dimethyl 2,4-bis(4-bromobenzoyl)pentanedioate | 1186485-58-4

• 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-bromobenzoyl)pentanedioate
• CAS: 1186485-58-4
• 化学式: C₂₁H₁₈Br₂O₆
• 分子量: 526.178
• InChiKey: JHMUZHXJNQTROH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(4-溴苯基)-3-氧丙酸甲酯 在 gold(III) chloride 、 硝基甲烷 作用下， 反应 2.5h， 以88%的产率得到dimethyl 2,4-bis(4-bromobenzoyl)pentanedioate
  参考文献：
  名称：

  Gold/copper-catalyzed activation of the aci-form of nitromethane in the synthesis of methylene-bridged bis-1,3-dicarbonyl compounds

  摘要：

  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。

  DOI：

  10.1039/c1cc14926a

文献信息

• 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。
• Diamine-mediated degradative dimerisation of Morita–Baylis–Hillman ketones
  作者：Ajit Kumar Jha、Anju Kumari、Srinivasan Easwar

  DOI：10.1039/c9cc10068g

  日期：——

  A degradative dimerisation of Morita-Baylis-Hillman ketones was observed in the presence of a primary diamine. The reaction proceeded swiftly to produce methylene-bridged 1,3-dicarbonyl compounds. A brief mechanistic investigation alluded to a retro-Mannich reaction as the key step of the transformation.

  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。
• Metal-Free Csp3–N Bond Cleavage of Amides Using tert-Butyl Hydroperoxide as Oxidant
  作者：Hu Cai、Shengmei Guo、Zheng Zhu、Lin Lu、Wenbiao Zhang、Jiuhan Gong

  DOI：10.1055/s-0034-1379879

  日期：——

  A mild and efficient protocol for the metal-free C-N bond-cleavage of amides has been developed. The methodology employs iodine as a catalyst to cleave the C(Me)-N bond of dimethylformamide or dimethylacetamide, providing novel access to methylene-bridged bis-1,3-dicarbonyl compounds instead of enol carbamates in the presence of tert-butyl hydroperoxide.