5,5a,6,7,8,9-hexahydro-11H-pyrido<2,1-b>quinazoline | 5516-83-6

• 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: 5,5a,6,7,8,9-hexahydro-11H-pyrido<2,1-b>quinazoline
• 英文别名: 5a,6,7,8,9,11-hexahydro-5H-pyrido[2,1-b]quinazoline；5,5a,6,7,8,9-Hexahydro-11H-pyrido<2,1-b>chinazolin；5,6,7,8,9,11-Hexahydro-pyrido<2,1-b>chinazolin；5,6,7,8,9,11-hexahydro-5aH-pyrido[2,1-b]quinazoline；5,6,7,8,9,11-Hexahydro-5aH-pyrido[2,1-b]chinazolin
• CAS: 5516-83-6
• 化学式: C₁₂H₁₆N₂
• 分子量: 188.272
• InChiKey: KBSZGTPLNRJRGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5a,6,7,8,9-hexahydro-11H-pyrido<2,1-b>quinazoline 在 叔丁基过氧化氢 、 potassium iodide 、 哌啶 作用下， 以 癸烷 、 乙醇 为溶剂， 反应 37.0h， 以59%的产率得到8,9-二氢-6H-吡啶并[2,1-b]喹唑啉-11(7h)-酮
  参考文献：
  名称：

  选择性乙酸铜(II)和碘化钾催化缩醛胺氧化为二氢喹唑啉和喹唑啉酮生物碱。

  摘要：

  乙酸铜(II)/乙酸/O2 和碘化钾/叔丁基过氧化氢体系分别影响稠环缩醛胺选择性氧化为二氢喹唑啉和喹唑啉酮。这些方法使得能够容易地制备多种喹唑啉生物碱天然产物及其类似物。

  DOI：

  10.3762/bjoc.9.135
• 作为产物：
  描述：

  8,9-二氢-6H-吡啶并[2,1-b]喹唑啉-11(7h)-酮 在 盐酸 、 乙醇 、 sodium 、 溶剂黄146 、 锌 作用下， 生成 5,5a,6,7,8,9-hexahydro-11H-pyrido<2,1-b>quinazoline
  参考文献：
  名称：

  Spaeth; Platzer, Chemische Berichte, 1935, vol. 68, p. 2221,2225

  摘要：

  DOI：

文献信息

• The Stereochemistry of Organometallic Compounds. XLII. The Preparation of [2,1-b]Quinazolines Involving Rhodium-Catalysed Hydroformylation of 2-Amino-N-Alkenylbenzylamines
  作者：EM Campi、J Habsuda、WR Jackson、CAM Jonasson、QJ Mccubbin

  DOI：10.1071/ch9952023

  日期：——

  Rhodium-catalysed reactions of 2-amino-N-alkenylbenzylamines with H2/CO give hexahydro-pyrrolo- and hexahydropyrido -[2,1-b] quinazolines. Reactions of N-allyl derivatives give a single regioisomer, and reactions of but-3-enyl analogues give mixtures of pyrrolo and pyrido derivatives. Some reactions give significant amounts (10-30%) of tetrahydro derivatives. The origin of these compounds remains unclear.

  铑催化 2-氨基-N-烯基苄胺与 H2/CO 的反应生成六氢吡咯并六氢吡啶并[2,1-b]喹唑啉。与 N-烯丙基衍生物反应会产生单一的区域异构体，而与丁-3-烯基类似物反应则会产生吡咯和吡啶衍生物的混合物。有些反应会产生大量（10-30%）四氢衍生物。这些化合物的来源仍不清楚。
• Selective copper(II) acetate and potassium iodide catalyzed oxidation of aminals to dihydroquinazoline and quinazolinone alkaloids
  作者：Matthew T Richers、Chenfei Zhao、Daniel Seidel

  DOI：10.3762/bjoc.9.135

  日期：——

  acetate/acetic acid/O2 and potassium iodide/tert-butylhydroperoxide systems are shown to affect the selective oxidation of ring-fused aminals to dihydroquinazolines and quinazolinones, respectively. These methods enable the facile preparation of a number of quinazoline alkaloid natural products and their analogues.

  乙酸铜(II)/乙酸/O2 和碘化钾/叔丁基过氧化氢体系分别影响稠环缩醛胺选择性氧化为二氢喹唑啉和喹唑啉酮。这些方法使得能够容易地制备多种喹唑啉生物碱天然产物及其类似物。
• Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with o-Aminobenzaldehydes: Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone, and Ruteacarpine
  作者：Daniel Seidel、Matthew Richers、Indubhusan Deb、Alena Platonova、Chen Zhang

  DOI：10.1055/s-0033-1338852

  日期：——

  Secondary amines undergo redox-neutral reactions with aminobenzaldehydes under conventional and microwave heating to furnish polycyclic aminals via amine alpha-amination/N-alkylation. This unique alpha-functionalization reaction proceeds without the involvement of transition metals or other additives. The resulting aminal products are precursors for various quinazolinone alkaloids and their analogues.
• Ring-fused aminals: catalyst and solvent-free microwave-assisted α-amination of nitrogen heterocycles
  作者：Vivek Polshettiwar、Rajender S. Varma

  DOI：10.1016/j.tetlet.2008.09.166

  日期：2008.12

  A high-yield synthesis of ring-fused aminals via microwave (MW)-assisted alpha-amination of nitrogen heterocycles at 130 degrees C under solvent- and catalyst-free conditions is described. (C) 2008 Elsevier Ltd. All rights reserved.
• Redox Condensations of <i>o</i>-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family
  作者：Oleg I. Afanasyev、Evgeniya Podyacheva、Alexander Rudenko、Alexey A. Tsygankov、Maria Makarova、Denis Chusov

  DOI：10.1021/acs.joc.0c00794

  日期：2020.7.17

  A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and

  已开发了由散装化学品对天然产物vasicinone系列进行的全合成。利用五羰基铁作为还原剂，将邻硝基苯甲醛与胺进行还原性缩合反应，随后进行氧化，可在温和的条件下形成多种多环含氮杂环。对映体纯的vasicinone，rutaecarpine，isaindigotone和luotonin是由易得的起始原料（如羟脯氨酸，硝基苯甲醛，吡咯烷和哌啶）在两到四个操作步骤中合成的，无需色谱分离。测试了所有产品的抗真菌活性。