-苯基-2-2,2,2-三氟乙醇。考察了苯酚与芳烃和多环芳烃（PAHs）以及苯酚与β-二羰基化合物的交叉偶联的普遍性。新的条件仅在四个合成步骤中就用于合成2'''-dehydroxycalodeninB。
• Unexpected one-step synthesis of 3-benzoyl-2-phenylbenzofurans under Wittig conditions
  作者：Michela Begala、Pierluigi Caboni、Maria João Matos、Giovanna Lucia Delogu

  DOI：10.1016/j.tetlet.2018.03.048

  日期：2018.5

  conditions, led to 2-phenylbenzofuran derivatives 4a–p and the unexpected formation of 3-benzoyl-2-phenylbenzofuran derivatives 5a–p. Benzoyl chlorides possessing electron-withdrawing groups afforded 3-benzoyl-2-phenylbenzofuran derivatives in higher yields than those with electron-donating groups. This reaction represents a simple and regioselective, one-pot route towards the preparation of deactivated

  在Wittig条件下，2-羟基苄基三苯基溴化with与取代的苯甲酰氯反应，生成2-苯基苯并呋喃衍生物4a - p以及意外地形成了3-苯甲酰基-2-苯基苯并呋喃衍生物5a - p。具有吸电子基团的苯甲酰氯以比具有给电子基团的苯甲酰氯更高的产率得到3-苯甲酰基-2-苯基苯并呋喃衍生物。该反应代表了制备失活的3-苯甲酰基-2-苯基苯并呋喃化合物的简单且区域选择性的一锅法，这是很难通过直接将2-苯基苯并呋喃酰化而获得的。
• Unexpected detection of 3-aroylbenzofuran side products in the preparation of 2-arylbenzofurans: Identification, characterization, and comparison with chalcone's fragmentation patterns using EI/MSⁿ
  作者：Michela Begala、Giovanna Lucia Delogu

  DOI：10.1002/jms.4425

  日期：2019.9

  ran, on the base of its mass spectrometric behaviour using a combination of electron ionization, exact mass measurement, multiple stage mass spectrometry, and labelled compounds. This study reports the common fragmentation pathways and discusses possible fragment structures of characteristic ions from a series of 3-aroyl-2-arylbenzofuran derivatives obtained as by-product under Wittig conditions. Emphasis

  分子内维蒂希反应的气相色谱-质谱研究表明，与预期的2-苯基苯并呋喃一起，形成了迄今为止尚未报道的意外副产物。这项研究报告了结合电子电离，精确质量测量，多级质谱和标记化合物的质谱行为，从而鉴定了副产物3-苯甲酰基-2-苯基苯并呋喃。这项研究报告了常见的碎片化途径，并讨论了在维蒂希条件下从副产品中获得的一系列3-芳基-2-芳基苯并呋喃衍生物的特征离子的可能碎片结构。重点放在[MH] +和[M-OH] +离子的形成和结构研究上。
• DURANI, NEELAM;JAIN, RAKA;SAEED, ASHRAF;DIKSHIT, DINESH K.;DURANI, SUSHEE+, J. MED. CHEM., 32,(1989) N, C. 1700-1707
  作者：DURANI, NEELAM、JAIN, RAKA、SAEED, ASHRAF、DIKSHIT, DINESH K.、DURANI, SUSHEE+

  DOI：——

  日期：——