2-(2-Methyl-1-trimethylsilanyloxy-propyl)-5-oxo-cyclopent-1-enecarboxylic acid ethyl ester | 128114-19-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-(2-Methyl-1-trimethylsilanyloxy-propyl)-5-oxo-cyclopent-1-enecarboxylic acid ethyl ester
• 英文别名: Ethyl 2-(2-methyl-1-trimethylsilyloxypropyl)-5-oxocyclopentene-1-carboxylate
• CAS: 128114-19-2
• 化学式: C₁₅H₂₆O₄Si
• 分子量: 298.455
• InChiKey: RHEJJHGILAFLCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-乙氧基-1-三甲硅氧基环丙烷 、 ethyl 4-hydroxy-5-methyl-2-hexynoate 在 copper(I) bromide dimethylsulfide complex zinc(II) chloride 作用下， 生成 2-(2-Methyl-1-trimethylsilanyloxy-propyl)-5-oxo-cyclopent-1-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  Addition of zinc homoenolates to acetylenic esters and amides: a formal [3 + 2] cycloaddition

  摘要：

  The copper-catalyzed conjugate addition-cycloacylation reaction of zinc homoenolates with acetylenic esters or acetylenic amides is described. The zinc homoenolate is prepared from [(ethoxycyclopropyl)oxy]trimethylsilane and zinc chloride in ether. Addition of an acetylenic amide or ester provides 2-carboxamido-or 2-carboalkoxy-3-alkylcyclopent-2-en-1-ones in good to excellent yields. The reaction can be carried out in the presence of a variety of sensitive functional groups including epoxides, alpha,beta-unsaturated esters, acetals, silyl ethers, and furans.

  DOI：

  10.1021/jo00057a013

文献信息

• Addition of zinc homoenolates to acetylenic esters: a formal [3+2] cycloaddition
  作者：Michael T. Crimmins、Philippe G. Nantermet

  DOI：10.1021/jo00301a003

  日期：1990.7
• CRIMMINS, MICHAEL T.;NANTERMET, PHILIPPE G., J. ORG. CHEM., 55,(1990) N4, C. 4235-4237
  作者：CRIMMINS, MICHAEL T.、NANTERMET, PHILIPPE G.

  DOI：——

  日期：——