(+/-)-alantrypinone | 212911-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: (+/-)-alantrypinone
• 英文别名: Alantrypinone；(1'R,3R,12'R)-12'-methylspiro[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
• CAS: 212911-06-3
• 化学式: C₂₁H₁₆N₄O₃
• 分子量: 372.383
• InChiKey: COXWNIZQNAMTQL-NQERJWCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  90.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-alantrypinone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氘代二甲亚砜 为溶剂， 反应 2.5h， 生成 (+/-)-17-epi-alantrypinone
  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：

  (+/-)-17-epi-alantrypinone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氘代二甲亚砜 为溶剂， 反应 2.5h， 生成 (+/-)-alantrypinone
  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

文献信息

• A Concise Total Synthesis of (±)-Alantrypinone by a Novel Hetero-Diels−Alder Reaction
  作者：Andrew S. Kende、Junfa Fan、Zecheng Chen

  DOI：10.1021/ol030070l

  日期：2003.9.1

  [reaction: see text] An efficient total synthesis of (+/-)-alantrypinone (1) and its 17-epi isomer (17) has been accomplished employing a novel aza-Diels-Alder reaction as the key step. The reaction sequence comprises 8 steps starting from anthranilic acid and proceeds in 13.5% overall yield. An interesting anionic equilibration between 1 and its epimer 17 has also been discovered.

  [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。
• 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.