2-(4-methoxyphenyl)-2,3-dihydro-4H-pyran-4-one | 60380-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenyl)-2,3-dihydro-4H-pyran-4-one
• 英文别名: 4H-Pyran-4-one, 2,3-dihydro-2-(4-methoxyphenyl)-；2-(4-methoxyphenyl)-2,3-dihydropyran-4-one
• CAS: 60380-11-2
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: RITOENHNMXHYGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  332.8±41.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-2,3-dihydro-4H-pyran-4-one 在 四丁基氟化铵 、 zinc trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 methyl 2-diazo-4-(6-(4-methoxyphenyl)-4-oxotetrahydro-2H-pyran-2-yl)-3-oxobutanoate
  参考文献：
  名称：

  Control of selectivity in the generation and reactions of oxonium ylides

  摘要：

  双铑催化的芳基取代四氢吡喃酮二氟乙酸酯的反应产生了意外的亚胺中间体，这些中间体生成了两种氧杂 bicyclo[4.2.1]-九氢庚烯的差向异构体，但通过增加芳基取代基的立体体积，可以形成单一的差向异构体。

  DOI：

  10.1039/c1cc12443a
• 作为产物：
  描述：

  (E)-1-Methoxy-5-(4-methoxy-phenyl)-5-trimethylsilanyloxy-pent-1-en-3-one 在 三氟乙酸 作用下， 生成 2-(4-methoxyphenyl)-2,3-dihydro-4H-pyran-4-one
  参考文献：
  名称：

  Nafion-H-catalyzed Mukaiyama aldol condensations and hetero Diels–Alder reactions using aldehydes and imines. Part 15: General synthetic methods

  摘要：

  Nafion-H catalyzes the Mukaiyama aldol condensation between aromatic aldehydes and the Danishefsky diene whereas the corresponding imines directly undergo hetero Diels-Alder cyclization to form 2,3-dihydro-gamma -pyridones. Some chiral acetal derived aldehydes were round to undergo Mukaiyama aldol condensation in the presence of Lewis acids but not with Nafion-H. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01592-1

文献信息

• A Lewis Base-catalyzed Hetero Diels–Alder Reaction between Aldehydes and the Danishefsky’s Diene
  作者：Teruaki Mukaiyama、Takayuki Kitazawa、Hidehiko Fujisawa

  DOI：10.1246/cl.2006.328

  日期：2006.3

  A lithium methoxide-catalyzed hetero Diels–Alder reaction of aromatic and aliphatic aldehydes with 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (Danishefsky’s diene) is described. It proceeds through the Mukaiyama-Aldol reaction pathway and affords the corresponding 2,3-dihydropyran-4-one skeletons in good to excellent yields.

  报道了由甲醇锂催化的芳香醛和脂肪醛与1-甲氧基-3-三甲基硅氧基-1,3-丁二烯（Danishefsky双烯）的杂Diels-Alder反应。该反应通过Mukaiyama-Aldol反应途径进行，并以优异的产率获得了相应的2,3-二氢吡喃-4-酮骨架。
• Hetero Diels−Alder Reactions of 1-Amino-3-siloxy-1,3-butadienes under Strictly Thermal Conditions
  作者：Yong Huang、Viresh H. Rawal

  DOI：10.1021/ol006404d

  日期：2000.10.1

  The hetero Diels-Alder reaction of 1-amino-3-siloxy-1,3-butadiene (1a) with a range of unactivated aldehydes proceeds readily under remarkably mild conditions: at room temperature and in the absence of Lewis acid catalysts. The cycloadducts are formed in good yields and can be converted directly to the corresponding dihydro-4-pyrones using acetyl chloride. Ketones and imines are also reactive in hetero

  1-氨基-3-甲硅烷氧基-1,3-丁二烯（1a）与一定范围的未活化醛的杂Diels-Alder反应在非常温和的条件下容易进行：在室温下和不存在路易斯酸催化剂的情况下。可以以高收率形成环加合物，并且可以使用乙酰氯将其直接转化为相应的二氢-4-吡喃酮。酮和亚胺在与该二烯的杂Diels-Alder反应中也具有反应性。
• CHIRAL DISULFONIMIDES
  申请人：List Benjamin

