diethyl 2-bromo-2-methyl malonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 2-bromo-2-methyl malonate
• 英文别名: DBMM；bromo-methyl-malonic acid ethyl ester methyl ester；1-O-ethyl 3-O-methyl 2-bromo-2-methylpropanedioate
• 化学式: C₇H₁₁BrO₄
• 分子量: 239.066
• InChiKey: OSVWIWZNOIXBLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  羟基脲 、 diethyl 2-bromo-2-methyl malonate 在 sodium methylate 作用下， 生成 6-methyl-3,5-dioxo-[1,2,4]oxadiazinane-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  Bennouna,C. et al., Journal of Heterocyclic Chemistry, 1979, vol. 16, p. 161 - 167

  摘要：

  DOI：

文献信息

• Copper-Catalyzed Intermolecular Aminoalkylation of Alkenes with α-Bromoalkyl Esters and Amines toward Pyrrolidin-2-ones
  作者：Gao-Hui Pan、Xuan-Hui Ouyang、Ming Hu、Ye-Xiang Xie、Jin-Heng Li

  DOI：10.1002/adsc.201700365

  日期：2017.8.7

  We here describe a new copper‐catalyzed tandem annulation of alkenes with α‐bromoalkyl esters and primary amines for producing polysubstituted pyrrolidin‐2‐ones. The reaction allows the formation of three new chemical bonds, one C–C bond and two C–N bonds, in a single reaction, and represents the first three‐component difunctionalization of alkenes for the synthesis of pyrrolidin‐2‐ones involving [2+2+1]

  我们在这里描述了一种新的铜催化的烯烃与α-溴代烷基酯和伯胺的串联聚合，用于生产多取代的吡咯烷酮-2-酮。该反应允许在一个反应​​中形成三个新的化学键，一个C–C键和两个C–N键，代表了用于合成吡咯烷酮-2-酮的烯烃的第一个三组分双官能化，涉及[2 + 2 + 1]。
• Copper-Catalyzed Three-Component Cascade Michael Addition/Heck-Type Alkylation/Annulation: Accessing Fully Substituted 1,3-Dihydro-2<i>H</i>-pyrrol-2-ones
  作者：Dan Ba、Yanhui Chen、Weiwei Lv、Si Wen、Guolin Cheng

  DOI：10.1021/acs.orglett.9b03189

  日期：2019.11.1

  We report a highly efficient copper-catalyzed three-component reaction of alkylamines, acetylenedicarboxylates, and alpha-bromocarbonyls for the assembly of fully substituted 1,3-dihydro-2H-pyrrol-2-ones. A variety of alkylamines and ammonium salt are functionalized with acetylenedicarboxylates and alpha-bromocarbonyls. N-aryl enam-inoesters are also successfully alkylated with alpha-bromocarbonyls. This protocol is understood to proceed through radical Heck-type coupling of in-situ-generated bulky trisubstituted alkenes with bulky tertiary alkyl bromides, which is realized for the first time.