6-Chloro-4-cyclopropyl-1-(2,6-dichlorobenzyl)quinazolin-2(1H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-Chloro-4-cyclopropyl-1-(2,6-dichlorobenzyl)quinazolin-2(1H)-one
• 英文别名: 6-Chloro-4-cyclopropyl-1-[(2,6-dichlorophenyl)methyl]quinazolin-2-one
• 化学式: C₁₈H₁₃Cl₃N₂O
• 分子量: 379.673
• InChiKey: ATURZYQHDHIYNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-乙炔基吡啶 、 6-Chloro-4-cyclopropyl-1-(2,6-dichlorobenzyl)quinazolin-2(1H)-one 在 正丁基锂 、 奎宁 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (S)-6-Chloro-4-cyclopropyl-3,4-dihydro-1-(2,6-dichlorobenzyl)-4-<2-(2-pyridyl)ethyn-1-yl>quinazolin-2(1H)-one 、 (R)-6-Chloro-4-cyclopropyl-3,4-dihydro-1-(2,6-dichlorobenzyl)-4-<2-(2-pyridyl)ethyn-1-yl>quinazolin-2(1H)-one
  参考文献：
  名称：

  Lithium Alkoxides of Cinchona Alkaloids as Chiral Controllers for Enantioselective Acetylide Addition to Cyclic N-Acyl Ketimines

  摘要：

  Highly enantioselective acetylide addition to cyclic N-acyl ketimines 1 can be carried out using the lithium alkoxide of quinine as a stoichiometric chiral additive. Quinidine can be used to give the opposite enantiomer. Optimization of temperature is critical, with low or high temperatures reducing selectivity. Using the bulky 9-anthrylmethyl protecting group at a distal position on the imine, a 97% ee was achieved and applied to the asymmetric synthesis of HIV reverse transcriptase inhibitor 3.

  DOI：

  10.1021/jo00111a016
• 作为产物：
  描述：

  2,6-二氯苄基溴 、 6-氯-4-环丙基-2(1h)-喹唑啉酮 在 sodium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以60%的产率得到6-Chloro-4-cyclopropyl-1-(2,6-dichlorobenzyl)quinazolin-2(1H)-one
  参考文献：
  名称：

  Lithium Alkoxides of Cinchona Alkaloids as Chiral Controllers for Enantioselective Acetylide Addition to Cyclic N-Acyl Ketimines

  摘要：

  Highly enantioselective acetylide addition to cyclic N-acyl ketimines 1 can be carried out using the lithium alkoxide of quinine as a stoichiometric chiral additive. Quinidine can be used to give the opposite enantiomer. Optimization of temperature is critical, with low or high temperatures reducing selectivity. Using the bulky 9-anthrylmethyl protecting group at a distal position on the imine, a 97% ee was achieved and applied to the asymmetric synthesis of HIV reverse transcriptase inhibitor 3.

  DOI：

  10.1021/jo00111a016

文献信息

• Lithium Alkoxides of Cinchona Alkaloids as Chiral Controllers for Enantioselective Acetylide Addition to Cyclic N-Acyl Ketimines
  作者：Mark A. Huffman、Nobuyoshi Yasuda、Ann E. DeCamp、Edward J. J. Grabowski

  DOI：10.1021/jo00111a016

  日期：1995.3

  Highly enantioselective acetylide addition to cyclic N-acyl ketimines 1 can be carried out using the lithium alkoxide of quinine as a stoichiometric chiral additive. Quinidine can be used to give the opposite enantiomer. Optimization of temperature is critical, with low or high temperatures reducing selectivity. Using the bulky 9-anthrylmethyl protecting group at a distal position on the imine, a 97% ee was achieved and applied to the asymmetric synthesis of HIV reverse transcriptase inhibitor 3.