N-benzyl-N-[(1S)-1-phenylethyl]-1-naphthamide | 255916-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-benzyl-N-[(1S)-1-phenylethyl]-1-naphthamide
• 英文别名: N-benzyl-N-[(1S)-1-phenylethyl]naphthalene-1-carboxamide
• CAS: 255916-68-8
• 化学式: C₂₆H₂₃NO
• 分子量: 365.475
• InChiKey: FDSZHMPRUWWIOL-FQEVSTJZSA-N

物化性质

• 沸点：
  570.1±39.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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-benzyl-N-[(1S)-1-phenylethyl]-1-naphthamide 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 20.0h， 生成 (3S,3aS,9bS)-3-Methyl-3-phenyl-2-((S)-1-phenyl-ethyl)-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-苄基-1-苯基-乙胺 、 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39%的产率得到N-benzyl-N-[(1S)-1-phenylethyl]-1-naphthamide
  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

• Dearomatising cyclisation of lithiated 1-naphthamides with a phenylglycinol-derived chiral auxiliary: asymmetric synthesis of an arylkainoid and a kainoid-like pyroglutamate
  作者：Ryan A Bragg、Jonathan Clayden、Michael Bladon、Osamu Ichihara

  DOI：10.1016/s0040-4039(01)00502-0

  日期：2001.5

  N-benzylphenylglycinols undergo a diastereoselective dearomatising cyclisation on treatment with t-BuLi and DMPU or HMPA. A new pyrrolidinone ring is formed bearing three new stereogenic centers of defined absolute stereochemistry. Removal of the phenylglycinol auxiliary gives enantiomerically pure substituted lactams exhibiting the stereochemistry of the kainoids. These may be converted to kainoid-like pyroglutamates

  在用t -BuLi和DMPU或HMPA处理后，N-苄基苯基甘氨醇的1-萘酰胺经历非对映选择性脱芳环化。形成带有定义的绝对立体化学的三个新的立体异构中心的新的吡咯烷酮环。除去苯基甘氨醇助剂，得到对映体纯的取代内酰胺，其表现出类胡萝卜素的立体化学。这些可以被转化成类卡因碱样的焦谷氨酸盐，或者可替代地，使用先前论文的方法，被转化为丙烯醛酸的类似物。
• ‘meso-Selective’ functionalisation of N-benzyl-α-methylbenzylamine derivatives by α-lithiation and alkylation
  作者：Ryan A Bragg、Jonathan Clayden、Christel J Menet

  DOI：10.1016/s0040-4039(02)00154-5

  日期：2002.3

  Lithiation and methylation of amide and carbamate derivatives of alpha-methylbenzylamine proceeds with high diastereoselectivity in favour of meso bis-alpha-methylbenzylamine derivatives, Carboxylation of the intermediate organolithium is also diastereoselective, and with N-Boc p-methoxy-alpha-methylbenzylamine as starting material, oxidative cleavage provides a new asymmetric route to phenylglycine. Other electrophiles give a range of stereochemical outcomes, apparently depending on the stereospecificity of their reactions with a pair of diastereoisomeric organolithiums of low to moderate configurational stability. (C) 2002 Elsevier Science Ltd. All rights reserved.