(1R,2S,5R,6S)-3,4-Bis-trimethylsilanyloxy-tricyclo[4.2.2.0^2,5]deca-3,7-diene | 39762-44-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R,2S,5R,6S)-3,4-Bis-trimethylsilanyloxy-tricyclo[4.2.2.0^2,5]deca-3,7-diene
• 英文别名: trimethyl-[[(1R,2S,5R,6S)-4-trimethylsilyloxy-3-tricyclo[4.2.2.02,5]deca-3,7-dienyl]oxy]silane
• CAS: 39762-44-2
• 化学式: C₁₆H₂₈O₂Si₂
• 分子量: 308.568
• InChiKey: CDWOPKJTOVFCFN-KPWCQOOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R,6S)-3,4-Bis-trimethylsilanyloxy-tricyclo[4.2.2.0^2,5]deca-3,7-diene 在 lipase PS-on-Celite 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 19.0h， 生成 (-)-(1R,2S,3S,5R,6S)-3-hydroxytricyclo[4.2.2.0^2,5]dec-7-en-4-one
  参考文献：
  名称：

  Lipase-mediated kinetic resolution of tricyclic acyloins, endo-3-hydroxytricyclo[4.2.1.02,5]non-7-en-4-one and endo-3-hydroxytricyclo[4.2.2.02,5]dec-7-en-4-one

  摘要：

  Kinetic resolution of tricyclic acyloins, endo-3-hydroxytricyclo[4.2.1.0(2,5)]non-7-en-4-one and endo-3-hydroxytricyclo[4.2.2.0(2,5)]dec-7-en-4-one, and their acetates has been examined using a lipase. It has been found that a facile and stereoselective kinetic resolution occurs both in organic solvent and an aqueous solution in enantiocomplementary ways to afford both enantiomers of the acyloins and their acetates in enantiomerically pure forms. Enantiomerization of (+)-acyloins leading to (-)-acyloin acetates has also been achieved by the same lipase in an organic solvent by addition of a catalytic amount of triethylamine. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00336-4
• 作为产物：
  描述：

  dimethyl endo,endo-bicyclo<2.2.2>oct-5-ene-2,3-dicarboxylate 、 三甲基氯硅烷 生成 (1R,2S,5R,6S)-3,4-Bis-trimethylsilanyloxy-tricyclo[4.2.2.0^2,5]deca-3,7-diene
  参考文献：
  名称：

  ALBERT, B.;HELLER, C.;IDEN, R.;MARTIN, G.;MARTIN, H. -D.;MAYER, B.;OFTRIN+, ISRAEL J. CHEM., 1985, 25, N 1, 74-83

  摘要：

  DOI：

文献信息

• SYNTHESIS AND [2+2]-CYCLOREVERSION OF CAGE KETONES
  作者：Yoshiro Yamashita、Toshio Mukai

  DOI：10.1246/cl.1984.1741

  日期：1984.10.5

  A series of pentacyclic cage ketones 2b-d having no substituent was synthesized by the photochemical [2+2]-cycloaddition reaction of corresponding tricyclic dienones 1b-d. The cage ketones 2b-d underwent thermal [2+2]-cycloreversion to give dienones 1b-d. The reactivities were dependent on the length of the bridge “X”.

  通过相应的三环二烯酮1b-d的光化学[2+2]-环加成反应合成了一系列无取代基的五环笼酮2b-d。笼酮 2b-d 经历了热 [2+2]-环转化，得到二烯酮 1b-d。反应性取决于桥“X”的长度。