o-(2-phenylallyl)-N,N-diisopropyl-1-naphthamide | 296237-55-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: o-(2-phenylallyl)-N,N-diisopropyl-1-naphthamide
• 英文别名: 2-(2-phenylprop-2-enyl)-N,N-di(propan-2-yl)naphthalene-1-carboxamide
• CAS: 296237-55-3
• 化学式: C₂₆H₂₉NO
• 分子量: 371.522
• InChiKey: JEUYCSQOCBIUEX-UHFFFAOYSA-N

物化性质

• 沸点：
  532.6±29.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  o-(2-phenylallyl)-N,N-diisopropyl-1-naphthamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以60%的产率得到N,N-diisopropyl-1-naphthamide
  参考文献：
  名称：

  New Synthesis of Vaulted Biaryl Ligands via the Snieckus Phenol Synthesis

  摘要：

  In an effort to develop a synthesis of the VAPOL ligand that avoids the use of a chromium carbene complex, a route vias examined that involved the annulation of a naphthalene carboxamide via the method of Snieckus. The latter derivatives could be converted in a two-step sequence to 2-phenyl-4-phenanthrols in 6D-72% overall yields. The utility of this method for the synthesis of VAPOL derivatives is demonstrated in the synthesis of (S)-7,7'-dimethyl-VAPOL.

  DOI：

  10.1021/ol047852e
• 作为产物：
  描述：

  1-萘甲酸 在 sodium hydroxide 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 苯 为溶剂， 反应 2.5h， 生成 o-(2-phenylallyl)-N,N-diisopropyl-1-naphthamide
  参考文献：
  名称：

  New Synthesis of Vaulted Biaryl Ligands via the Snieckus Phenol Synthesis

  摘要：

  In an effort to develop a synthesis of the VAPOL ligand that avoids the use of a chromium carbene complex, a route vias examined that involved the annulation of a naphthalene carboxamide via the method of Snieckus. The latter derivatives could be converted in a two-step sequence to 2-phenyl-4-phenanthrols in 6D-72% overall yields. The utility of this method for the synthesis of VAPOL derivatives is demonstrated in the synthesis of (S)-7,7'-dimethyl-VAPOL.

  DOI：

  10.1021/ol047852e

文献信息

• [EN] SYNTHESIS OF VAPOL LIGANDS<br/>[FR] SYNTHESE DE LIGANDS VAPOL
  申请人：ARCH DEV CORP

  公开号：WO2000056691A1

  公开（公告）日：2000-09-28

  The present invention relates to a process for making the chiral ligand 2,2'-diphenyl-[3,3'-biphenanthrene]-4,4'-diol, also known as VAPOL, as well as other novel chiral ligands.
• New Synthesis of Vaulted Biaryl Ligands via the Snieckus Phenol Synthesis
  作者：Su Yu、Constantinos Rabalakos、William D. Mitchell、William D. Wulff

  DOI：10.1021/ol047852e

  日期：2005.2.1

  In an effort to develop a synthesis of the VAPOL ligand that avoids the use of a chromium carbene complex, a route vias examined that involved the annulation of a naphthalene carboxamide via the method of Snieckus. The latter derivatives could be converted in a two-step sequence to 2-phenyl-4-phenanthrols in 6D-72% overall yields. The utility of this method for the synthesis of VAPOL derivatives is demonstrated in the synthesis of (S)-7,7'-dimethyl-VAPOL.