ethyl (1S,2S)-1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylenecyclohexane-1-carboxylate | 1256293-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (1S,2S)-1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylenecyclohexane-1-carboxylate
• CAS: 1256293-23-8
• 化学式: C₂₅H₄₆O₅Si
• 分子量: 454.723
• InChiKey: JSORBYAFCXIKKY-CZSZKKDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  ethyl 1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-cyclohexan-4-one-1-carboxylate 、 亚甲基三苯基膦烷 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.33h， 生成 ethyl (1S,2S)-1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylenecyclohexane-1-carboxylate 、 ethyl (1S,2R)-1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylenecyclohexane-1-carboxylate 、 ethyl (1R,2R)-1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylenecyclohexane-1-carboxylate
  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