tert-butyldimethylsilyloxy(1-methyl-2-pyrrolyl)acetonitrile | 223442-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tert-butyldimethylsilyloxy(1-methyl-2-pyrrolyl)acetonitrile
• 英文别名: tert-butyldimethylsilyloxy(N-methylpyrrol-2-yl)acetonitrile；2-[Tert-butyl(dimethyl)silyl]oxy-2-(1-methylpyrrol-2-yl)acetonitrile
• CAS: 223442-03-3
• 化学式: C₁₃H₂₂N₂OSi
• 分子量: 250.416
• InChiKey: NPXMYOVDTYJOGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-isopropoxy-4-phenylcyclobut-3-ene-1,2-dione 、 tert-butyldimethylsilyloxy(1-methyl-2-pyrrolyl)acetonitrile 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到5-(tert-butyldimethylsiloxy)-4-isopropoxy-6-(1-methyl-2-pyrrolyl)-3-phenyl-2-pyrone
  参考文献：
  名称：

  从环丁二烯和锂化的O-甲硅烷基氰醇一步合成α-吡喃酮。

  摘要：

  DOI：

  10.1021/jo982271m
• 作为产物：
  描述：

  N-甲基-2-吡咯甲醛 在 咪唑 、 Amberlyst-A₂₁ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyldimethylsilyloxy(1-methyl-2-pyrrolyl)acetonitrile
  参考文献：
  名称：

  Asymmetric biocatalytic hydrocyanation of pyrrole carboxaldehydes

  摘要：

  The asymmetric hydrocyanation of pyrrole-2- and -3-carboxaldehydes substituted with either methyl, benzyl or phenyl in the I-position catalyzed by the hydroxynitrile lyases from Hevea brasiliensis (HbHNL) and Prunus amygdalus (PaHNL) is reported. The products could be isolated-after O-sitylation-with moderate to good enantiomeric purity although the carbon, I activity of the substrates was found to be very low, which is supported by quantum-chemical calculations. Structural effects concerning substrate size and regiochemistry are discussed considering docking calculations based on the X-ray crystal structures of the two enzymes. From these calculations one particular amino acid residue (Trp-128) in the active site of HbHNL could be identified, which plays a major role for the appropriate binding of structurally demanding carbonyl compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.095

文献信息

• One-Step Synthesis of Substituted α-Pyrones from Cyclobutenediones and Lithiated <i>O</i>-Silyl Cyanohydrins
  作者：Pamela Mingo、Shijie Zhang、Lanny S. Liebeskind

  DOI：10.1021/jo982271m

  日期：1999.3.1
• Asymmetric biocatalytic hydrocyanation of pyrrole carboxaldehydes
  作者：Thomas Purkarthofer、Karl Gruber、Martin H. Fechter、Herfried Griengl

  DOI：10.1016/j.tet.2005.05.095

  日期：2005.8

  The asymmetric hydrocyanation of pyrrole-2- and -3-carboxaldehydes substituted with either methyl, benzyl or phenyl in the I-position catalyzed by the hydroxynitrile lyases from Hevea brasiliensis (HbHNL) and Prunus amygdalus (PaHNL) is reported. The products could be isolated-after O-sitylation-with moderate to good enantiomeric purity although the carbon, I activity of the substrates was found to be very low, which is supported by quantum-chemical calculations. Structural effects concerning substrate size and regiochemistry are discussed considering docking calculations based on the X-ray crystal structures of the two enzymes. From these calculations one particular amino acid residue (Trp-128) in the active site of HbHNL could be identified, which plays a major role for the appropriate binding of structurally demanding carbonyl compounds. (c) 2005 Elsevier Ltd. All rights reserved.