(1S)-1-methyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione | 437768-88-2

• 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: (1S)-1-methyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
• 英文别名: (1S)-1-methyl-2H-pyrazino[2,1-b]quinazoline-3,6-(1H,4H)-dione；2H-Pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione, 1-methyl-, (1S)-
• CAS: 437768-88-2
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: PITDHCRPZQTUPG-ZETCQYMHSA-N

物化性质

• 熔点：
  238-240 °C
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-1-methyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione 在 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 24.5h， 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
• 作为产物：
  描述：

  ethyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanyl-2-aminobenzoylglycinate 在 哌啶 、 溴 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成 (1S)-1-methyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
  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

• Total synthesis of asperlicin C, circumdatin F, demethylbenzomalvin A, demethoxycircumdatin H, sclerotigenin, and other fused quinazolinones
  作者：Ming-Chung Tseng、Huei-Yun Yang、Yen-Ho Chu

  DOI：10.1039/b910545j

  日期：——

  Using scandium triflate and microwaves, the direct double dehydrocyclization of anthranilate-containing tripeptides was achieved, affording the total syntheses of (i) quinazolino[3,2-a]benzodiazepinediones (1a–f), (ii) diazepino[2,1-b]quinazolinediones (2a–e), and (iii) pyrazino[2,1-b]quinazolinediones (3a–e) with good overall isolated yields (23–43%, 37–47% and 31–56%, respectively). Among the quinazolino[3,2-a]benzodiazepinediones synthesized, 1a (sclerotigenin), 1b (circumdatin F), and 1f (asperlicin C) are natural products.

  使用氟化铈和微波，成功实现了含有氨基苯甲酸的三肽的直接双脱氢环化，获得了以下化合物的整体合成：（i）喹唑啉[3,2-a]苯二氮杂杂环二酮（1a-f），（ii）二氮杂氟[2,1-b]喹唑啉二酮（2a-e），以及（iii）吡嗪[2,1-b]喹唑啉二酮（3a-e），它们的整体分离产率分别为23-43%，37-47%和31-56%。在合成的喹唑啉[3,2-a]苯二氮杂杂环二酮中，1a（紫锈碱）、1b（环夭碱F）和1f（曲霉素C）是天然产物。
• 10.1039/d4ob00529e
  作者：Zhang, Yuanmu、Zhu, Lingxuan、Lu, Yi、Lei, Xinsheng、Li, Yingxia

  DOI：10.1039/d4ob00529e

  日期：——

  skeletons occupy a prominent position in drug discovery. Even with currently available methods there still remain unmet needs for flexible access to such structures. Herein, we have explored a mild “one pot” procedure for the construction of various quinazolinone-[2,3]-fused polycycles. The procedure involves Pd-catalyzed carbonylation of N-(2-iodophenyl)acetamides, release of the masked terminal amine

  多种喹唑啉酮-[2,3]-稠合多环骨架在药物发现中占据着重要地位。即使采用当前可用的方法，对于灵活访问此类结构的需求仍然未得到满足。在此，我们探索了一种温和的“一锅法”程序来构建各种喹唑啉酮-[2,3]-稠合多环。该过程包括 Pd 催化的N- (2-碘苯基)乙酰胺的羰基化、掩蔽末端胺的释放以及两个连续的自发环化。这种普遍适用的方法具有从容易获得的起始材料中轻松组装前体、反应条件温和、操作不繁琐和多环多样性的特点。
• 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.
• 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.
• Three-Component One-Pot Total Syntheses of Glyantrypine, Fumiquinazoline F, and Fiscalin B Promoted by Microwave Irradiation
  作者：Ji-Feng Liu、Ping Ye、Bailin Zhang、Grace Bi、Katie Sargent、Libing Yu、Daniel Yohannes、Carmen M. Baldino

  DOI：10.1021/jo0508043

  日期：2005.8.1

  A microwave-promoted three-component one-pot reaction has been developed to provide access to the core pyrazino[2,1-b]quinazoline-3,6-dione (1) scaffold, which is common to several families of alkaloids with significant biological activities. By adapting this synthetic strategy through the use of selected Boc-amino acids and amino acid esters, we have accomplished highly efficient and concise total syntheses of glyantrypine (2), fumiquinazoline F (3), and fiscalin B (5), achieving overall yields of 55, 39, and 20%, respectively.