ethyl (1S,2S)-1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-cyclohexen-4-one-1-carboxylate | 1256293-20-5

• 分子结构分类: 有机化合物
• 英文名称: ethyl (1S,2S)-1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-5-cyclohexen-4-one-1-carboxylate
• 英文别名: ethyl (1S,6S)-1-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-oxocyclohex-2-ene-1-carboxylate
• CAS: 1256293-20-5
• 化学式: C₂₄H₄₂O₆Si
• 分子量: 454.679
• InChiKey: UVBFJAYOMULSIT-NMMYMHLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 ethyl 2-(4''-(tert-butyldimethylsilyloxy)butyl)-3-((R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-acrylate 反应 47.0h， 以17%的产率得到ethyl (E)-2-(4''-(tert-butyldimethylsilyloxy)butyl)-3-((R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-acrylate
  参考文献：
  名称：

  Synthesis of a Functionalized 7,6-Bicyclic Spiroimine Ring Fragment of the Spirolides

  摘要：

  The asymmetric synthesis of a functionalized 7,6-spiroimine related to the spirolides is described. Intermolecular Diels-Alder cycloaddition of a chiral trisubstituted dienophile and Danishefsky's diene enabled simultaneous installation of the C7 and C29 stereocenters. Further transformations and late-stage aza-Wittig cyclization afforded the spiroimine in good yield. During this study, an unprecedented 14-membered dialdimine was also obtained.

  DOI：

  10.1021/ol102525w