N,N-diisopropyl-8-(dimethylamino)-naphthamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-diisopropyl-8-(dimethylamino)-naphthamide
• 英文别名: 8-(dimethylamino)-N,N-di(propan-2-yl)naphthalene-1-carboxamide
• 化学式: C₁₉H₂₆N₂O
• 分子量: 298.428
• InChiKey: COAWCAQFXZENTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺 、 N,N-diisopropyl-8-(dimethylamino)-naphthamide 在 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以86%的产率得到N,N-diisopropyl-8-(dimethylamino)-2-formyl-1-naphthamide
  参考文献：
  名称：

  Perilithiation and the synthesis of 8-substituted-1-naphthamides

  摘要：

  Attempted perilithiation of 1-naphthamides with their 2-positions blocked leads only to nucleophilic attack on the aromatic ring, but perilithiation of naphthalenes bearing l-substituents such as -NMe2 or -CH2NMe2 allows the synthesis of 8-substituted-1-naphthamides. The 8-CH2NMe2 substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic anhydride as a starting material. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00881-9
• 作为产物：
  描述：

  N,N-二甲基-1-萘胺 、 二异丙基甲胺酰氯 在 叔丁基锂 作用下， 以 正己烷 、 正戊烷 为溶剂， 反应 29.0h， 以75%的产率得到N,N-diisopropyl-8-(dimethylamino)-naphthamide
  参考文献：
  名称：

  Perilithiation and the synthesis of 8-substituted-1-naphthamides

  摘要：

  Attempted perilithiation of 1-naphthamides with their 2-positions blocked leads only to nucleophilic attack on the aromatic ring, but perilithiation of naphthalenes bearing l-substituents such as -NMe2 or -CH2NMe2 allows the synthesis of 8-substituted-1-naphthamides. The 8-CH2NMe2 substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic anhydride as a starting material. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00881-9

文献信息

• Perilithiation and the synthesis of 8-substituted-1-naphthamides
  作者：Jonathan Clayden、Christopher S. Frampton、Catherine McCarthy、Neil Westlund

  DOI：10.1016/s0040-4020(99)00881-9

  日期：1999.12

  Attempted perilithiation of 1-naphthamides with their 2-positions blocked leads only to nucleophilic attack on the aromatic ring, but perilithiation of naphthalenes bearing l-substituents such as -NMe2 or -CH2NMe2 allows the synthesis of 8-substituted-1-naphthamides. The 8-CH2NMe2 substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic anhydride as a starting material. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.