methyl (E)-2-(3-oxobut-1-en-1-yl)benzoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-2-(3-oxobut-1-en-1-yl)benzoate
• 英文别名: Methyl 2-(3-oxobut-1-en-1-yl)benzoate；methyl 2-[(E)-3-oxobut-1-enyl]benzoate
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: PCMGQJKSNYWJJA-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-(3-oxobut-1-en-1-yl)benzoate 在 sodium hydride 、 palladium dichloride 作用下， 以 N,N-二甲基乙酰胺 、 mineral oil 为溶剂， 反应 0.25h， 以64%的产率得到2-乙酰基-1-茚酮
  参考文献：
  名称：

  氢化钠作为迈克尔供体在钯催化的α，β-不饱和羰基化合物还原反应中的应用

  摘要：

  在PdCl 2催化下，氢化钠被用作Michael供体，以减少α，β-不饱和羰基化合物的1,4-共轭还原，其具有操作简便，条件温和和高原子经济性的特点。NaH作为还原剂的优点通过合成复杂分子的一锅法或级联反应得到了证明。

  DOI：

  10.1002/adsc.201801676
• 作为产物：
  描述：

  3-(2-oxopropyl)-3H-isobenzofuran-1-one 在 乙醇 、 potassium carbonate 作用下， 生成 methyl (E)-2-(3-oxobut-1-en-1-yl)benzoate
  参考文献：
  名称：

  Fulda, Monatshefte fur Chemie, 1899, vol. 20, p. 713

  摘要：

  DOI：

文献信息

• A Selective and Benign Synthesis of Functionalized Benzalacetones <i>via</i> Mizoroki–Heck Reaction Using Aryldiazonium Salts
  作者：Therese Stern、Sven Rückbrod、Constantin Czekelius、Constanze Donner、Heiko Brunner

  DOI：10.1002/adsc.200900868

  日期：2010.10.9

  Palladium-catalyzed Mizoroki–Heck reactions were carried out in the presence of calcium carbonate in alcoholic solvents. Under these conditions an efficient preparation of functionalized benzalacetones was developed. The reactions were carried out at room temperature and aerobic conditions, giving the products within several minutes in up to 95% isolated yields. Furthermore, some kinetic investigations

  钯催化的Mizoroki-Heck反应是在碳酸钙存在下于醇类溶剂中进行的。在这些条件下，开发了一种高效制备功能化苯并丙酮的方法。反应在室温和有氧条件下进行，数分钟内获得产物，分离产率高达95％。此外，还介绍了一些动力学研究，机理见解和注意事项。
• Photocatalyzed Csp³–Csp³ cross-dehydrogenative coupling of <i>N</i>-Boc-tetrahydroisoquinolines with α,β-unsaturated ketones
  作者：Na-Ri-Mei Ao、Xue-Qing Zhu、Chun-Xin Zhao、Ya-Ru Gao、Yong-Qiang Wang

  DOI：10.1039/d1ob00527h

  日期：——

  A novel photocatalyzed cross-dehydrogenative coupling reaction of N-Boc-tetrahydroisoquinolines with α,β-unsaturated ketones has been developed. This research provides an easy access to a variety of C1-substituted tetrahydroisoquinolines, which can be further transformed into benzo[a]-quinolizine-2-ones, the skeletons of natural products with a wide range of biological activities. The load of the photocatalyst

  开发了一种新型光催化N -Boc-四氢异喹啉与 α,β-不饱和酮的交叉脱氢偶联反应。这项研究提供了一种容易获得各种 C1 取代的四氢异喹啉的方法，这些四氢异喹啉可以进一步转化为具有广泛生物活性的天然产物骨架苯并[ a ]-quinolizine-2-ones。光催化剂的负载量低，氧化剂便宜且毒性较小。
• APPLICATION OF METAL HYDRIDE/PALLADIUM COMPOUND SYSTEM IN PREPARATION OF 1,3-DICARBONYL COMPOUND IN CASCADE REACTION OF ELECTRON-DEFICIENT ALKENE COMPOUND
  申请人：SOOCHOW UNIVERSITY

  公开号：US20210206707A1

  公开（公告）日：2021-07-08

  Provided is an application of a metal hydride/palladium compound system in the preparation of a 1,3-dicarbonyl compound in a cascade reaction of an electron-deficient alkene compound, said reaction comprising the following steps: under the protection of nitrogen, a palladium compound and a metal hydride are suspended and stirred in a solvent, then an electron-deficient alkene compound is added; the mixture reacts at 0° C. to 100° C. for 0.3 to 10 hours; a saturated ammonium chloride aqueous solution is added to stop the reaction, and then extraction, drying by evaporation and purification by column chromatography are performed to obtain the product of 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used in the method are reagents easily obtained in a laboratory; compared with the commonly used methods of hydrogenation with hydrogen gas, the method can be easily operated, and has high safety, mild conditions and high reaction yield.

