(+)-(1S)-3-ethoxy-1-methyl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one | 606977-77-9

• 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)-3-ethoxy-1-methyl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one
• 英文别名: 3-ethoxy-1-methyl-1,4-dihydro-2,4a,9-triaza-anthracen-10-one；(1S)-3-ethoxy-1-methyl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one
• CAS: 606977-77-9
• 化学式: C₁₄H₁₅N₃O₂
• 分子量: 257.292
• InChiKey: VUIYTCFZYRQNQL-VIFPVBQESA-N

物化性质

• 沸点：
  415.5±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.48
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+)-(1S)-3-ethoxy-1-methyl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 氯仿 、 苯 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  Total Synthesis of (±)-Alantrypinone by Hetero Diels−Alder Reaction

  摘要：

  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.

  DOI：

  10.1021/jo030273n
• 作为产物：
  描述：

  西维来司他杂质1 在 哌啶 、 溴 、 sodium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 32.25h， 生成 (+)-(1S)-3-ethoxy-1-methyl-1,4-dihydropyrazino[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

• 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.
• A new stereocontrolled approach to fused polycyclic compounds containing a diketopiperazine ring
  作者：Fernando Hernández、Carmen Avendaño、Mónica Söllhuber

  DOI：10.1016/j.tetasy.2005.08.034

  日期：2005.10

  Representative (1S)- and (4S)-alkyl-1,4-dihydropyrazino[2,1-b]quinazoline-3,6-dione lactim ethers were regio- and diastereoselectively alkylated after metallation to give the corresponding 1,4-trans-isomers with retention of the stereocentres. The results were compared with the previously studied lactams. The (1R,4S)-dialkyl derivatives obtained by C(1)-alkyation with bifunctional reagents were lately cyclized to complex polycyclic compounds through a second N(2)-alkylation promoted by sodium iodide. (c) 2005 Elsevier Ltd. All rights reserved.