rac-2-hydroxy-2-methyl-4-oxo-4-phenyl-butyronitrile | 78731-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-2-hydroxy-2-methyl-4-oxo-4-phenyl-butyronitrile
• 英文别名: 2-hydroxy-2-methyl-4-oxo-4-phenylbutyronitrile；2-Hydroxy-2-methyl-4-oxo-4-phenylbutanenitrile
• CAS: 78731-92-7
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: SWJWJVYTYFKAKT-UHFFFAOYSA-N

物化性质

• 沸点：
  402.3±35.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-2-hydroxy-2-methyl-4-oxo-4-phenyl-butyronitrile 在 base 作用下， 以 水 为溶剂， 生成 1-苯基-1,3-丁二酮
  参考文献：
  名称：

  The synthesis of selectively protected β-diketones and α-ketoaldehydes

  摘要：

  DOI：

  10.1016/s0040-4039(01)90266-7
• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 丙酮腈 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以73%的产率得到rac-2-hydroxy-2-methyl-4-oxo-4-phenyl-butyronitrile
  参考文献：
  名称：

  Facile Synthesis of a “Ready to Use” Precursor of Porphobilinogen and Its Amino Acid Derivatives

  摘要：

  [GRAPHICS]A practical synthesis of porphobilinogen based on the biosynthetic mechanism is described. The crossed Mukayiama. aldol reaction is the key step creating the central carbon-carbon bond between the two protected forms of 5-aminolevulinic acids. The optimized sequence gives a crystalline, storable precursor, which can be transformed in high yield into porphobilinogen and bioconjugates thereof. The enzymatic hydrolysis of the precursor produces porphobilinogen in quantitative yield.

  DOI：

  10.1021/jo702319n

文献信息

• KRAUS G. A.; SHIMAGAKI M., TETRAHEDRON LETT., 1981, 22, NO 13, 1171-1174
  作者：KRAUS G. A.、 SHIMAGAKI M.

  DOI：——

  日期：——
• Facile Synthesis of a “Ready to Use” Precursor of Porphobilinogen and Its Amino Acid Derivatives
  作者：Carole Pissot Soldermann、Ramakrishnan Vallinayagam、Manuel Tzouros、Reinhard Neier

  DOI：10.1021/jo702319n

  日期：2008.1.1

  [GRAPHICS]A practical synthesis of porphobilinogen based on the biosynthetic mechanism is described. The crossed Mukayiama. aldol reaction is the key step creating the central carbon-carbon bond between the two protected forms of 5-aminolevulinic acids. The optimized sequence gives a crystalline, storable precursor, which can be transformed in high yield into porphobilinogen and bioconjugates thereof. The enzymatic hydrolysis of the precursor produces porphobilinogen in quantitative yield.
• The synthesis of selectively protected β-diketones and α-ketoaldehydes
  作者：George A. Kraus、Masayuki Shimagaki

  DOI：10.1016/s0040-4039(01)90266-7

  日期：1981.1