N-(1-methylethyl)-N-[(1S)-1-phenylethyl]-1-naphthalenecarboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(1-methylethyl)-N-[(1S)-1-phenylethyl]-1-naphthalenecarboxamide
• 英文别名: N-[(1S)-1-phenylethyl]-N-propan-2-ylnaphthalene-1-carboxamide
• 化学式: C₂₂H₂₃NO
• 分子量: 317.431
• InChiKey: XJQJIQFWGGYFIX-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(1-methylethyl)-N-[(1S)-1-phenylethyl]-1-naphthalenecarboxamide 在 N,N-二甲基丙烯基脲 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以61%的产率得到(3R,3aR,9bR)-2-Isopropyl-3-methyl-3-phenyl-2,3,3a,9b-tetrahydro-benzo[e]isoindol-1-one
  参考文献：
  名称：

  Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations

  摘要：

  Dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N-substituents (such as alpha-methylbenzyl) proceeds with overall retention of configuration at the newly formed tetrasubstituted chiral centre. The cyclisation is stereospecific overall, with the configuration of the starting trisubstituted stereogenic centre controlling the stereochemistry of the product. Highly substituted pyrrolidinone rings may be formed as single enantiomers from enantiomerically pure starting materials. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01765-7
• 作为产物：
  描述：

  (S)-N-isopropyl-1-phenylethylamine 、 1-萘甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以85%的产率得到N-(1-methylethyl)-N-[(1S)-1-phenylethyl]-1-naphthalenecarboxamide
  参考文献：
  名称：

  Stereodynamics of Bond Rotation in Tertiary Aromatic Amides

  摘要：

  The degree to which the rotations about the C-N and Ar-CO bonds of aromatic amides occur in a concerted manner was investigated by a variety of NMR and kinetic techniques. Otherwise complex kinetic analyses were simplified by exploiting symmetry and asymmetry in the N-substituents of amides. In 2-unsubstituted 1-naphthamides bearing branched N-substituents, most conformational changes about the amide group were by correlated rotation, though uncorrelated Ar-CO rotation also occurred to some extent. In 2-substituted 1-naphthamides, correlated rotation accounted for all of the Ar-CO rotations, though a significant amount of uncorrelated C-N rotation also occurred. Naphthamides bearing branched N-substituents thus turn out to be efficient molecular gears.

  DOI：

  10.1002/1521-3765(20020315)8:6<1279::aid-chem1279>3.0.co;2-7

文献信息

• Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations
  作者：Ryan A. Bragg、Jonathan Clayden

  DOI：10.1016/s0040-4039(99)01765-7

  日期：1999.11

  Dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N-substituents (such as alpha-methylbenzyl) proceeds with overall retention of configuration at the newly formed tetrasubstituted chiral centre. The cyclisation is stereospecific overall, with the configuration of the starting trisubstituted stereogenic centre controlling the stereochemistry of the product. Highly substituted pyrrolidinone rings may be formed as single enantiomers from enantiomerically pure starting materials. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Stereodynamics of Bond Rotation in Tertiary Aromatic Amides
  作者：Ryan A. Bragg、Jonathan Clayden、Gareth A. Morris、Jennifer H. Pink

  DOI：10.1002/1521-3765(20020315)8:6<1279::aid-chem1279>3.0.co;2-7

  日期：2002.3.15

  The degree to which the rotations about the C-N and Ar-CO bonds of aromatic amides occur in a concerted manner was investigated by a variety of NMR and kinetic techniques. Otherwise complex kinetic analyses were simplified by exploiting symmetry and asymmetry in the N-substituents of amides. In 2-unsubstituted 1-naphthamides bearing branched N-substituents, most conformational changes about the amide group were by correlated rotation, though uncorrelated Ar-CO rotation also occurred to some extent. In 2-substituted 1-naphthamides, correlated rotation accounted for all of the Ar-CO rotations, though a significant amount of uncorrelated C-N rotation also occurred. Naphthamides bearing branched N-substituents thus turn out to be efficient molecular gears.