(S)-tert-butyl 1-(4-chloroquinazolin-2-yl)-2-methylpropylcarbamate | 1312716-47-4

• 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-methylpropylcarbamate
• 英文别名: tert-butyl N-[(1S)-1-(4-chloroquinazolin-2-yl)-2-methylpropyl]carbamate
• CAS: 1312716-47-4
• 化学式: C₁₇H₂₂ClN₃O₂
• 分子量: 335.834
• InChiKey: CJPPUWLPFXUQGG-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 1-(4-chloroquinazolin-2-yl)-2-methylpropylcarbamate 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-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 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 1.08h， 生成 (S)-tert-butyl 1-(4-chloroquinazolin-2-yl)-2-methylpropylcarbamate
  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

• Asymmetric transfer hydrogenation of ketones by N,N-containing quinazoline-based ruthenium(II) complexes
  作者：Cigdem Kucukturkmen、Ahmet Agac、Aysel Eren、Idris Karakaya、Mehmet Aslantas、Omer Celik、Sabri Ulukanli、Semistan Karabuga

  DOI：10.1016/j.catcom.2015.11.013

  日期：2016.1

  Coordination with RuCl2(PPh3)dppb gave ruthenium(II) N-heterocyclic complexes 4b–d. The structure of complex 4b was fully illuminated by X-ray crystallography. The steric environment of these chiral ruthenium complexes 4b–d was evaluated in asymmetric transfer hydrogenation (ATH) of prochiral ketones in the presence of NaOiPr by using 2-propanol as the hydrogen source and solvent. The resultant catalytic

  从光学纯的氨基酸开始合成了一组新的基于喹唑啉的手性配体。与RuCl 2（PPh 3）dppb配位得到钌（II）N-杂环配合物4b–d。配合物4b的结构通过X射线晶体学被完全照亮。通过使用2-丙醇作为氢源和溶剂，在NaO i Pr存在的情况下，在手性酮的不对称转移氢化（ATH）中评估了这些手性钌配合物4b-d的空间环境。所得的催化体系可以实现非常好的对映选择性（高达91％）和高产率（高达99％）。
• Design, synthesis and antitumor activity of 2-substituted quinazoline-4-amine derivatives
  作者：Menghan Wang、Jia Yu、Xinyi Huang、Gang Yu、Qi Liang、Sha Cheng、Xueling Meng、Guangcan Xu、Huimin Li、Heng Luo、Bixue Xu

  DOI：10.1016/j.bmc.2024.117660

  日期：2024.3

  The structures of the thirty-two newly synthesized compounds were confirmed by H NMR, C NMR and ESI-MS. The anticancer activity against chronic myeloid leukemia cells (K562), non-small cell lung cancer cells (A549), human prostate cancer cells (PC3), and cervical cancer cells (HeLa) of the target compounds was evaluated. Among them, the inhibition ratio of compounds , , , and against four cancer cells

  Werner (WRN) 综合征蛋白是一种多功能酶，具有解旋酶、ATP 酶和核酸外切酶活性，这些活性对于人类细胞中许多 DNA 相关的活动是必需的。最近的研究确定 WRN 是癌症的合成致死靶点。本研究在喹唑啉结构优化的基础上，设计合成了一系列新型-芳基喹唑啉-4-胺类似物。 32个新合成的化合物的结构经H NMR、C NMR和ESI-MS确认。评价了目标化合物对慢性粒细胞白血病细胞（K562）、非小细胞肺癌细胞（A549）、人前列腺癌细胞（PC3）和宫颈癌细胞（HeLa）的抗癌活性。其中化合物 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 等化合物在5μM浓度下对四种癌细胞的抑制率均超过50%。化合物和化合物在K562细胞中的IC50值分别为0.3±0.01μM和0.05±0.02μM，与HeLa和A549细胞相比，对K562细胞更敏感。此
• 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.