(S)-tert-butyl 1-(4-oxo-3-p-tolyl-3,4-dihydroquinazolin-2-yl)ethylcarbamate

• 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-p-tolyl-3,4-dihydroquinazolin-2-yl)ethylcarbamate
• 英文别名: tert-butyl (S)-(1-(4-oxo-3-(p-tolyl)-3,4-dihydroquinazolin-2-yl)ethyl)carbamate；tert-butyl N-[(1S)-1-[3-(4-methylphenyl)-4-oxoquinazolin-2-yl]ethyl]carbamate
• 化学式: C₂₂H₂₅N₃O₃
• 分子量: 379.459
• InChiKey: XVSKVJDKYJEZQD-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-N-对甲苯苯甲酰胺 在 碘 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (S)-tert-butyl 1-(4-oxo-3-p-tolyl-3,4-dihydroquinazolin-2-yl)ethylcarbamate
  参考文献：
  名称：

  Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones

  摘要：

  A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I-2 for the intramolecular dehydrative cyclization of diamides. The protecting groups -Boc, -Fmoc and -Cbz tolerated the present reaction conditions and we did not observe any racemization. The present protocol has also been used as a key step for the efficient four-step syntheses of the naturally occurring quinazolinones, sclerotigenin, (-)-circumdatin-F and (-)-fumiquinazoline-F. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.032

文献信息

• Construction of <i>N</i> ‐Boc‐2‐Alkylaminoquinazolin‐4(3 <i>H</i> )‐Ones via a Three‐Component, One‐Pot Protocol Mediated by Copper(II) Chloride that Spares Enantiomeric Purity
  作者：Xiaoyu Li、Jennifer E. Golden

  DOI：10.1002/adsc.202001279

  日期：2021.3.16

  2‐alkylquinazolinones are key synthetic intermediates, but their preparation in high optical purity is challenging. Thus, a multicomponent procedure integrating anthranilic acids, N‐Boc‐amino acids, and amines in the presence of methanesulfonyl chloride, N‐methylimidazole, and copper(II) chloride was developed to mildly afford N‐Boc‐2‐alkylaminoquinazolin‐4(3H)‐ones with excellent preservation of enantiomeric

  手性2-烷基喹唑啉酮是关键的合成中间体，但其高光学纯度的制备具有挑战性。因此，开发了一种在甲磺酰氯、 N-甲基咪唑和氯化铜(II)存在下整合邻氨基苯甲酸、 N -Boc-氨基酸和胺的多组分程序，以温和地提供N -Boc-2-烷基氨基喹唑啉-4( 3 H )-具有出色的对映体纯度保留 (>99% ee)。氯化铜(II)对于保持对映体纯度至关重要，并且反应组分结构变化具有良好的耐受性，从而形成一种高效的一体化程序，促进连续偶联、内酯化、氨解和环化，并获得良好的收率。该方法适用于快速组装用于合成高浓度喹唑啉酮类药物的四种关键中间体，包括几种 PI3K 抑制剂药物。
• Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones
  作者：Umesh A. Kshirsagar、Santosh B. Mhaske、Narshinha P. Argade

  DOI：10.1016/j.tetlet.2007.03.032

  日期：2007.4

  A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I-2 for the intramolecular dehydrative cyclization of diamides. The protecting groups -Boc, -Fmoc and -Cbz tolerated the present reaction conditions and we did not observe any racemization. The present protocol has also been used as a key step for the efficient four-step syntheses of the naturally occurring quinazolinones, sclerotigenin, (-)-circumdatin-F and (-)-fumiquinazoline-F. (c) 2007 Elsevier Ltd. All rights reserved.