2-diazo-3-hydroxy-4,4,6,6-tetramethylcyclohexanone | 81887-88-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-diazo-3-hydroxy-4,4,6,6-tetramethylcyclohexanone
• 英文别名: 2-Diazo-3-hydroxy-4,4,6,6-tetramethyl-1-cyclohexanone；2-Diazo-3-hydroxy-4,4,6,6-tetramethylcyclo-hexanone；6-diazo-5-hydroxy-2,2,4,4-tetramethylcyclohexan-1-one
• CAS: 81887-88-9
• 化学式: C₁₀H₁₆N₂O₂
• 分子量: 196.249
• InChiKey: PVIJOOIGZZKWDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  39.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-diazo-3-hydroxy-4,4,6,6-tetramethylcyclohexanone 以84%的产率得到
  参考文献：
  名称：

  NIKOLAEV, V. A.;ZHDANOVA, O. V.;KOROBITSYNA, I. K., ZH. ORGAN. XIMII, 1982, 18, N 3, 559-572

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Diazo-4,4,6,6-tetramethylcyclohexane-1,3-dione 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以87%的产率得到2-diazo-3-hydroxy-4,4,6,6-tetramethylcyclohexanone
  参考文献：
  名称：

  Nikolaev, V. A.; Zhdanova, O. V.; Korobitsyna, I. K., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 488 - 498

  摘要：

  DOI：

文献信息

• Chemistry of Diazocarbonyl Compounds: XVIII. Synthesis and Spectral Parameters of 1,3-Dialkyl- 3-hydroxy-2-diazoketones
  作者：O. V. Zhdanova、S. M. Korneev、V. A. Nikolaev

  DOI：10.1023/b:rujo.0000034964.50578.fb

  日期：2004.3

  Reduction of the carbonyl groups in cyclic and acyclic 2-diazo-1,3-diketones with sodium tetra-hydridoborate in aqueous-alcoholic medium, followed by hydrolysis of the reaction mixture over wet silica gel and chromatographic purification on neutral aluminum oxide, afforded 1,3-dialkyl-3-hydroxy-2-diazoketones in 58-87% yield. Bulky substituents at the carbonyl group considerably reduce the efficiency of the process, and the reduction of cis- and trans-4,6-di-tert-butyl-2-diazocyclohexane-1,3-diones is characterized by low stereoselectivity (de 40-49%). In the IR spectra of 3-hydroxy-2-diazocyclohexanes, absorption bands corresponding to stretching vibrations of "free" axial hydroxy groups are located at higher frequencies (by 2045 cm(-1)) than those belonging to equatorial hydroxy groups. These parameters may be useful for conformational analysis of cyclic hydroxy diazo ketones. Stabilization of the E conformation of acyclic hydroxy diazo ketones via intramolecular hydrogen bonding is likely to occur only in nonpolar solvents (CCl4, cyclohexane).