4-(4-methoxyphenyl)-5,6-dihydro-2H-pyran-2-one | 1214319-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)-5,6-dihydro-2H-pyran-2-one
• 英文别名: 4-(4-Methoxyphenyl)-2,3-dihydropyran-6-one；4-(4-methoxyphenyl)-2,3-dihydropyran-6-one
• CAS: 1214319-57-9
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: BKRXPYOCVWWTHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苯硼酸 、 methyl 5-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2-pentynoate 在 copper (I) acetate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以86%的产率得到4-(4-methoxyphenyl)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis of 4-Aryl-Substituted Butenolides and Pentenolides by Copper-Catalyzed Hydroarylation

  摘要：

  We have investigated the effect of the type of protecting group used and the tether length of 4- and 5-hydroxy-substituted 2-alkynoates on the yields and selectivity of the product of hydroarylation. The use of methyl, methoxymethyl, and tert-butyldimethylsilyl (TBS) as protecting groups increased the total yield of the products. While the protected 4-hydroxy-2-butynoates afforded products formed from two or more alkyne substrates, 5-hydroxy-2-pentynoate derivatives exclusively yielded 1:1 adducts. These facts suggest that the product selectivity depends on the distance of the alkoxy group from the alkyne moiety rather than the type of the protecting group. Among the protecting groups used in this study, the TBS group was found to produce butenolides and pentenolides in good total yields via the one-pot hydroarylation/lactonization.

  DOI：

  10.3987/com-09-s(s)8

文献信息

• Ligand- and Base-Free Pd(II)-Catalyzed Controlled Switching between Oxidative Heck and Conjugate Addition Reactions
  作者：Sarah E. Walker、Julian Boehnke、Pauline E. Glen、Steven Levey、Lisa Patrick、James A. Jordan-Hore、Ai-Lan Lee

  DOI：10.1021/ol400539h

  日期：2013.4.19

  solvent allows controlled and efficient switching between oxidative Heck and conjugate addition reactions on cyclic Michael acceptor substrates, catalyzed by a cationic Pd(II) catalyst system. Both reactions are ligand- and base-free and tolerant of air and moisture, and the controlled switching sheds light on some of the factors which favor one reaction over the other.

  简单地改变溶剂即可在阳离子Pd（II）催化剂体系的催化下，在环迈克尔受体底物上的氧化Heck反应和共轭加成反应之间进行受控且有效的转换。两种反应均不含配体和碱，并且耐空气和湿气，并且受控的转换揭示了一些有利于一种反应优于另一种的因素。
• Selective arylation at the vinylic site of cyclic olefins
  作者：Xiaojin Wu、Jianrong (Steve) Zhou

  DOI：10.1039/c3cc41722k

  日期：——

  Cyclic olefins usually give Heck products having an aryl ring residing at the allylic or homoallylic position. We describe herein a new method that allows arylation at the vinylic position of various cyclic olefins.

  环烯烃通常得到具有在烯丙基或均烯丙基位置上的芳基环的Heck产物。我们在本文中描述了一种新的方法，该方法允许在各种环状烯烃的乙烯基位置进行芳基化。
• Palladium-Catalyzed Regioselective [5 + 1] Annulation of Vinyl Aziridines/Epoxides with ClCF₂COONa
  作者：Dandan Zuo、Tao Zhang、Jingjing Zhao、Wen Luo、Chaojie Wang、Pan Li

  DOI：10.1021/acs.orglett.2c01739

  日期：2022.7.1

  regioselective [5 + 1] annulation reactions of vinyl aziridines/epoxides with ClCF2COONa have been developed. Significantly, vinyl aziridines/epoxides act as heteroatom-containing five-atom synthons, and commercially available and cheap ClCF2COONa acts as the source of carbonyl serving as a difluorocarbene precursor. This protocol provides an efficient and practical method for the synthesis of δ-lactams and

  已经开发了钯催化的乙烯基氮丙啶/环氧化物与 ClCF 2 COONa 的区域选择性 [5 + 1] 环化反应。重要的是，乙烯基氮丙啶/环氧化物充当含杂原子的五原子合成子，而市售且廉价的 ClCF 2 COONa 充当用作二氟卡宾前体的羰基来源。该协议为以良好收率合成 δ-内酰胺和 δ-内酯提供了一种有效且实用的方法。
• 一种钯催化条件下合成α,β-不饱和杂环己基酮类化合物的方法
  申请人：河南大学

  公开号：CN114853664B

  公开（公告）日：2023-09-29

  本发明属于化合物制备技术领域，具体涉及一种钯催化条件下合成α,β‑不饱和杂环己基酮类化合物的方法，该方法是以式I所示的化合物和式II所示的ClCF2CO2Na为原料，在催化剂、配体、碱和溶剂作用下，所述催化剂为钯催化剂，在惰性气氛条件下发生环化反应，即烯基氮杂环丙烷/烯基环氧乙烷氧化开环，与ClCF2CO2Na提供的二氟卡宾形成配合物，该配合物在迁移插入和还原消除后，最终形成目标产物α,β‑不饱和杂环己基酮类化合物。本发明工艺简单，收率高。本发明中催化剂醋酸钯和配体三环己基膦，价格低，不需要过多处理；反应步骤简单，能以可观的产率获得相应产物。
• Rh–IndOlefOx catalyzed conjugate addition/Heck-type coupling of organoboronics to a lactam or a lactone
  作者：Noora Kuuloja、Matti Vaismaa、Robert Franzén

  DOI：10.1016/j.tet.2012.01.040

  日期：2012.3

  Four indole-olefin-oxazoline (IndOlefOx) ligands were synthesized and evaluated in Rh-catalyzed reactions between organoboronics and a lactam or a lactone. In addition to the expected conjugate addition products, the formation of significant amounts of Heck-type products was observed. The scope and limitations of these reactions were investigated. (C) 2012 Elsevier Ltd. All rights reserved.