methyl (3S,4R,5R)-3-[tert-butyl(diphenyl)silyl]oxy-4,5-dihydroxycyclohexene-1-carboxylate | 244231-01-4

• 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: methyl (3S,4R,5R)-3-[tert-butyl(diphenyl)silyl]oxy-4,5-dihydroxycyclohexene-1-carboxylate
• CAS: 244231-01-4
• 化学式: C₂₄H₃₀O₅Si
• 分子量: 426.585
• InChiKey: BBXKFBRQTAKOMG-BHIFYINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (3S,4R,5R)-3-[tert-butyl(diphenyl)silyl]oxy-4,5-dihydroxycyclohexene-1-carboxylate 在 四氧化锇 、 camphor-10-sulfonic acid 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  A Class of C₂ and Pseudo C₂ Symmetric Ketone Catalysts for Asymmetric Epoxidation. Conformational Effect on Catalysis

  摘要：

  A class of C-2 and pseudo C-2 symmetric ketones with one fused ring at each side of the carbonyl group have been prepared from quinic acid and found to be effective catalysts for the asymmetric epoxidation of a variety of olefins. Electron deficient olefins such as enones can be efficiently epoxidized. Encouragingly good enantioselectivity is also obtained for the epoxidation of styrenes. The studies show that the ketone conformation plays an important role in the reactivity and selectivity of the catalyst.

  DOI：

  10.1021/jo9908849
• 作为产物：
  描述：

  methyl (3aR,7S,7aS)-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate 在 咪唑 、 4-二甲氨基吡啶 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 methyl (3S,4R,5R)-3-[tert-butyl(diphenyl)silyl]oxy-4,5-dihydroxycyclohexene-1-carboxylate
  参考文献：
  名称：

  A Class of C₂ and Pseudo C₂ Symmetric Ketone Catalysts for Asymmetric Epoxidation. Conformational Effect on Catalysis

  摘要：

  A class of C-2 and pseudo C-2 symmetric ketones with one fused ring at each side of the carbonyl group have been prepared from quinic acid and found to be effective catalysts for the asymmetric epoxidation of a variety of olefins. Electron deficient olefins such as enones can be efficiently epoxidized. Encouragingly good enantioselectivity is also obtained for the epoxidation of styrenes. The studies show that the ketone conformation plays an important role in the reactivity and selectivity of the catalyst.

  DOI：

  10.1021/jo9908849

文献信息

• The stereocontrolled formation of cyclic vicinal cis-diols via a samarium diiodide pinacol coupling of dialdehydes
  作者：Jose Luis Chiara、Walter Cabri、Stephen Hanessian

  DOI：10.1016/s0040-4039(00)92024-0

  日期：1991.2

  Aliphatic 1,5- and 1,6 dialdehydes with and without α-substituents, as well as derivatives of carbohydrate dialdehydes undergo a pinacol coupling reaction in the presence of SmI2 to give cis-diols as the preponderant products. When α-alkoxy groups are present, the diol has an orientation that is opposite to such groups.

  具有和不具有α-取代基的脂肪族1,5-和1,6二醛以及碳水化合物二醛的衍生物在SmI 2的存在下进行频哪醇偶联反应，以顺式二醇为主的产物。当存在α-烷氧基时，二醇具有与这样的基团相反的取向。