N,N-diisopropyl-8-formyl-1-naphthamide | 254756-10-0

• 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-formyl-1-naphthamide
• 英文别名: 8-formyl-N,N-di(propan-2-yl)naphthalene-1-carboxamide
• CAS: 254756-10-0
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: UGBFEPLMGLAEIK-UHFFFAOYSA-N

物化性质

• 沸点：
  457.2±18.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基溴化镁 、 N,N-diisopropyl-8-formyl-1-naphthamide 以 四氢呋喃 为溶剂， 反应 3.5h， 以81%的产率得到(S_a*,1'S*/R*)-N,N-Diisopropyl-8-(1'-hydroxyethyl)-1-naphthamide
  参考文献：
  名称：

  Atropisomeric diastereoisomers from nucleophilic attack on 8-acyl-1-naphthamides

  摘要：

  Ar-CO键的受限旋转意味着带有手性8位取代基的1-萘甲酰胺可能以非对映异构体对的形式存在。这些非对映异构体是通过8-甲酰基-1-萘甲酰胺与有机锂和格氏试剂的反应形成的，对同分非对映异构体具有良好到极好的立体选择性。8-酰基-1-萘甲酰胺的还原也具有同分选择性。产物醇容易发生内酯化反应和消旋化反应，一些明显的非对映选择性可能是热力学控制的结果，而不是动力学控制的结果。

  DOI：

  10.1039/b000670j
• 作为产物：
  描述：

  N,N-二甲基-1-(萘-1-基)甲胺 在 正丁基锂 、 双氧水 、 三氟乙酸酐 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 N,N-diisopropyl-8-formyl-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.
• Atropisomeric diastereoisomers from nucleophilic attack on 8-acyl-1-naphthamides
  作者：Jonathan Clayden、Neil Westlund、Christopher S. Frampton

  DOI：10.1039/b000670j

  日期：——

  Restricted rotation about the Ar–CO bond means that 1-naphthamides bearing chiral 8-substituents may exist as pairs of diastereoisomeric atropisomers. These atropisomers are formed with good to excellent stereoselectivity for the syn-diastereoisomer by the reaction of 8-formyl-1-naphthamides with organolithiums and Grignard reagents. The reduction of 8-acyl-1-naphthamides also proceeds with syn-selectivity. The product alcohols are prone to lactonisation and also to epimerisation, and some of the apparent diastereoselectivities may be the result of thermodynamic, rather than kinetic, control.

  Ar-CO键的受限旋转意味着带有手性8位取代基的1-萘甲酰胺可能以非对映异构体对的形式存在。这些非对映异构体是通过8-甲酰基-1-萘甲酰胺与有机锂和格氏试剂的反应形成的，对同分非对映异构体具有良好到极好的立体选择性。8-酰基-1-萘甲酰胺的还原也具有同分选择性。产物醇容易发生内酯化反应和消旋化反应，一些明显的非对映选择性可能是热力学控制的结果，而不是动力学控制的结果。