Naphthalene-2-carboxylic acid benzyl-(1-methyl-1-phenyl-ethyl)-amide | 321984-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Naphthalene-2-carboxylic acid benzyl-(1-methyl-1-phenyl-ethyl)-amide
• 英文别名: N-benzyl-N-(2-phenylpropan-2-yl)naphthalene-2-carboxamide
• CAS: 321984-80-9
• 化学式: C₂₇H₂₅NO
• 分子量: 379.502
• InChiKey: OGRFMVBJZPMFJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  Naphthalene-2-carboxylic acid benzyl-(1-methyl-1-phenyl-ethyl)-amide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以98%的产率得到[3(RS),3a(SR),7a(SR)]-2-(1-methyl-1-phenylethyl)-1-phenyl-2,3,3a,9b-tetrahydro-1H-benzo[e]isoindol-3-one
  参考文献：
  名称：

  Dearomatizing Anionic Cyclization of Substituted N-Cumyl-N-benzyl- benzamides on Treatment with LDA:  Synthesis of Partially Saturated Substituted Isoindolones

  摘要：

  [GRAPHICS]On treatment with LDA, substituted N-benzylbenzamides (including those bearing electron withdrawing, electron-donating, or conjugating groups) become lithiated and cyclize to give, after aqueous quench, a range of partially saturated isoindolones as single regio- and stereoisomers, In general, the isoindolones resist rearomatization. Reaction of N-cumyl-N-benzylbenzamides leads to cyclized products which may be deprotected to give N-unsubstituted isoindolones.

  DOI：

  10.1021/ol006786n
• 作为产物：
  描述：

  N-benzylcumylamine 、 2-萘甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 Naphthalene-2-carboxylic acid benzyl-(1-methyl-1-phenyl-ethyl)-amide
  参考文献：
  名称：

  Dearomatizing Anionic Cyclization of Substituted N-Cumyl-N-benzyl- benzamides on Treatment with LDA:  Synthesis of Partially Saturated Substituted Isoindolones

  摘要：

  [GRAPHICS]On treatment with LDA, substituted N-benzylbenzamides (including those bearing electron withdrawing, electron-donating, or conjugating groups) become lithiated and cyclize to give, after aqueous quench, a range of partially saturated isoindolones as single regio- and stereoisomers, In general, the isoindolones resist rearomatization. Reaction of N-cumyl-N-benzylbenzamides leads to cyclized products which may be deprotected to give N-unsubstituted isoindolones.

  DOI：

  10.1021/ol006786n

文献信息

• Dearomatizing Anionic Cyclization of Substituted <i>N</i>-Cumyl-<i>N</i>-benzyl- benzamides on Treatment with LDA:  Synthesis of Partially Saturated Substituted Isoindolones
  作者：Jonathan Clayden、Christel J. Menet、Darren J. Mansfield

  DOI：10.1021/ol006786n

  日期：2000.12.1

  [GRAPHICS]On treatment with LDA, substituted N-benzylbenzamides (including those bearing electron withdrawing, electron-donating, or conjugating groups) become lithiated and cyclize to give, after aqueous quench, a range of partially saturated isoindolones as single regio- and stereoisomers, In general, the isoindolones resist rearomatization. Reaction of N-cumyl-N-benzylbenzamides leads to cyclized products which may be deprotected to give N-unsubstituted isoindolones.