  提供了一种金属氢化物/钯化合物体系在电子亏化烯烃级联反应中制备1,3-二羰基化合物的应用。该反应包括以下步骤：在氮气保护下，将钯化合物和金属氢化物悬浮搅拌在溶剂中，然后加入电子亏化烯烃化合物；混合物在0°C至100°C反应0.3至10小时；加入饱和的氯化铵水溶液停止反应，然后进行萃取、蒸发干燥和柱层析纯化以获得1,3-二羰基化合物产物。该方法中使用的氢化物和钯化合物催化剂是实验室中易获得的试剂；与常用的氢气加氢方法相比，该方法操作简便，安全性高，条件温和，反应产率高。
• METHOD FOR PREPARING 1,3-DICARBONYL COMPOUND BASED ON METAL HYDRIDE/PALLADIUM COMPOUND SYSTEM
  申请人：SOOCHOW UNIVERSITY

  公开号：US20210206708A1

  公开（公告）日：2021-07-08

  Disclosed is a method for preparing a 1,3-dicarbonyl compound based on a metal hydride/palladium compound system. The method includes the following steps: suspending a palladium compound and a metal hydride in a solvent under the protection of nitrogen, then adding an electron-deficient olefin compound, reacting same at 0° C.-100° C. for 0.3 to 10 hours, then adding a saturated ammonium chloride aqueous solution to stop the reaction, and then subjecting same to extraction, evaporation until dryness, and column chromatography purification to obtain the 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used by the present invention are reagents easily obtained in a laboratory. Compared to a common hydrogen hydrogenation method, the method is easier to operate, and has a higher safety, mild conditions, and a high reaction yield.

  本方法揭示了一种基于金属氢化物/钯化合物体系制备1,3-二酮化合物的方法。该方法包括以下步骤：在氮气保护下将钯化合物和金属氢化物悬浮在溶剂中，然后添加一个电子亏缺的烯烃化合物，在0℃-100℃下反应0.3至10小时，然后加入饱和铵盐水溶液停止反应，然后进行提取、蒸发至干燥，并进行柱层析纯化以获得1,3-二酮化合物。本发明使用的氢化物和钯化合物催化剂是实验室中容易获得的试剂。与常见的氢气加氢方法相比，该方法操作更简单，安全性更高，条件温和，反应产率也更高。
• Method for preparing 1,3-dicarbonyl compound based on metal hydride/palladium compound system
  申请人：SOOCHOW UNIVERSITY

  公开号：US11180437B2

  公开（公告）日：2021-11-23

  Disclosed is a method for preparing a 1,3-dicarbonyl compound based on a metal hydride/palladium compound system. The method includes the following steps: suspending a palladium compound and a metal hydride in a solvent under the protection of nitrogen, then adding an electron-deficient olefin compound, reacting same at 0° C.-100° C. for 0.3 to 10 hours, then adding a saturated ammonium chloride aqueous solution to stop the reaction, and then subjecting same to extraction, evaporation until dryness, and column chromatography purification to obtain the 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used by the present invention are reagents easily obtained in a laboratory. Compared to a common hydrogen hydrogenation method, the method is easier to operate, and has a higher safety, mild conditions, and a high reaction yield.

  本发明公开了一种基于金属氢化物/钯化合物体系制备 1，3-二羰基化合物的方法。该方法包括以下步骤：在氮气保护下将钯化合物和金属氢化物悬浮在溶剂中，然后加入缺电子的烯烃化合物，在 0° C.-100° C 下反应 0.3 - 10 小时，然后加入饱和氯化铵水溶液以停止反应，然后进行萃取、蒸发至干和柱层析纯化以获得 1,3-二羰基化合物。本发明使用的氢化物和钯化合物催化剂都是在实验室中很容易获得的试剂。与普通氢氢化方法相比，该方法操作简便，安全性高，条件温和，反应产率高。