(Z)-2-benzylidene-5-chlorobenzofuran-3(2H)-one | 3261-08-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-2-benzylidene-5-chlorobenzofuran-3(2H)-one
• 英文别名: (2Z)-2-benzylidene-5-chloro-benzofuran-3-one；(2Z)-2-benzylidene-5-chloro-1-benzofuran-3-one
• CAS: 3261-08-3
• 化学式: C₁₅H₉ClO₂
• 分子量: 256.688
• InChiKey: CPBANXAQQGJCHB-ZSOIEALJSA-N

物化性质

• 沸点：
  426.3±45.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2'-acetoxy-5'-chlorochalcone 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 为溶剂， 反应 73.0h， 生成 (Z)-2-benzylidene-5-chlorobenzofuran-3(2H)-one
  参考文献：
  名称：

  惠勒黄酮合成中的黄酮形成

  摘要：

  发现当被氢氧化乙醇水溶液环化时，通过2'-乙酰氧基查耳酮的侧链的溴甲基化形成的二氢查耳酮产生少量的黄酮以及主要的产品金酮。黄酮类化合物的产率随碱浓度的增加而增加。用于形成金酮的氢氧化物的最佳浓度低于1％。当在环化2'-氧官能团的对面引入硝基取代基时，会大大降低O-杂环的收率。

  DOI：

  10.1016/s0040-4020(01)87902-3

文献信息

• An Efficient Synthesis of Aurone Derivatives by the Tributylphosphine-catalyzed Regioselective Cyclization of <i>o</i>-Alkynoylphenols
  作者：Koya Saito、Masahito Yoshida、Takayuki Doi

  DOI：10.1246/cl.140910

  日期：2015.2.5

  An organocatalytic regioselective synthesis of aurones from o-alkynoylphenols was achieved. A catalytic amount of tributylphosphine selectively induced the 5-exo cyclization of o-alkynoylphenols under ambient conditions leading to aurone derivatives in high to excellent yields.

  实现了从o-烷炔酰基苯酚的有机催化区选择性合成黄烷酮的方法。少量的三丁基膦在常温下选择性诱导o-烷炔酰基苯酚的5-exo环化，产生黄烷酮衍生物，收率高至优异。
• One-pot Synthesis of Aurones through Oxidation-cyclization Tandem Reaction Catalyzed by Copper Nanoparticles Catalyst
  作者：Min Yu、Guangxiang Liu、Chengyan Han、Li Zhu、Xiaoquan Yao

  DOI：10.2174/1570178614666171110150853

  日期：2017.12.11

  Aurones were synthesized through an oxidation-cyclization tandem reaction of 2-(1- hydroxyprop-2-ynyl)phenols catalyzed by copper nanoparticles (Cu NPs) with bipyridine as the ligand. In the reaction, oxygen worked as a green and mild oxidant to give the best results. Cu NPs were dually activated by bipyridine ligand and water, and showed highly efficient catalytic activities to the oxygen oxidation

  通过以联吡啶为配体的铜纳米粒子（Cu NPs）催化的2-（1-羟基丙-2-炔基）苯酚的氧化环化串联反应合成了金酮。在反应中，氧气起绿色和中度氧化剂的作用，以达到最佳效果。Cu NP被联吡啶配体和水双重激活，对氧的氧化和环化反应显示出高效的催化活性，从而生成金酮和类黄酮。
• Water-Promoted, Silver–Phosphine Complex–Catalyzed Stereoselective Cyclization of 2-(1-Hydroxy-3-arylprop-2-ynyl)phenols Leading to a Highly Efficient Approach to Aurones
  作者：Mingdeng Lin、Min Yu、Chengyan Han、Chao-Jun Li、Xiaoquan Yao

  DOI：10.1080/00397911.2010.517613

  日期：2011.11.1

  Silver-phosphine complexes can be utilized as highly efficient catalysts for the cyclization of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols (1) to give product 2, key intermediates to synthesize aurones (4), with good yields and stereoselectivities in water-toluene mixed solvent. With fluoride as the counteranion, complete E- or Z-stereoselectivities were achieved at high temperature or room temperature, respectively. Furthermore, after removing water from the reaction mixtures, the toluene solution containing crude products 2 can be treated by MnO2 directly without further purification, to give aurones 4 in good yields.
• Shah; Parikh, Journal of the Indian Chemical Society, 1959, vol. 36, p. 726
  作者：Shah、Parikh

  DOI：——

  日期：——
• Synthesis of Aurones through Silver-catalyzed Intramolecular Cyclization from <i>o</i> -Alkynonylphenols
  作者：Woonsang Hwang、Hyunseok Kim、Hyuck Choi、Jaehyun Kim、Woo Hyung Jeon、Phil Ho Lee、Kooyeon Lee

  DOI：10.1002/bkcs.11384

  日期：2018.3