1.5-dinitro-2-hydroxy-naphthalene | 80651-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1.5-dinitro-2-hydroxy-naphthalene
• 英文别名: 1.5-Dinitro-2-hydroxy-naphthalin；1,5-dinitro-2-naphthalenol；1,5-Dinitronaphthalen-2-ol
• CAS: 80651-00-9
• 化学式: C₁₀H₆N₂O₅
• 分子量: 234.168
• InChiKey: FKKAUKDPTFKSHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,5-二硝基萘 在 sodium hydroxide 、 过氧化氢异丙苯 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以5%的产率得到1.5-dinitro-2-hydroxy-naphthalene
  参考文献：
  名称：

  Specific para-hydroxylation of nitronaphthalenes with cumene hydroperoxide in basic aqueous media

  摘要：

  A synthetic method for specific para-hydroxylation of nitroarenes has been developed. The reaction of nitronaphthalenes with cumeme hydroperoxide in basic aqueous media produces exclusively pam-hydroxy nitronaphthalenes in good yield. The selectivity of ortho and para hydroxylation is mediated by water content. The rationale for water-controlled orientation of hydroxylation has been briefly discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00415-9

文献信息

• Hydroxylation of Nitroarenes with Alkyl Hydroperoxide Anions via Vicarious Nucleophilic Substitution of Hydrogen
  作者：Mieczysław Makosza、Krzysztof Sienkiewicz

  DOI：10.1021/jo970726m

  日期：1998.6.1

  Carbo- -and heterocyclic nitroarenes react with anions of tert-butyl and cumyl hydroperoxides in the presence of strong bases to form substituted o- and p-nitrophenols. The reaction usually proceeds in high yields and is of practical value as a method of synthesis and manufacturing of nitrophenols. Orientation of the hydroxylation can be controlled to a substantial extent by selection of the proper conditions. Basic mechanistic features of this process were clarified.
• Malykhin; Shteingarts, Russian Journal of Organic Chemistry, 1997, vol. 33, # 5, p. 636 - 643
  作者：Malykhin、Shteingarts

  DOI：——

  日期：——
• 79. The nitration of α- and β-naphthols
  作者：F. Bell

  DOI：10.1039/jr9330000286

  日期：——
• Malykhin, E.V.; Shtark, A.A.; Shteingarts, V.D., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 1661 - 1666
  作者：Malykhin, E.V.、Shtark, A.A.、Shteingarts, V.D.

  DOI：——

  日期：——
• Malykhin, E. V.; Shteingarts, V. D., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 11, p. 2146 - 2152
  作者：Malykhin, E. V.、Shteingarts, V. D.

  DOI：——

  日期：——