tert-butyl (1S,1'S)-1,1'-(4,4'-biquinazoline-2,2'-diyl)bis(2-methylpropane-1,1-diyl)dicarbamate | 1312716-51-0

• 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: tert-butyl (1S,1'S)-1,1'-(4,4'-biquinazoline-2,2'-diyl)bis(2-methylpropane-1,1-diyl)dicarbamate
• 英文别名: tert-butyl N-[(1S)-2-methyl-1-[4-[2-[(1S)-2-methyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]quinazolin-4-yl]quinazolin-2-yl]propyl]carbamate
• CAS: 1312716-51-0
• 化学式: C₃₄H₄₄N₆O₄
• 分子量: 600.761
• InChiKey: INUGPUYMGCYXSZ-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,1'S)-1,1'-(4,4'-biquinazoline-2,2'-diyl)bis(2-methylpropane-1,1-diyl)dicarbamate 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以93%的产率得到(1S,1'S)-1,1'-(4,4'-biquinazoline-2,2'-diyl)bis(2-methylpropan-1-amine)
  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：

  (R)-(R)-2-((tert-butoxycarbonyl)amino)-3-methylbutanoic (ethyl carbonic) anhydride 在 nickel(II) chloride hexahydrate 、 四丁基碘化铵 、 三苯基膦 、 N,N-二乙基苯胺 、 sodium hydroxide 、 锌 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 苯 为溶剂， 反应 13.08h， 生成 (S)-tert-butyl 2-methyl-1-(quinazolin-2-yl)propylcarbamate 、 tert-butyl (1S,1'S)-1,1'-(4,4'-biquinazoline-2,2'-diyl)bis(2-methylpropane-1,1-diyl)dicarbamate
  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

• Synthesis and asymmetric catalytic activity of (1S,1′S)-4,4′-biquinazoline-based primary amines
  作者：Murat Cakici、Mustafa Catir、Semistan Karabuga、Sabri Ulukanli、Hamdullah Kilic

  DOI：10.1016/j.tetasy.2011.01.009

  日期：2011.2

  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.