rac-2-tert-butyl-2-hydroxy-4-oxo-4-phenyl-butyronitrile | 1006610-14-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-2-tert-butyl-2-hydroxy-4-oxo-4-phenyl-butyronitrile
• 英文别名: 2-Hydroxy-3,3-dimethyl-2-phenacylbutanenitrile
• CAS: 1006610-14-5
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: CWLGAJVEZOWFBK-UHFFFAOYSA-N

物化性质

• 沸点：
  415.0±35.0 °C(predicted)
• 密度：
  1.096±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 特戊酰氰 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以15%的产率得到rac-2-tert-butyl-2-hydroxy-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

• 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.