α,β-dihydroxy-isobutyronitrile | 114983-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α,β-dihydroxy-isobutyronitrile
• 英文别名: α,β-Dihydroxy-isobutyronitril；(+/-)-2,3-Dihydroxy-2-methyl-propionitril；2,3-Dihydroxy-2-methylpropanenitrile；2,3-dihydroxy-2-methylpropanenitrile
• CAS: 114983-36-7
• 化学式: C₄H₇NO₂
• 分子量: 101.105
• InChiKey: LVWXFBPEZPFFAI-UHFFFAOYSA-N

物化性质

• 沸点：
  100 °C(Press: 19 Torr)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基丙烯腈 在 Fe(tripicolylamine)(trifluoromethanesulphonate)₂ 、 双氧水 作用下， 以 乙腈 为溶剂， 生成 α,β-dihydroxy-isobutyronitrile
  参考文献：
  名称：

  Iron-Catalyzed Olefin cis-Dihydroxylation by H₂O₂:  Electrophilic versus Nucleophilic Mechanisms

  摘要：

  Previous studies have classified a series of nonheme iron catalysts for olefin cis-dihydroxylation by H2O2 into two groups. Complex 1, [(TPA)Fe(OTf)2], representative of Class A catalysts, forms a low-spin FeIII-OOH intermediate that gives rise to a high-valent FeV(=O)OH oxidant. The preference of this catalyst for electron-rich olefins demonstrates its electrophilic character. On the other hand, complex 2, [(6-Me3-TPA)Fe(OTf)2], representative of Class B catalysts, prefers instead to oxidize electron-deficient olefins, suggesting an oxidant with nucleophilic character. It is suggested that such a nucleophilic oxidant may be the high-spin FeIII-OOH intermediate derived from 2 or the FeIV(=O)(*OH) species derived therefrom.

  DOI：

  10.1021/ja029863d

文献信息

• Boileau et al., Bulletin de la Societe Chimique de France, 1957, p. 338,341
  作者：Boileau et al.

  DOI：——

  日期：——
• Iron-Catalyzed Olefin <i>cis</i>-Dihydroxylation by H₂O₂:  Electrophilic versus Nucleophilic Mechanisms
  作者：Megumi Fujita、Miquel Costas、Lawrence Que

  DOI：10.1021/ja029863d

  日期：2003.8.1

  Previous studies have classified a series of nonheme iron catalysts for olefin cis-dihydroxylation by H2O2 into two groups. Complex 1, [(TPA)Fe(OTf)2], representative of Class A catalysts, forms a low-spin FeIII-OOH intermediate that gives rise to a high-valent FeV(=O)OH oxidant. The preference of this catalyst for electron-rich olefins demonstrates its electrophilic character. On the other hand, complex 2, [(6-Me3-TPA)Fe(OTf)2], representative of Class B catalysts, prefers instead to oxidize electron-deficient olefins, suggesting an oxidant with nucleophilic character. It is suggested that such a nucleophilic oxidant may be the high-spin FeIII-OOH intermediate derived from 2 or the FeIV(=O)(*OH) species derived therefrom.