6-(benzyldimethylsilyl)-4-neopentyl-2-phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 6-(benzyldimethylsilyl)-4-neopentyl-2-phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione
• 英文别名: (3aS,4R,7aR)-6-[benzyl(dimethyl)silyl]-4-(2,2-dimethylpropyl)-2-phenyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione
• 化学式: C₂₈H₃₅NO₂Si
• 分子量: 445.677
• InChiKey: HCYONMZIKXXWOD-SDUSCBPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苯基马来酰亚胺 、 4,4-二甲基-1-戊烯 、 benzyldimethylsilylacetylene 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以51%的产率得到6-(benzyldimethylsilyl)-4-neopentyl-2-phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Ruthenium carbenes as catalysts in stereoselective ene–yne metathesis/Diels–Alder and ene–yne metathesis/Diels–Alder/cross coupling multicomponent reactions

  摘要：

  An ene-yne cross metathesis of silyl substituted alkynes and alkenes followed by a Diels-Alder reaction of the metathesis product 2-silyl-1,3-dienes has been developed. The dienes thus prepared in situ were shown to participate in highly diastereoselective Diels-Alder reactions. In one case the silicon substituted Diels-Alder cycloadduct was subsequently used without isolation and purification in a Hiyama cross coupling reaction. The cross coupling reactions enable these silicon dienes to be used as synthons for a variety of other dienes. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.011