3-碘-4-羟基-1,2-萘醌 | 572874-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-碘-4-羟基-1,2-萘醌
• 英文名称: 3-iodo-4-hydroxy-1,2-naphthoquinone
• 英文别名: 2-Hydroxy-3-iodo-1,4-naphthoquinone；4-hydroxy-3-iodonaphthalene-1,2-dione
• CAS: 572874-62-5
• 化学式: C₁₀H₅IO₃
• 分子量: 300.052
• InChiKey: KDAAEHKHRCUSIF-UHFFFAOYSA-N

物化性质

• 熔点：
  169-171 °C
• 沸点：
  383.5±42.0 °C(Predicted)
• 密度：
  2.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-碘-4-羟基-1,2-萘醌 在 sodium hydroxide 作用下， 以100%的产率得到2-hydroxy-3-iodo-1,4-naphthoquinone
  参考文献：
  名称：

  Studies on the Reactivity of Aryliodonium Ylides of 2-Hydroxy-1,4-naphthoquinone:  Reactions with Amines

  摘要：

  Aryliodonium ylides of 2-hydroxy-1,4-naphthoquinone react with amines in refluxing dichloromethane to afford good yields of indanedione 2-carboxamides 5, through a ring-contraction and alpha,alpha'-dioxoketene formation reaction. These amides exist in solution in an unusual enol-amide form. In contrast, the same reactants in a copper-catalyzed reaction afford arylamines and 3-iodo-4-hydroxy-1,2-naphthoquinone.

  DOI：

  10.1021/jo0343679
• 作为产物：
  描述：

  Z,E-3-iodo-4-hydroxy-1[(2-phenylethyl)imino]-2-naphthalenone 在 silica gel 作用下， 生成 2-苯乙胺 、 3-碘-4-羟基-1,2-萘醌
  参考文献：
  名称：

  Studies on the Reactivity of Aryliodonium Ylides of 2-Hydroxy-1,4-naphthoquinone:  Reactions with Amines

  摘要：

  Aryliodonium ylides of 2-hydroxy-1,4-naphthoquinone react with amines in refluxing dichloromethane to afford good yields of indanedione 2-carboxamides 5, through a ring-contraction and alpha,alpha'-dioxoketene formation reaction. These amides exist in solution in an unusual enol-amide form. In contrast, the same reactants in a copper-catalyzed reaction afford arylamines and 3-iodo-4-hydroxy-1,2-naphthoquinone.

  DOI：

  10.1021/jo0343679

文献信息

• A Survey on the Reactivity of Phenyliodonium Ylide of 2-Hydroxy-1,4-Naphthoquinone with Amino Compounds
  作者：Konstantina Spagou、Elizabeth Malamidou-Xenikaki、Spyros Spyroudis

  DOI：10.3390/10010226

  日期：——

  The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed reaction afford mainly the corresponding N-arylo compounds. Arylhydrazines are mainly oxidized by the ylide and arylation occurs only in a low yield.

  2-羟基-1,4-萘醌的苯基碘鎓叶立德与氨基酯、脲、氨基醇和氨基酚在回流的二氯甲烷中反应，以良好的产率得到吲哚二酮2-酰胺化合物，其在溶液中以烯醇酰胺形式存在。在铜催化的反应中，同样的反应物主要得到相应的N-芳基化合物。芳基肼主要被叶立德氧化，芳基化仅在低产率下发生。