1,3-diphenyl-3H-benzo[f]chromene | 117922-01-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 1,3-diphenyl-3H-benzo[f]chromene
• 英文别名: 4,6-Diphenyl-6H-naphtho<2',1':2,3>pyran
• CAS: 117922-01-7
• 化学式: C₂₅H₁₈O
• 分子量: 334.417
• InChiKey: BQTYKEONKOAQNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(1,3-diphenylprop-2-ynyl)naphthalen-2-ol 在 iron(III) chloride 、 苯胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以50%的产率得到1,3-diphenyl-3H-benzo[f]chromene
  参考文献：
  名称：

  铁催化的CC三键区域选择性氢芳氧基化：2 H -1-苯并吡喃衍生物的有效合成。

  摘要：

  报道了2-炔丙基酚或萘酚的有效的，区域选择性的，铁催化的分子内氢芳氧基化。反应通过内挖法环化进行，以氯化铁（III）为催化剂，在二甲基甲酰胺（DMF）中苯胺的辅助下，以高至高收率获得苯并吡喃或萘并吡喃衍生物。

  DOI：

  10.1002/adsc.200900483

文献信息

• Gallium(III) chloride-catalyzed three-component coupling of naphthol, alkyne and aldehyde: a novel synthesis of 1,3-disubstituted-3H-benzo[f] chromenes
  作者：J.S. Yadav、B.V. Subba Reddy、Swapan Kumar Biswas、Sandip Sengupta

  DOI：10.1016/j.tetlet.2009.07.134

  日期：2009.10

  Three-component coupling of naphthol, alkyne and aldehyde has been achieved in the presence of 10 mol % gallium(III) chloride in toluene under reflux conditions to afford the corresponding 1,3-disubstituted-3H-benzo[f]chromenes in good yields. This is the first example on the preparation of chromenes from naphthol, alkyne and aldehyde.

  在甲苯中存在10 mol％氯化镓（III）的条件下，在回流条件下，萘酚，炔烃和醛的三组分偶联反应得以实现，从而得到相应的1,3-二取代-3 H-苯并[ f ]色烯。产量。这是从萘酚，炔烃和醛制备二苯甲基苯的第一个实例。
• Ultrasound-assisted one-pot synthesis of disubstituted and trisubstituted 1H-benzo[f]chromene derivatives catalyzed by 4-nitro-2,6-diacetylpyridinebis(2,4,6-trimethylaniline)FeCl2
  作者：Reza Sandaroos、Saman Damavandi

  DOI：10.1007/s11164-012-0933-y

  日期：2013.11

  1,3-Diaryl-1H-benzo[f]chromenes and 1,3-diaryl-1H-benzo[f]chromen-2-yl)(phenyl)methanones have been synthesized by one-pot three-component reaction of naphthols, aromatic aldehydes, and acetophenone or 1,3-diphenylpropane-1,3-dione, with the bis(imino)pyridine iron-based catalyst 4-nitro-2,6-diacetylpyridinebis(2,4,6-trimethylaniline)FeCl2. This novel, efficient, and rapid method is performed under solvent-free conditions with ultrasonic irradiation.

  1,3-二芳基-1H-苯并[f]苯并吡喃和1,3-二芳基-1H-苯并[f]苯并吡喃-2-基)(苯基)甲酮是通过萘酚、芳香醛和苯乙酮或1,3-二苯基丙烷-1,3-二酮与双(亚氨基)吡啶铁基催化剂4-硝基-2,6-二乙酰基吡啶双(2,4,6-三甲基苯胺)FeCl2的一锅三组分反应合成的。这种新颖、高效、快速的方法在无溶剂条件下进行超声波照射。
• Propargylation of Aromatic Compounds with Propargylic Alcohols Catalyzed by a Cationic Diruthenium Complex
  作者：Yoshiaki Nishibayashi、Youichi Inada、Masato Yoshikawa、Masanobu Hidai、Sakae Uemura

  DOI：10.1002/anie.200250532

  日期：2003.4.4
• Efficient one-pot synthesis of 1,3-diaryl-3H-benzo[f]chromenes using ferric hydrogensulfate
  作者：Hossein Eshghi、Gholam Hossein Zohuri、Saman Damavandi、Mohammad Vakili

  DOI：10.1016/j.cclet.2010.07.007

  日期：2010.12

  An efficient and easy method for one-pot three-component synthesis of 1,3-disubstituted-3H-benzo[f]chromenes by the condensation of naphtol, aromatic aldehyde derivatives and phenylacetylene in the presence of ferric hydrogensulfate [Fe(HSO4)(3)], has been described. The catalyst displayed high activity which afforded the corresponding 1,3-disubstituted-3H-benzo[f]chromenes in satisfying yields. Alkyl-substituted phenols were examined and the corresponding benzopyran derivatives were synthesized in moderate yields. Heterogeneous nature of the using catalyst made it reusable for further chemical reactions. (C) 2010 Hossein Eshghi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.