3-Prop-2-enylimidazol-4-amine | 1314930-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Prop-2-enylimidazol-4-amine
• CAS: 1314930-75-0
• 化学式: C₆H₉N₃
• 分子量: 123.158
• InChiKey: DGOLARQRXMMCPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Prop-2-enylimidazol-4-amine 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.33h， 生成 3-propyl-3H-imidazo[4,5-b]pyridin-6-amine
  参考文献：
  名称：

  Design, synthesis and transformation of some heteroannulated 3-aminopyridines—purine isosteres with exocyclic nitrogen atom

  摘要：

  The synthesis of 1-deazapurines and isosteres bearing the exocyclic nitrogen atom at position-1 was developed basing on the formal [3+3]-cyclization reaction of nitro-malonaldehyde with the set of electron-excessive aminoheterocycles. Through the functionalization of the purine-like scaffolds synthesized the diversity of compounds furnished in the possition-1 with aryl, alkinyl, and vinyl rests, were obtained. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.026
• 作为产物：
  描述：

  N-(cyanomethyl)-N'-prop-2-enylmethanimidamide 以 二氯甲烷 为溶剂， 生成 3-Prop-2-enylimidazol-4-amine
  参考文献：
  名称：

  通过 1-取代的 1H-Imidazol-5-胺与 3-Nitro-4H-chromen-4-one 的环缩合反应有效合成 6-Nitro-和 6-Amino-3H-imidazo[4,5-b]pyridines

  摘要：

  3-nitro-4 H-chromen-4-one与原位反应生成1-取代的5-amino-1 H-imidazoles提供了一组1-取代的6-nitro-3 H-imidazo[4,5-B]代表潜在的腺苷脱氨酶 (ADA) 抑制剂的吡啶。硝基的还原导致相应的 6-amino-3 H-imidazo[4,5-B] 吡啶的形成。

  DOI：

  10.1055/s-0030-1258538

文献信息

• 3-Methoxalylchromone - A Versatile Reagent for the Regioselective Synthesis of 1-Desazapurine
  作者：Viktor Iaroshenko、Peter Langer、Dmytro Ostrovskyi、Iftikhar Ali、Satenik Mkrtchyan、Alexander Villinger、Andrei Tolmachev

  DOI：10.1055/s-0030-1258339

  日期：2011.1

  The reaction of 5-amino-1H-imidazoles with 3-methoxalylchromone provided a set of imidazo[4,5-b]pyridines (1-des­azapurines) bearing the CO2Me substituent at the α-position of the pyridine core. The corresponding acids were synthesized by subsequent hydrolysis of the ester function. Being typical purine isos­teres, 1-desazapurines are considered to be potent pharmacophores, and are widely used in drug design and medicinal chemistry.

  5-amino-1H-imidazoles 与 3-methoxalylchromone 的反应产生了一组咪唑并[4,5-b]吡啶（1-desazapurines），其吡啶核心的 δ 位带有 CO2Me 取代基。随后通过水解酯功能合成了相应的酸。作为典型的嘌呤异构体，1-desazapurines 被认为是强效药亲和剂，广泛应用于药物设计和药物化学。
• [DE] HETEROBICYCLISCHE VERBINDUNGEN ALS FUNGIZIDE<br/>[EN] HETEROBICYCLIC COMPOUNDS USED AS FUNGICIDES<br/>[FR] COMPOSES HETEROCYCLIQUES UTILISES EN TANT QUE FONGICIDES
  申请人：BASF AG

  公开号：WO2004092175A1

  公开（公告）日：2004-10-28

  Die Erfindung betrifft bicyclische Verbindungen der allgemeinen Formel (I) sowie die landwirtschaftlich verträglichen Salze von Verbindungen (I), Pflanzenschutzmittel, enthaltend wenigstens eine Verbindung der allgemeinen Formel (I) und/oder landwirtschaftlich verträgliches Salz von (I) und wenigstens einen flüssigen oder festen Trägerstoff sowie ein Verfahren zur Bekämpfung von pflanzenpathogenen Schadpilzen.

  这项发明涉及一般式(I)的双环连接物，以及连接物(I)的农业可容忍盐、包含至少一种一般式(I)连接物和/或(I)的农业可容忍盐、至少一种液体或固体载体的植物保护剂，以及一种用于对抗植物病原真菌的方法。
• Heterobicyclic compounds used as fungicides
  申请人：i Blasco Tormo Jordi