  公开号：US20110313150A1

  公开（公告）日：2011-12-22

  Chiral disulfonimides having the formula I to III, wherein at least one of the groups A and B in the compound of formula I, C and D of the compound in formula II, and E and F of the compound in formula III is a chiral group, or E and F together form a chiral backbone, X is C, Si, O, N or S, and n is 0, 1, 2, 3, 4, 5 or 6, where n is >1 only if X is C, and G is as defined herein, and to the organic salts, metal salts and metal complexes thereof, are suited as NMR shift reagents and as reagents for racemate splitting, and also as chiral Brønsted acid catalysts or chiral Lewis acid catalysts for activating ketones, aldehydes and alkenes, and also as catalysts in the organic synthesis.

  拥有I至III式的手性二磺酰胺，其中在式I化合物中的A和B基团中至少有一个是手性基团，在式II化合物中的C和D以及在式III化合物中的E和F中，E和F可以共同形成一个手性骨架，X为C、Si、O、N或S，n为0、1、2、3、4、5或6，当X为C时n>1，G如本文所定义，并且适用于其有机盐、金属盐和金属配合物，作为NMR位移试剂和对消旋体分离的试剂，还可作为手性Brønsted酸催化剂或手性Lewis酸催化剂，用于活化酮、醛和烯烃，以及作为有机合成中的催化剂。
• Facile Access to<i>cis</i>-2,6-Disubstituted Tetrahydropyrans by Palladium-Catalyzed Decarboxylative Allylation: Total Syntheses of (±)-Centrolobine and (+)-Decytospolides A and B
  作者：Jing Zeng、Yu Jia Tan、Jimei Ma、Min Li Leow、Davin Tirtorahardjo、Xue-Wei Liu

  DOI：10.1002/chem.201303328

  日期：2014.1.7

  facile synthesis of cis‐2,6‐disubstituted‐3,6‐dihydropyrans as cis‐2,6‐tetrahydropyran precursors has been achieved in high regio‐ and stereoselectivity with high yields. This reaction involves a palladium‐catalyzed decarboxylative allylation of various 3,4‐dihydro‐2H‐pyran substrates. Extending this reaction to 1,2‐unsaturated carbohydrates allowed the achievement of challenging β‐C‐glycosylation. Based

  顺式-2,6-四氢吡喃是生物活性天然产物的重要结构骨架。顺式-2,6-二取代-3,6-二氢吡喃前体作为顺式-2,6-四氢吡喃前体的简便合成方法具有很高的区域选择性和立体选择性，且收率很高。该反应涉及各种3,4-dihydro-2 H-吡喃底物的钯催化脱羧烯丙基化。将此反应扩展至1,2-不饱和碳水化合物可实现具有挑战性的β-C-糖基化。基于此方法，只需简单的步骤即可完成（±）-中心叶lob碱和（+）-去细胞肽A和B的总合成。
• Synthesis and Characterization of Pheox– and Phebox–Aluminum Complexes: Application as Tunable Lewis Acid Catalysts in Organic Reactions
  作者：Yoshihiro Nishimoto、Shuichi Nakao、Shota Machinaka、Fumiko Hidaka、Makoto Yasuda

  DOI：10.1002/chem.201901791

  日期：2019.8.14

  Pheox- and Phebox-aluminum complexes were synthesized and subsequently characterized by spectroscopic analysis. These complexes acted as Lewis acid catalysts, and their catalytic activities were controlled by using the Pheox, Phebox, and heteroatom ligands. The Pheox-aluminum complex exhibited an opposite substrate selectivity to AlCl3 in a competitive hetero-Diels-Alder reaction between electron-rich

  合成了Pheox-和Phebox-铝配合物，然后通过光谱分析对其进行了表征。这些络合物充当路易斯酸催化剂，并且通过使用Pheox，Phebox和杂原子配体控制其催化活性。在富电子醛和缺电子醛之间的竞争性杂狄尔斯-阿尔德反应中，Pheox-铝配合物对AlCl3具有相反的底物选择性。