N,N-diisopropyl-8-[(dimethylamino)methyl]-1-naphthamide | 215438-67-8

• 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)methyl]-1-naphthamide
• 英文别名: 8-[(dimethylamino)methyl]-N,N-di(propan-2-yl)naphthalene-1-carboxamide
• CAS: 215438-67-8
• 化学式: C₂₀H₂₈N₂O
• 分子量: 312.455
• InChiKey: QUEYRXALGIJABX-UHFFFAOYSA-N

物化性质

• 沸点：
  443.6±20.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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-diisopropyl-8-[(dimethylamino)methyl]-1-naphthamide 在 双氧水 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 N,N-diisopropyl-8-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：

  二异丙基甲胺酰氯 、 N,N-二甲基-1-(萘-1-基)甲胺 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以63%的产率得到N,N-diisopropyl-8-[(dimethylamino)methyl]-1-naphthamide
  参考文献：
  名称：

  Diastereoisomeric atropisomers of peri-substituted naphthamides: synthesis, stereoselectivity and stability

  摘要：

  8-Formyl-1-naphthamides can be made by perilithiation of 1-(dimethylaminomethyl)-naphthalene, quenching the organolithium with a carbamoyl chloride and subjecting the product amine to a Polonovski reaction. The naphthamides react stereoselectively with nucleophiles to give predominantly the syn atropisomers of the product alcohols. Oxidation gives ketones which also give mainly the syn atropisonner on reduction. The rate of thermal epimerisation of the products is high relative to 2-substituted 1-naphthamides: the barrier to Ar-CO rotation is ca. 90 kJ mol(-1). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01644-5

文献信息

• Diastereoisomeric atropisomers of peri-substituted naphthamides: synthesis, stereoselectivity and stability
  作者：Jonathan Clayden、Neil Westlund、Francis X. Wilson

  DOI：10.1016/s0040-4039(99)01644-5

  日期：1999.11

  8-Formyl-1-naphthamides can be made by perilithiation of 1-(dimethylaminomethyl)-naphthalene, quenching the organolithium with a carbamoyl chloride and subjecting the product amine to a Polonovski reaction. The naphthamides react stereoselectively with nucleophiles to give predominantly the syn atropisomers of the product alcohols. Oxidation gives ketones which also give mainly the syn atropisonner on reduction. The rate of thermal epimerisation of the products is high relative to 2-substituted 1-naphthamides: the barrier to Ar-CO rotation is ca. 90 kJ mol(-1). (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.