3-Ethoxy-1-methylpyrazino[2,1-b]quinazolin-6-one | 606977-75-7

• 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: 3-Ethoxy-1-methylpyrazino[2,1-b]quinazolin-6-one
• CAS: 606977-75-7
• 化学式: C₁₄H₁₃N₃O₂
• 分子量: 255.276
• InChiKey: RICFADYXHUYNNB-UHFFFAOYSA-N

物化性质

• 沸点：
  430.5±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Ethoxy-1-methylpyrazino[2,1-b]quinazolin-6-one 在 盐酸 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 27.0h， 生成 (+/-)-17-epi-alantrypinone
  参考文献：
  名称：

  通过新的杂Diels-Alder反应进行简明的全合成（+/-）-丙三烯酮。

  摘要：

  [反应：见正文]利用新型的aza-Diels-Alder反应作为关键步骤，完成了（+/-）-丙二烯酮（1）及其17-表异构体（17）的有效全合成。反应顺序包括从邻氨基苯甲酸开始的8个步骤，总产率为13.5％。还发现了1与其差向异构体17之间有趣的阴离子平衡。

  DOI：

  10.1021/ol030070l
• 作为产物：
  描述：

  ethyl-N-{2-[(S)-1-N-[(9H-fluoren-9-ylmethoxy)carbonyl]aminoethyl]-4H-3,1-benzoxazin-4-ylidene}glycinate 在 哌啶 、 sodium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 27.5h， 生成 3-Ethoxy-1-methylpyrazino[2,1-b]quinazolin-6-one
  参考文献：
  名称：

  通过新的杂Diels-Alder反应进行简明的全合成（+/-）-丙三烯酮。

  摘要：

  [反应：见正文]利用新型的aza-Diels-Alder反应作为关键步骤，完成了（+/-）-丙二烯酮（1）及其17-表异构体（17）的有效全合成。反应顺序包括从邻氨基苯甲酸开始的8个步骤，总产率为13.5％。还发现了1与其差向异构体17之间有趣的阴离子平衡。

  DOI：

  10.1021/ol030070l

文献信息

• Control of Hetero-Diels-Alder Stereoselectivity through Solvent Polarity and Brønsted or Lewis Acid Catalysis; Theory and Experiment
  作者：Olivier Loiseleur、Kendall Houk、Jérôme Cassayre、Dominique Leca、Francesca Gaggini、Susan Pieniazek、Jennifer Luft

  DOI：10.1055/s-0033-1340046

  日期：——

  The stereoselectivity of cycloadditions involving 3-methyleneoxindole and 2-azadienes can be controlled by solvent polarity and by Lewis or Bronsted acid catalysis. The improvements in selectivity are advantageous for the synthesis of spiroquinazoline alkaloids such as alantrypinone and lapatin B.

  涉及 3-亚甲基羟吲哚和 2-氮杂二烯的环加成的立体选择性可以通过溶剂极性和路易斯或布朗斯台德酸催化来控制。选择性的提高有利于合成螺喹唑啉生物碱，如阿兰曲酮和拉帕汀 B。
• Asymmetric Palladium‐Catalyzed Dearomative Intramolecular <i>N</i>‐Alkylation Reaction: Enantioselective Total Synthesis of (−)‐Spiroquinazoline
  作者：Rongxing Zhang、Zhijie Wu、Shaoqian Yang、Dawei Ma

  DOI：10.1002/adsc.202300372

  日期：2023.6.20

  Tricyclic imidazo[1,2-a]-indol-3-ones have been found in several classes of alkaloids. We report here an asymmetric approach to instal substituted imidazo[1,2-a]-indol-3-ones, which relied on a Pd/diamidophosphite-catalyzed intramolecular dearomative allylic substitution of 1,3-disubstituted indoles derived from 3-formylindoles and amino acids. Enantioselective total syntheses of (−)-spiroquinazoline

  在几类生物碱中发现了三环咪唑并[1,2-a]-吲哚-3-酮。我们在此报告了一种安装取代的咪唑并[1,2-a]-吲哚-3-酮的不对称方法，该方法依赖于钯/二酰氨基亚磷酸酯催化的分子内脱芳香烯丙基取代源自3-甲酰基吲哚的1,3-二取代吲哚和氨基酸。实现了(−)-螺喹唑啉和三种相关生物碱的对映选择性全合成。
• Alantrypinone and its derivatives: Synthesis and antagonist activity toward insect GABA receptors
  作者：Takayuki Watanabe、Mitsuhiro Arisawa、Kenji Narusuye、Mohommad Sayed Alam、Kazumi Yamamoto、Masaaki Mitomi、Yoshihisa Ozoe、Atsushi Nishida

  DOI：10.1016/j.bmc.2008.11.017

  日期：2009.1

  The gamma-aminobutyric acid (GABA) receptor bears important sites of action for insecticides. Alantrypinone is an insecticidal alkaloid that acts as a selective antagonist for housefly (vs rat) GABA receptors, and is considered to be a lead compound for the development of a safer insecticide. In an attempt to obtain compounds with greater activity, a series of racemic alantrypinone derivatives were systematically synthesized using hetero Diels-Alder reactions, and a total of34 compounds were examined for their ability to inhibit the specific binding of [H-3]4'-ethynyl-4-n-propylbicycloorthobenzoate, a high-affinity non-competitive antagonist, to housefly-head membranes. The assay results showed that (1) there is no significant difference between the potencies of natural (+)-alantrypinone and its synthetic racemate; (2) the amide NHs at the 2- and 18-positions are important for high activity; (3) there is a considerable drop in potency for compounds without an aromatic ring at the 16-position; and (4) a large substituent at the 3-position is detrimental to high activity. (c) 2008 Elsevier Ltd. All rights reserved.
• Acid-Catalyzed Aza-Diels−Alder Reactions for the Total Synthesis of (±)-Lapatin B
  作者：Dominique Leca、Francesca Gaggini、Jérôme Cassayre、Olivier Loiseleur、Susan N. Pieniazek、Jennifer A. R. Luft、K. N. Houk

  DOI：10.1021/jo0705162

  日期：2007.5.1

  A 5-step total synthesis of microfungal alkaloid (+/-)-lapatin B has been accomplished via a key 2-aza-Diels-Alder reaction. Bronsted acids catalyze the cycloaddition step and provide improved exo selectivity. This synthetic route has been applied to the construction of related spiro-quinazoline structures.
• Total Synthesis of (±)-Alantrypinone by Hetero Diels−Alder Reaction
  作者：Zecheng Chen、Junfa Fan、Andrew S. Kende

  DOI：10.1021/jo030273n

  日期：2004.1.1

  An efficient total synthesis of (+/-)-alantrypinone 4 by hetero Diels-Alder reaction of a novel pyrazine diene 9 with either a functionalized 3-alkylideneoxindole or 3-methyleneoxindole itself is described. The Diels-Alder reactions provide both the desired regiochemistry and exo selectivity. An interesting anionic equilibration between alantrypinone 4 and its epimer 31 or between its ester analogues 23 and 24 has been demonstrated, and a mechanism has been proposed.