(1S,2S,4'R)-(1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylenecyclohexyl)methanol | 1256293-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,4'R)-(1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylenecyclohexyl)methanol
• 英文别名: [(1S,2S)-1-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylidenecyclohexyl]methanol
• CAS: 1256293-24-9
• 化学式: C₂₃H₄₄O₄Si
• 分子量: 412.685
• InChiKey: QICNOPQWHIKERW-ZRCGQRJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,4'R)-(1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylenecyclohexyl)methanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以86%的产率得到(1S,2S,4'R)-1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylenecyclohexane-1-carbaldehyde
  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
• 作为产物：
  描述：

  ethyl 1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-((4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylenecyclohexane-1-carboxylate 在 lithium aluminium tetrahydride 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以62%的产率得到(1S,2S,4'R)-(1-(4''-(tert-butyldimethylsilyloxy)butyl)-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylenecyclohexyl)methanol
  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