2-diazo-3-hydroxy-1-indanone | 28164-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-diazo-3-hydroxy-1-indanone
• 英文别名: 2-diazo-3-hydroxyindan-1-one；3-Hydroxy-2-diazo-indanon-(1)；2-diazo-3-hydroxy-3H-inden-1-one
• CAS: 28164-53-6
• 化学式: C₉H₆N₂O₂
• 分子量: 174.159
• InChiKey: PLWHIJXFEBRNLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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-1-indanone 在 硫酸 作用下， 生成 2-diazo-indan-1,3-dione
  参考文献：
  名称：

  Severin,T.; Lerche,H., Chemische Berichte, 1970, vol. 103, p. 2148 - 2151

  摘要：

  DOI：
• 作为产物：
  描述：

  2-diazo-indan-1,3-dione 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 2-diazo-3-hydroxy-1-indanone
  参考文献：
  名称：

  Severin,T.; Lerche,H., Chemische Berichte, 1970, vol. 103, p. 2148 - 2151

  摘要：

  DOI：

文献信息

• Synthesis of 1,3-diketones using .alpha.-diazo ketones and aldehydes in the presence of tin(II) chloride
  作者：Albert Padwa、Susan F. Hornbuckle、Zhijia Zhang、Lin Zhi

  DOI：10.1021/jo00305a029

  日期：1990.8
• 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).
• PADWA, ALBERT;HORNBUCKLE, SUSAN F.;ZHANG, ZHIJIA;ZHI, LIN, J. ORG. CHEM., 55,(1990) N8, C. 5297-5299
  作者：PADWA, ALBERT、HORNBUCKLE, SUSAN F.、ZHANG, ZHIJIA、ZHI, LIN

  DOI：——

  日期：——