rac-2-hydroxy-2-(2-oxocyclohexyl)-propionitrile | 78747-28-1

• 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-(2-oxocyclohexyl)-propionitrile
• 英文别名: 2-Hydroxy-2-(2-oxocyclohexyl)propanenitrile
• CAS: 78747-28-1
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: PHARTHCGMDSFBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  丙酮腈 、 1-环己烯氧基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以64%的产率得到rac-2-hydroxy-2-(2-oxocyclohexyl)-propionitrile
  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

• 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
• 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.