2-重氮基-3-羟基-1-环己酮 | 81902-29-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-重氮基-3-羟基-1-环己酮
• 英文名称: 2-Diazo-3-hydroxy-1-cyclohexanone
• 英文别名: 2-diazo-3-hydroxycyclohexanone；3-Hydroxy-2-diazocyclohexanone；2-diazo-3-hydroxycyclohexan-1-one
• CAS: 81902-29-6
• 化学式: C₆H₈N₂O₂
• 分子量: 140.142
• InChiKey: AEWYEUGJAIWUBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-重氮基-3-羟基-1-环己酮 以1%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-diazocyclohexane-1,3-dione 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.83h， 以65%的产率得到2-重氮基-3-羟基-1-环己酮
  参考文献：
  名称：

  Chemistry of Diazocarbonyl Compounds: XVIII. Synthesis and Spectral Parameters of 1,3-Dialkyl- 3-hydroxy-2-diazoketones

  摘要：

  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).

  DOI：

  10.1023/b:rujo.0000034964.50578.fb

文献信息

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

  DOI：——

  日期：——