(S)-tert-butyl 1-(4-oxo-3,4-dihydroquinazolin-2-yl)-2-phenylethylcarbamate | 1312716-45-2

• 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: (S)-tert-butyl 1-(4-oxo-3,4-dihydroquinazolin-2-yl)-2-phenylethylcarbamate
• CAS: 1312716-45-2
• 化学式: C₂₁H₂₃N₃O₃
• 分子量: 365.432
• InChiKey: UVFAVYSUUWLSPL-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.08
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 1-(4-oxo-3,4-dihydroquinazolin-2-yl)-2-phenylethylcarbamate 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 苯 为溶剂， 反应 0.5h， 以95%的产率得到(S)-tert-butyl 1-(4-chloroquinazolin-2-yl)-2-phenylethylcarbamate
  参考文献：
  名称：

  Synthesis and asymmetric catalytic activity of (1S,1′S)-4,4′-biquinazoline-based primary amines

  摘要：

  A series of (1S,1'S)-4,4'-biquinazoline-based primary amines were prepared from natural amino acids via a six-step reaction sequence of protection and condensation followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection. These novel amines were screened for the asymmetric ethylation of aryl aldehydes to yield alcohols with an (S)-configuration with enantiomeric excesses (ee) varying from 2% to 95%. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.009
• 作为产物：
  描述：

  (S)-tert-butyl 1-(2-carbamoylphenylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.58h， 以98%的产率得到(S)-tert-butyl 1-(4-oxo-3,4-dihydroquinazolin-2-yl)-2-phenylethylcarbamate
  参考文献：
  名称：

  Synthesis and asymmetric catalytic activity of (1S,1′S)-4,4′-biquinazoline-based primary amines

  摘要：

  A series of (1S,1'S)-4,4'-biquinazoline-based primary amines were prepared from natural amino acids via a six-step reaction sequence of protection and condensation followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection. These novel amines were screened for the asymmetric ethylation of aryl aldehydes to yield alcohols with an (S)-configuration with enantiomeric excesses (ee) varying from 2% to 95%. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.009

文献信息

• Structure-based design of novel dihydroisoquinoline BACE-1 inhibitors that do not engage the catalytic aspartates
  作者：Simeon Bowers、Ying-zi Xu、Shendong Yuan、Gary D. Probst、Roy K. Hom、Wayman Chan、Andrei W. Konradi、Hing L. Sham、Yong L. Zhu、Paul Beroza、Hu Pan、Eric Brecht、Nanhua Yao、Julie Lougheed、Danny Tam、Zhao Ren、Lany Ruslim、Michael P. Bova、Dean R. Artis

  DOI：10.1016/j.bmcl.2013.01.103

  日期：2013.4

  The structure-activity relationship of a series of dihydroisoquinoline BACE-1 inhibitors is described. Application of structure-based design to screening hit 1 yielded sub-micromolar inhibitors. Replacement of the carboxylic acid of 1 was guided by X-ray crystallography, which allowed the replacement of a key water-mediated hydrogen bond. This work culminated in compounds such as 31, which possess good BACE-1 potency, excellent permeability and a low P-gp efflux ratio. (C) 2013 Elsevier Ltd. All rights reserved.