(1S,2S,3S,4S)-6-Bromo-5-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-1-trimethylsilanyloxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester

• 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: (1S,2S,3S,4S)-6-Bromo-5-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-1-trimethylsilanyloxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (1S,2S,3S,4S)-6-bromo-5-[(2S)-2-(2-methoxypropan-2-yl)pyrrolidin-1-yl]-1-trimethylsilyloxy-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
• 化学式: C₂₁H₃₄BrNO₇Si
• 分子量: 520.493
• InChiKey: GUBXDVOOCFUVQM-OYZLTILVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (S)-1-(4-Bromo-2-methyl-5-trimethylsilanyloxy-furan-3-yl)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidine 、 富马酸二甲酯 生成 (1S,2S,3S,4S)-6-Bromo-5-[(S)-2-(1-methoxy-1-methyl-ethyl)-pyrrolidin-1-yl]-1-trimethylsilanyloxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Diastereoselective Diels-Alder Reactions Using Furan Substituted with a Nonracemic Amine

  摘要：

  The furan derivative 1 undergoes diastereoselective Diels-Alder reactions with dienophilic species such as alpha,beta-unsaturated esters, nitriles, sulfones, and imides in good to excellent chemical yields. The oxobicyclic adducts obtained are amenable to chemical transformations which render them useful to natural product synthesis.

  DOI：

  10.1021/jo00091a002