6-methyl-2,3-diphenyl-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 6-methyl-2,3-diphenyl-4H-chromen-4-one
• 英文别名: 6-Methyl-2,3-diphenylchromen-4-one
• 化学式: C₂₂H₁₆O₂
• 分子量: 312.368
• InChiKey: SAOHXSVWSKPTKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methyl-2,3-diphenyl-4H-chromen-4-one 以 乙醇 、 水 为溶剂， 反应 3.0h， 以62%的产率得到12-methyl-14H-dibenzo[a,c]xanthen-14-one
  参考文献：
  名称：

  的环2,3-二苯基-4- ħ -苯并吡喃-4-酮通过光诱导的析氢†

  摘要：

  描述了一种在室温下在EtOH–H 2 O（19：1，v / v）中有效的无光诱导的无过渡金属的直接氢释放和2,3-二苯基-4 H-铬4-4-酮的环化反应。。所报道的方法提供了快速简便地合成二苯并[ a，c ]黄嘌呤衍生物的方法，从而无需使用任何催化剂，氧化剂和添加剂。

  DOI：

  10.1039/c7ra09770k
• 作为产物：
  描述：

  苯乙酸对甲酚酯 在 aluminum (III) chloride 、 5%-palladium/activated carbon 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 氯苯 为溶剂， 反应 12.0h， 生成 6-methyl-2,3-diphenyl-4H-chromen-4-one
  参考文献：
  名称：

  通过远程消除氢化物实现C–H功能化：钯催化邻酰基苯酚脱氢为类黄酮

  摘要：

  尽管人们早就知道贫电子的C–H键与碱形成碳阴离子的去质子化并广泛用于有机合成中，但从富电子的C–H键与碳阳离子或部分碳阳离子的氢化物消除是引入亲核试剂的一个重要方法。勘探面积相对较少。在这里，我们报道邻酰基苯酚的羰基β-C（sp 3）–H键氢可被分子内酚羟基取代形成O杂环，然后将O杂环脱氢成类黄酮。在不添加氧化剂和不牺牲氢受体的情况下，Pd / C催化级联反应。

  DOI：

  10.1021/acs.orglett.6b03652

文献信息

• Iridium-Catalyzed and Ligand-Controlled Carbonylative Synthesis of Flavones from Simple Phenols and Internal Alkynes
  作者：Fengxiang Zhu、Zechao Wang、Yahui Li、Xiao-Feng Wu

  DOI：10.1002/chem.201700233

  日期：2017.3.8

  Flavones are important natural products with diverse biological activities. In this study, a novel procedure for the carbonylative synthesis of flavones has been developed by using simple phenols and internal alkynes as the substrates. Various flavones were isolated in moderate to good yields with excellent regioselectivity and functional group tolerance by using an iridium catalyst system. Notably

  黄酮是具有多种生物活性的重要天然产物。在这项研究中，通过使用简单的苯酚和内部炔烃作为底物，开发了一种黄酮羰基合成的新方法。通过使用铱催化剂体系，以中度到良好的收率分离出各种黄酮，具有出色的区域选择性和官能团耐受性。值得注意的是，这是直接将未预活化的苯酚和炔烃进行羰基环化以生成黄酮的例子，而配体的选择对这种转化的成功至关重要。
• Palladium-Catalyzed Carbonylative Synthesis of 2,3-Disubstituted Chromones
  作者：Chaoren Shen、Wanfang Li、Hongfei Yin、Anke Spannenberg、Troels Skrydstrup、Xiao-Feng Wu

  DOI：10.1002/adsc.201500858

  日期：2016.2.4

  An unexpected palladium‐catalyzed carbonylative synthesis of 2,3‐disubstituted chromones has been developed. Starting from 2‐bromofluorobenzenes and ketones, the corresponding chromones were produced in good yields. By control experiments, this transformation was found to proceed through a sequential carbonylation/Claisen–Hasse rearrangement/intramolecular nucleophilic aromatic substitution approach

  已经开发出了出乎意料的钯催化的2,3-二取代色酮的羰基合成。从2-溴氟苯和酮开始，以高收率生产了相应的色酮。由对照实验中，这种转变被发现通过连续的羰基化/克莱森-哈斯重排/分子内的亲核芳香取代的方法（S进行Ñ AR）。更具体地说，反应顺序始于酮与邻溴氟苯的钯催化羰基化反应，得到乙烯基苯甲酸酯，随后通过克莱森-哈斯重排将其转化为1,3-二酮。最终产物的分子内年代后产生Ñ的氩反应原位形成1,3-二酮。
• Nickel-catalyzed C–O/O–H Annulation of Salicylate Esters with Alkynes: Activation of C–O Bond in Esters
  作者：Yasuaki Iyori、Naoto Chatani

  DOI：10.1246/cl.200885

  日期：2021.3.5

  The Ni-catalyzed C−O/O−H annulation of salicylate esters with alkynes, leading to the production of chromone derivatives is reported. The key step in the reaction is the cleavage of an acyl C-O bond. The presence of a base is essential for the reaction to proceed.

