dimethyl 2,4-bis(4-methoxybenzoyl)pentanedioate | 1186485-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 2,4-bis(4-methoxybenzoyl)pentanedioate
• CAS: 1186485-57-3
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: PTMAJNVZWXAPPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 2-(4-methoxybenzoyl)acrylate 在 乙二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以74%的产率得到dimethyl 2,4-bis(4-methoxybenzoyl)pentanedioate
  参考文献：
  名称：

  二胺介导的森田-贝利斯-希尔曼酮的降解性二聚。

  摘要：

  在伯二胺存在下，观察到森田-贝利斯-希尔曼酮的降解性二聚化。反应迅速进行以产生亚甲基桥连的1，3-二羰基化合物。简短的机械研究暗示了曼尼奇的后反应是这一转变的关键步骤。

  DOI：

  10.1039/c9cc10068g

文献信息

• Gold/copper-catalyzed activation of the aci-form of nitromethane in the synthesis of methylene-bridged bis-1,3-dicarbonyl compounds
  作者：Rengarajan Balamurugan、Seetharaman Manojveer

  DOI：10.1039/c1cc14926a

  日期：——

  Activation of the aci-form of nitromethane using Lewis acids for the attack of carbon nucleophiles was studied. 1,3-Dicarbonyl compounds in the presence of catalytic amounts of AuCl3 or Cu(OTf)2 in nitromethane solvent could be converted into methylene-bridged bis-1,3-dicarbonyl compounds.

  使用Lewis酸激活硝基甲烷的酸形式，以进行碳亲核试剂的攻击的研究已经开展。在催化量的AuCl₃或Cu(OTf)₂存在的条件下，硝基甲烷溶剂中的1,3-二羰基化合物可以转化为亚甲基桥联的双1,3-二羰基化合物。
• Aerobic Oxidation of a Tertiary Aliphatic Amine Under Visible-Light Photocatalysis: Facile Synthesis of Methylene-Bridged Bis-1,3-dicarbonyl Compounds
  作者：Woo-Jin Yoo、Arata Tanoue、Shū Kobayashi

  DOI：10.1002/asia.201200807

  日期：2012.12

  Lights, camera, action! An efficient protocol for the formation of methylene‐bridged bis‐1,3‐dicarbonyl compounds has been developed through an aerobic photocatalytic oxidative coupling reaction between 1,3‐dicarbonyl compounds and a tertiary aliphatic amine.

  灯光，摄像头，动作！通过1,3-二羰基化合物与脂族叔胺之间的需氧光催化氧化偶联反应，已开发出形成亚甲基双bis-1,3-二羰基化合物的有效方法。
• Iron-Catalyzed Selective Oxidation of <i>N</i>-Methyl Amines: Highly Efficient Synthesis of Methylene-Bridged bis-1,3-Dicarbonyl Compounds
  作者：Haijun Li、Zhiheng He、Xingwei Guo、Wenjuan Li、Xuhui Zhao、Zhiping Li

  DOI：10.1021/ol901751c

  日期：2009.9.17

  Methylene-bridged bis-1,3-dicarbonyl derivatives were synthesized efficiently by iron-catalyzed oxidative reactions of 1,3-dicarbonyl compounds and N,N-dimethylaniline. Bipyrazoles and substituted 1,4-dihydropyridine were obtained by the reactions of bis-1,3-dicarbonyl compounds with hydrazines and ammonium acetate, respectively.

  亚铁桥联的双1,3-二羰基衍生物是通过铁催化的1,3-二羰基化合物与N，N-二甲基苯胺的氧化反应而有效合成的。联吡唑和取代的1,4-二氢吡啶分别通过双-1,3-二羰基化合物与肼和乙酸铵的反应制得。
• Benzannulation and <i>N</i> ‐Annulation of β‐Ketoenamines for Synthesizing Aniline and Pyridine Derivatives Using DMSO as a Methine Source
  作者：Pallaba Ganjan Dalai、Niranjan Panda

  DOI：10.1002/adsc.202200886

  日期：2022.11.8

  N-annulation of β-ketoenamines by the in-situ generated methyl(methylene)sulfonium ion from the reaction of dimethyl sulfoxide (DMSO) and 1,2-dibromoethane (DBE) was achieved. The β-ketoenamines underwent N-annulation to pyridine derivatives, while the N-alkylated enamines were benzannulated to afford substituted anilines. The utility of the intermediate methyl(methylene)sulfonium ion was further extended for

  通过二甲基亚砜（DMSO）和1,2-二溴乙烷（DBE）的反应原位产生的甲基（亚甲基）锍离子实现了β-酮烯胺的苯环化和N-环化。β-酮烯胺经 N-环化生成吡啶衍生物，而N-烷基化烯胺经苯环化生成取代的苯胺。中间体甲基（亚甲基）锍离子的用途进一步扩展用于合成亚甲基桥联双-1,3-二羰基化合物。
• Facile synthesis of bis-1,3-dicarbonyl compounds using inert dichloromethane as a one-carbon source
  作者：Li-Ming Jiang、Kai Xiang、Hai-Juan Jiao、Jing-Lin Yang、Heng-Tong Qu、Xue-Tao Xu、Wen-Bao、Dao-Yong Zhu、Shao-Hua Wang

  DOI：10.1016/j.tetlet.2023.154564

  日期：2023.6

  simple and convenient procedure for the preparation of valuable bis-1,3-dicarbonyl-substituted methane compounds and their derivatives has been developed using inert dichloromethane as one-carbon source in good to excellent yields. The advantages of this protocol are mild reaction conditions, easily scalable and good functional group compatibility. Moreover, the use of cyclic secondary amine as the promoter

  使用惰性二氯甲烷作为单碳源，开发了一种制备有价值的双-1,3-二羰基取代的甲烷化合物及其衍生物的简单方便的方法，收率良好。该协议的优点是反应条件温和、易于扩展和良好的功能组兼容性。此外，使用环状仲胺作为促进剂避免了过渡金属催化剂和氧化剂的存在。