dimethyl 2-(4-bromobut-2-yn-1-yl)-2-(but-2-yn-1-yl)malonate | 844821-48-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl 2-(4-bromobut-2-yn-1-yl)-2-(but-2-yn-1-yl)malonate
• 英文别名: dimethyl 2-(4-bromobut-2-ynyl)-2-(but-2-ynyl)malonate
• CAS: 844821-48-3
• 化学式: C₁₃H₁₅BrO₄
• 分子量: 315.164
• InChiKey: UNJQFFXNVXKABR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(4-bromobut-2-yn-1-yl)-2-(but-2-yn-1-yl)malonate 在 [Rh(OH)(cod)]2 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 (Z)-1,1-dimethoxylcarbonyl-3-[3,3-dimethoxylcarbonyl-5-((Z)-1-phenylethylidene)cyclopentylidene]-4-vinylcyclopentane
  参考文献：
  名称：

  Rhodium-Catalyzed Cyclization of 1,6-Enynes Triggered by Addition of Arylboronic Acids

  摘要：

  1,6-Enynes reacted with arylboronic acids in the presence of a catalytic amount of a rhodium(I) complex under mild conditions to give (Z)-1-(1-arylethylidene)-2-vinylcyclopentanes. The regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond triggered the cyclization process. Intramolecular carborhodation onto the pendent alkene in a 5-exo mode furnished a five-membered ring. Finally, the rhodium(I) methoxide generated by beta-methoxy elimination reacted with the arylboronic acid to promote the next catalytic cycle.

  DOI：

  10.1021/ja0435079
• 作为产物：
  描述：

  dimethyl propargylmalonate 、 1,4-二溴-2-丁炔 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以62%的产率得到dimethyl 2-(4-bromobut-2-yn-1-yl)-2-(but-2-yn-1-yl)malonate
  参考文献：
  名称：

  Rhodium-Catalyzed Cyclization of 1,6-Enynes Triggered by Addition of Arylboronic Acids

  摘要：

  1,6-Enynes reacted with arylboronic acids in the presence of a catalytic amount of a rhodium(I) complex under mild conditions to give (Z)-1-(1-arylethylidene)-2-vinylcyclopentanes. The regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond triggered the cyclization process. Intramolecular carborhodation onto the pendent alkene in a 5-exo mode furnished a five-membered ring. Finally, the rhodium(I) methoxide generated by beta-methoxy elimination reacted with the arylboronic acid to promote the next catalytic cycle.

  DOI：

  10.1021/ja0435079

文献信息

• Iron-Catalyzed Cycloaddition of Alkynenitriles and Alkynes
  作者：Brendan R. D’Souza、Timothy K. Lane、Janis Louie

  DOI：10.1021/ol2009939

  日期：2011.6.3

  The combination of Fe(OAc)(2) and an electron-donating, sterically hindered pyridyl bisimine ligand catalyzes the cycloaddition of alkynenitriles and alkynes. A variety of substituted pyridines were obtained in good yields.