  据报道，Ni催化水杨酸酯与炔烃的C-O / O-H环化反应，导致色酮衍生物的产生。反应中的关键步骤是裂解酰基CO键。碱的存在对于反应进行是必不可少的。
• Process for production of vinyl chloride polymer
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP0172427A2

  公开（公告）日：1986-02-26

  This process is a process for production of a vinyl chloride polymer by suspension polymerization or emulsion polymerization of vinyl chloride monomer or a mixture of vinyl chloride monomer with a vinyl monomer copolymerizable with said vinyl chloride monomer in an aqueous medium, characterized in that the polymerization is carried out in a polymerizer, the inner wall surface and portions of the auxiliary equipment thereof which may come into contact with the monomer during polymerization being previously coated with a scaling preventive comprising at least one selected from dyes, pigments and aromatic or heterocyclic compounds having at least 5 conjugated π bonds, while controlling the chloride ion concentration in the reaction mixture to not higher than 100 ppm. According to said process, scaling onto the inner wall surface of a polymerizer, etc. during polymerization can be prevented effectively and surely.

  该工艺是通过氯乙烯单体或氯乙烯单体与可与所述氯乙烯单体共聚的乙烯基单体混合物在水介质中进行悬浮聚合或乳液聚合来生产氯乙烯聚合物的工艺，其特征在于聚合是在聚合器中进行的、内壁表面及其辅助设备中可能在聚合过程中与单体接触的部分事先涂上一层防垢剂，该防垢剂至少包括一种选自染料、颜料和至少有 5 个共轭 π 键的芳香族或杂环化合物的防垢剂，同时控制反应混合物中的氯离子浓度不高于 100 ppm。根据上述工艺，可有效、可靠地防止聚合过程中聚合器等内壁表面结垢。
• Polymerization process characterized by a two layer coating against scale formation deposited using a steam carrier
  申请人：SHIN-ETSU CHEMICAL CO., LTD.

  公开号：EP0934955A1

  公开（公告）日：1999-08-11

  An improved process for producing a polymer by polymerizing a monomer having an ethylenic double bond in a polymerization vessel having a polymer scale preventive coating film on its inner wall surfaces, etc. is provided. The coating film is formed by coating a first coating liquid containing a compound selected from the group consisting of an aromatic compound having 5 or more conjugated π bonds and a heterocyclic compound having 5 or more conjugated π bonds, and then coating a second coating liquid on the first layer. The first and second coating liquids are applied by means of steam as a carrier. The second layer has a surface having a contact angle to water of less than 60° after its surface has been brought into contact with a solution of mixture of water and a vinyl chloride monomer in a weight ratio of 1:1, at 50°C for 1 hour. This process can shorten the time for forming the coating film to improve productivity, can improve the effect of preventing adhesion of polymer scale, can make colored particles less mix into polymer products obtained by this process, can lessen fish eyes and initial discoloring of formed products and can improve the quality of polymeric products and their formed or molded products.

  本发明提供了一种通过在聚合容器中聚合具有乙烯双键的单体来生产聚合物的改进工艺，该聚合容器的内壁表面等处具有聚合物防垢涂膜。该涂膜是通过涂覆第一涂覆液形成的，第一涂覆液含有选自具有 5 个或更多共轭 π 键的芳香族化合物和具有 5 个或更多共轭 π 键的杂环化合物的一组化合物，然后在第一层上涂覆第二涂覆液。第一种和第二种涂覆液通过蒸汽作为载体进行涂覆。第二层表面与水和氯乙烯单体重量比为 1:1 的混合物溶液在 50°C 下接触 1 小时后，其表面与水的接触角小于 60°。这种工艺可以缩短涂膜的形成时间，从而提高生产率；可以提高防止聚合物鳞片附着的效果；可以使有色颗粒较少地混入通过这种工艺获得的聚合物产品中；可以减少成型产品的鱼眼和初期褪色现象；可以提高聚合物产品及其成型或模塑产品的质量。