(1R,2S,6R)-2-[[[(2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,3-dimethylbutyl]-methylamino]methyl]-6-(hydroxymethyl)-4,4-dimethylcyclohexan-1-ol | 205943-65-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,6R)-2-[[[(2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,3-dimethylbutyl]-methylamino]methyl]-6-(hydroxymethyl)-4,4-dimethylcyclohexan-1-ol
• CAS: 205943-65-3
• 化学式: C₂₄H₅₁NO₃Si
• 分子量: 429.759
• InChiKey: IHBMWONZWRJVSB-DOIPELPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,6R)-2-[[[(2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,3-dimethylbutyl]-methylamino]methyl]-6-(hydroxymethyl)-4,4-dimethylcyclohexan-1-ol 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (1R,2S,6R)-2-[[[(2R)-2-(hydroxymethyl)-3,3-dimethylbutyl]-methylamino]methyl]-4,4-dimethyl-6-(3-phenylmethoxypropoxymethoxymethyl)cyclohexan-1-ol
  参考文献：
  名称：

  Stepwise Approach toward First Generation Nonenzymatic Hydrolases

  摘要：

  The synthesis and reactivity study of a first generation serine protease mimic is described. Central in the design stands the possibility of stabilization of the transition state by an amino triol such as 8t. En route to 8t, a series of amino alcohols (4-8) was obtained, the reactivity of which was studied toward esterification by acetylimidazole (AcIm) and by p-nitro-2,2,2-trifluoroacetanilide (PNTFA). Interesting reactivity differences were observed between the cis-and the trans-series, especially between 7c and 7t (AcIm), and between 8c and 8t (PNTFA). In both cases the results are explained by invoking extra stabilization of the tetrahedral oxyanion.

  DOI：

  10.1021/jo971935+
• 作为产物：
  描述：

  4,4-二甲基环己酮 在 咪唑 、 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 、 四丁基氟化铵 、 氨 、 三氧化硫吡啶 、 lithium 、 sodium hydride 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 51.83h， 生成 (1R,2S,6R)-2-[[[(2R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,3-dimethylbutyl]-methylamino]methyl]-6-(hydroxymethyl)-4,4-dimethylcyclohexan-1-ol
  参考文献：
  名称：

  Stepwise Approach toward First Generation Nonenzymatic Hydrolases

  摘要：

  The synthesis and reactivity study of a first generation serine protease mimic is described. Central in the design stands the possibility of stabilization of the transition state by an amino triol such as 8t. En route to 8t, a series of amino alcohols (4-8) was obtained, the reactivity of which was studied toward esterification by acetylimidazole (AcIm) and by p-nitro-2,2,2-trifluoroacetanilide (PNTFA). Interesting reactivity differences were observed between the cis-and the trans-series, especially between 7c and 7t (AcIm), and between 8c and 8t (PNTFA). In both cases the results are explained by invoking extra stabilization of the tetrahedral oxyanion.

  DOI：

  10.1021/jo971935+

文献信息

• Stepwise Approach toward First Generation Nonenzymatic Hydrolases
  作者：Annemieke Madder、Pierre J. De Clercq、Jean-Paul Declercq

  DOI：10.1021/jo971935+

  日期：1998.4.1

  The synthesis and reactivity study of a first generation serine protease mimic is described. Central in the design stands the possibility of stabilization of the transition state by an amino triol such as 8t. En route to 8t, a series of amino alcohols (4-8) was obtained, the reactivity of which was studied toward esterification by acetylimidazole (AcIm) and by p-nitro-2,2,2-trifluoroacetanilide (PNTFA). Interesting reactivity differences were observed between the cis-and the trans-series, especially between 7c and 7t (AcIm), and between 8c and 8t (PNTFA). In both cases the results are explained by invoking extra stabilization of the tetrahedral oxyanion.