Z,E-3-iodo-4-hydroxy-1[(2-phenylethyl)imino]-2-naphthalenone | 571166-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Z,E-3-iodo-4-hydroxy-1[(2-phenylethyl)imino]-2-naphthalenone
• 英文别名: 4-Hydroxy-3-iodo-1-(2-phenylethylimino)naphthalen-2-one
• CAS: 571166-63-7
• 化学式: C₁₈H₁₄INO₂
• 分子量: 403.219
• InChiKey: VXDIHQVOTFMBJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Z,E-3-iodo-4-hydroxy-1[(2-phenylethyl)imino]-2-naphthalenone 在 silica gel 作用下， 以 二氯甲烷 为溶剂， 生成 1,3-dioxo-N-(2'-phenylethyl)-2-indancarboxamide
  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：

  2-苯乙胺 、 碘正离子,苯基-,3,4-二氢-1,3,4-三羰基-2(1H)-萘自由基负离子 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到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

• Studies on the Reactivity of Aryliodonium Ylides of 2-Hydroxy-1,4-naphthoquinone:  Reactions with Amines
  作者：Elizabeth Malamidou-Xenikaki、Spyros Spyroudis、Maria Tsanakopoulou

  DOI：10.1021/jo0343679

  日期：2003.7.1

  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.