(1S)-3-ethoxy-1-propan-2-yl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one | 943253-33-6

• 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: (1S)-3-ethoxy-1-propan-2-yl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one
• CAS: 943253-33-6
• 化学式: C₁₆H₁₉N₃O₂
• 分子量: 285.346
• InChiKey: HXYMBFXMCCDTOL-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (1S)-3-ethoxy-1-propan-2-yl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 Eu(fod)3 作用下， 以 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 16.5h， 生成 (1'R,3S,12'R)-12'-propan-2-ylspiro[1H-indole-3,16'-2,10,13-triazatetracyclo[10.2.2.02,11.04,9]hexadeca-4,6,8,10-tetraene]-2,3',14'-trione
  参考文献：
  名称：

  Acid-Catalyzed Aza-Diels−Alder Reactions for the Total Synthesis of (±)-Lapatin B

  摘要：

  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.

  DOI：

  10.1021/jo0705162
• 作为产物：
  描述：

  N-Boc-L-缬氨酸 在 吡啶 、 亚磷酸三苯酯 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 40.17h， 生成 (1S)-3-ethoxy-1-propan-2-yl-1,4-dihydropyrazino[2,1-b]quinazolin-6-one
  参考文献：
  名称：

  Acid-Catalyzed Aza-Diels−Alder Reactions for the Total Synthesis of (±)-Lapatin B

  摘要：

  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.

  DOI：

  10.1021/jo0705162

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.