(S)-tert-butyl 1-(4-chloroquinazolin-2-yl)-2-phenylethylcarbamate | 1312716-49-6

• 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-chloroquinazolin-2-yl)-2-phenylethylcarbamate
• 英文别名: t-butyl (S)-(1-(4-chloroquinazolin-2-yl)-2-phenylethyl)carbamate
• CAS: 1312716-49-6
• 化学式: C₂₁H₂₂ClN₃O₂
• 分子量: 383.878
• InChiKey: WTTJFHQWOVQYBC-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 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：
  64.11
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 1-(4-chloroquinazolin-2-yl)-2-phenylethylcarbamate 在 nickel(II) chloride hexahydrate 、 四丁基碘化铵 、 三苯基膦 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (1S,1'S)-1,1'-(4,4'-biquinazoline-2,2'-diyl)bis(2-phenylethanamine)
  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：

  L-苯丙氨酸 在 sodium carbonate 、 三乙胺 、 N,N-二乙基苯胺 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 水 、 苯 为溶剂， 反应 13.75h， 生成 (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

文献信息

• Synthesis of aminomethyl quinazoline based ruthenium (II) complex and its application in asymmetric transfer hydrogenation under mild conditions
  作者：Ahmet Agac、Idris Karakaya、Irfan Sahin、Sedat Emir、Semistan Karabuga、Sabri Ulukanli

  DOI：10.1016/j.jorganchem.2016.07.001

  日期：2016.9

  The new chiral aminomethyl quinazoline (amq) type ligand derived from l-phenylalanine was synthesized and coordinated with [RuCl2(PPh3)dppb] to obtain ruthenium(II) complex. This catalyst displayed considerable reactivity (up to 97% ee and 99% conversion) in the asymmetric transfer hydrogenation of ketones using 2-propanol as a hydrogen source in the presence of NaOiPr.

  合成了一种新的由1-苯基丙氨酸衍生的手性氨基甲基喹唑啉（amq）型配体，并与[RuCl 2（PPh 3）dppb]配位得到钌（II）配合物。在NaO i Pr存在的情况下，使用2-丙醇作为氢源，在酮的不对称转移加氢中，该催化剂表现出可观的反应性（高达97％ee和99％的转化率）。