  公开号：US20060199801A1

  公开（公告）日：2006-09-07

  Bicyclic compounds of the formula I in which A 1 or A 5 is C and the other of the two variables A 1 , A 5 is N, C or C—R 3 ; A 2 , A 3 , A 4 independently of one another are N or C—R 3a , where one of the variables A 2 , A 3 or A 4 may also be S or a group N—R 4 if A 1 and A 5 are both C, and where A 4 is not N or C—R 3a if A 1 is N, A 3 is C—R 3a and A 5 is C, and where A 1 is attached to A 2 and A 3 to A 4 or A 2 is attached to A 3 and A 4 to A 5 or A 1 is attached to A 5 and A 2 to A 3 or A 1 is attached to A 5 and A 3 to A 4 or A 1 is attached to A 2 and A 4 to A 5 by double bonds; n is 0, 1, 2, 3, 4 or 5; R a is halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy or C(O)R 5 ; R 1 is halogen, cyano, C 1 -C 10 -alkyl, where a carbon atom of the C 1 -C 10 -alkyl radical may be replaced by a silicium atom, C 1 -C 6 -haloalkyl, C 2 -C 10 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, where the cycloalkyl moiety of the two last-mentioned groups may be unsubstituted or contain 1, 2, 3, 4, 5, or 6 radicals selected from the group consisting of C 1 -C 4 -alkylidene, C 1 -C 4 -alkyl, halogen, C 1 -C 4 -haloalkyl and hydroxy and the alkyl moiety of C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl may be unsubstituted or contain 1, 2, 3, or 4 radicals selected from the group consisting of halogen, C 1 -C 4 -haloalkyl and hydroxy, C 5 -C 8 -cycloalkenyl which may be unsubstituted or contain 1, 2, 3 or 4 radicals selected from the group consisting of C 1 -C 4 -alkyl, halogen, C 1 -C 4 -haloalkyl and hydroxy, OR 6 , SR 6 , NR 7 R 8 , a radical of the formula —C(R 11 )(R 12 )C(═NOR 13 )(R 14 ) or a radical of the formula —C(═NOR 15 )C(═NOR 16 )(R 17 ); R 2 is halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 5 -C 8 -cycloalkenyl, OR 6 , SR 6 or NR 7 R 8 ; and the agriculturally acceptable salts of the compounds I, crop protection compositions comprising at least one compound of the formula I and/or an agriculturally acceptable salt of I and at least one solid or liquid carrier and a method for controlling phytopathogenic harmful fungi are described.

  化合物I的双环化合物，其中A1或A5为C，而另一个变量A1、A5为N、C或C—R3；A2、A3、A4彼此独立且为N或C—R3a，其中变量A2、A3或A4中的一个也可以是S或一个N—R4基团，如果A1和A5都是C，则A4不是N或C—R3a，如果A1是N，A3是C—R3a，A5是C，则A1附着于A2，A3附着于A4；或A2附着于A3，A4附着于A5；或A1附着于A5，A2附着于A3；或A1附着于A5，A3附着于A4；或A1附着于A2，A4附着于A5，其中双键连接；n为0、1、2、3、4或5；Ra为卤素、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C2-C6烯基、C2-C6烯氧基或C(O)R5；R1为卤素、氰基、C1-C10烷基（其中C1-C10烷基基团的一个碳原子可以被硅原子替换）、C1-C6卤代烷基、C2-C10烯基、C2-C6卤代烯基、C2-C6炔基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基（其中最后两个基团的环烷基部分可以是未取代的或包含1、2、3、4、5或6个从C1-C4烷基亚基、卤素、C1-C4卤代烷基和羟基中选择的基团，而C3-C8环烷基-C1-C4烷基的烷基部分可以是未取代的或包含1、2、3或4个从卤素、C1-C4卤代烷基和羟基中选择的基团）、C5-C8环烯基（可以是未取代的或包含1、2、3或4个从C1-C4烷基、卤素、C1-C4卤代烷基和羟基中选择的基团）、OR6、SR6、NR7R8、式—C(R11)(R12)C(═NOR13)(R14)的基团或式—C(═NOR15)C(═NOR16)(R17)的基团；R2为卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C3-C8环烷基、C5-C8环烯基、OR6、SR6或NR7R8；以及化合物I的农业可接受盐，包含至少一种化合物I和/或化合物I的农业可接受盐以及至少一种固体或液体载体的作物保护组合物和控制植物病原真菌的方法。
• HETEROBICYCLISCHE VERBINDUNGEN ALS FUNGIZIDE
  申请人：BASF Aktiengesellschaft

  公开号：EP1620436A1

  公开（公告）日：2006-02-01
• Design, synthesis and transformation of some heteroannulated 3-aminopyridines—purine isosteres with exocyclic nitrogen atom
  作者：Viktor O. Iaroshenko、Marcelo Vilches-Herrera、Ashot Gevorgyan、Satenik Mkrtchyan、Knar Arakelyan、Dmytro Ostrovskyi、Muhammad S.A. Abbasi、Linda Supe、Ani Hakobyan、Alexander Villinger、Dmitriy M. Volochnyuk、Andrei Tolmachev

  DOI：10.1016/j.tet.2012.11.026

  日期：2013.1

  The synthesis of 1-deazapurines and isosteres bearing the exocyclic nitrogen atom at position-1 was developed basing on the formal [3+3]-cyclization reaction of nitro-malonaldehyde with the set of electron-excessive aminoheterocycles. Through the functionalization of the purine-like scaffolds synthesized the diversity of compounds furnished in the possition-1 with aryl, alkinyl, and vinyl rests, were obtained. (C) 2012 Elsevier Ltd. All rights reserved.