5,6-benzo-4-(4-methoxyphenyl)-3,4-dihydrobenzopyran-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 5,6-benzo-4-(4-methoxyphenyl)-3,4-dihydrobenzopyran-2-one
• 英文别名: 1-(4-Methoxyphenyl)-1,2-dihydrobenzo[f]chromen-3-one；1-(4-methoxyphenyl)-1,2-dihydrobenzo[f]chromen-3-one
• 化学式: C₂₀H₁₆O₃
• 分子量: 304.345
• InChiKey: BIINAUYWWHAJFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 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-甲氧基肉桂酸 、 2-萘酚 在 碘 作用下， 以 neat (no solvent) 为溶剂， 反应 4.0h， 以85%的产率得到5,6-benzo-4-(4-methoxyphenyl)-3,4-dihydrobenzopyran-2-one
  参考文献：
  名称：

  Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling

  摘要：

  Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I-2 while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I-2. Later reaction occurs via a tandem hydroarylation-esterification process at 120-130 degrees C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in 5-85% yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.093

文献信息

• Transition-Metal-Free Arylation and Alkylation of Diarylmethyl <i>p</i>-Tolyl Sulfones with Zinc Reagents
  作者：Maozhong Miao、Wenguang Yin、Lei Wang、Zhengkai Chen、Jianfeng Xu、Hongjun Ren

  DOI：10.1021/acs.joc.8b01428

  日期：2018.9.7

  The transition-metal-free synthesis of unsymmetrical and highly functionalized triarylmethanes through arylation of the situ generated o-QMs from diarylmethyl p-tolyl sulfones with aryl zinc reagents is described. Alkyl zinc reagents are also well tolerated in this reaction. Additionally, the straightforward synthesis of the analogue of the antituberculosis agent A and the key precursor of the anti-breast-cancer

  描述了不对称金属和高度官能化的三芳基甲烷的无过渡金属合成，该芳基通过芳基锌试剂芳基化二芳基甲基对甲苯砜中的原位生成的o- QM来合成。烷基锌试剂在该反应中也具有良好的耐受性。另外，通过该策略实现了抗结核剂A的类似物和抗乳腺癌剂B的关键前体的直接合成。
• An Efficient and One-Pot Synthesis of 1,2-Dihydro-3H-Naphtho[2,1-b]Pyran-3-Ones
  作者：Azam Abdolrazaghnezhad、Alireza Hassanabadi

  DOI：10.3184/174751915x14360187398046

  日期：2015.7

  Three-component and one-pot, reaction between β-naphthol, Meldrum's acid and aryl aldehydes in the presence of piperidine affords 1-aryl-1,2-dihydro-3H-naphtho[2,1-b]pyran-3-ones in excellent yields.

  在哌啶存在下，β-萘酚、梅尔德鲁姆酸和芳基醛发生三组分反应，并在一锅中生成 1-芳基-1,2-二氢-3H-萘并[2,1-b]吡喃-3-酮，收率极高。
• A Simple and Green Approach for the Synthesis of Tetrahydrobenzo[a]-xanthen-11-one Derivatives Using Tetrabutyl Ammonium Fluoride in Water
  作者：Ching-Fa Yao、Shijay Gao、Chen Tsai

  DOI：10.1055/s-0028-1088214

  日期：2009.4

  An efficient and simple procedure for the synthesis of 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives has been described. This one-pot multicomponent reaction involves the reaction of aldehydes, 2-naphthol, and cyclic 1,3-diketones in the presence of catalytic amount of recyclable TBAF in water.

  已描述一种高效简单的合成12-芳基或12-烷基-8,9,10,12-四氢苯并[a]荧蒽-11-酮衍生物的程序。这种“一锅法”多组分反应涉及在可回收的催化剂TBAF（四丁基氟化铵）存在下，用水作为溶剂，反应醛、2-萘酚和环状1,3-二酮。
• A novel method for the synthesis of tetrahydrobenzo[a]-xanthen-11-one derivatives using cerium(III) chloride as a highly efficient catalyst
  作者：Mazaahir Kidwai、Anwar Jahan、Neeraj Kumar Mishra

  DOI：10.1016/j.crci.2012.01.002

  日期：2012.4

  Résumé Cerium(III) chloride is found to be an highly efficient catalyst for the addition of aldehydes, β-naphthol and cyclic 1,3-dicarbonyl compounds/Meldrum's acid via a multicomponent reaction. The easy availability of starting materials, novel and eco-friendly procedure makes this strategy more useful for the preparation of tetrahydrobenzo[a]-xanthen-11-one, and benzo[f]chromen-3-one derivatives.

  摘要 氯化铈(III)被发现是一种高效的催化剂，可通过多组分反应促进醛、β-萘酚和环状1,3-二酮化合物/梅尔德朗酸的加成。起始材料易于获取，工艺新颖且环保，使得这种策略在制备四氢苯并[a]喹啉-11-酮和苯并[f]色烯-3-酮衍生物方面更加实用。
• A convenient synthesis of dihydrocoumarins from phenols and cinnamic acid derivatives
  作者：Shinya Aoki、Chie Amamoto、Juzo Oyamada、Tsugio Kitamura

  DOI：10.1016/j.tet.2005.07.062

  日期：2005.9

  A facile procedure for synthesis of dihydrocoumarin derivatives was described. Although the yield of the products in the reaction of phenols with acrylates in trifluoroacetic acid in the presence of Pd(OAc)2 giving coumarins was found to be very low, dihydrocoumarin derivatives were obtained in good to high yields in the absence of Pd(OAc)2 when ethyl cinnamates bearing electron-donating groups were

  描述了合成二氢香豆素衍生物的简便方法。尽管发现在Pd（OAc）2存在下，苯酚与丙烯酸酯在三氟乙酸中反应生成香豆素的产物的收率很低，但在没有Pd（OAc）的情况下，二氢香豆素衍生物的收率高到高。 ）2当在该反应中使用带有给电子基团的肉桂酸乙酯时。