1-azabicyclo<2.2.2>octane-3-spiro-2'-dioxolane | 26814-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 1-azabicyclo<2.2.2>octane-3-spiro-2'-dioxolane
• 英文别名: β-Oxoquinuclidine-ethylenketal；2-(3-Chinuclidinyl)-1,3-dioxolan；3-Chinuclidinon Ethylenketal；spiro[1-aza-bicyclo[2.2.2]octane-3,2'-[1,3]dioxolane]；3-Quinuclidinone ethyleneketal；spiro[1,3-dioxolane-2,3'-1-azabicyclo[2.2.2]octane]
• CAS: 26814-49-3
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: VHDXCNZKEDRQBW-UHFFFAOYSA-N

物化性质

• 沸点：
  248.7±25.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-azabicyclo<2.2.2>octane-3-spiro-2'-dioxolane 、 碘甲烷 以 丙酮 为溶剂， 以80%的产率得到1-azabicyclo<2.2.2>octane-3-spiro-2'-dioxolane methiodide
  参考文献：
  名称：

  Synthesis and selective activity of cholinergic agents with rigid skeletons. II.

  摘要：

  三种类型的化合物（喹宁环-3-螺-2'-二氧六环（A）、哌啶-4-螺-2'-二氧六环（B）和哌啶-4-螺-2'-(4'-氧二氧六环)（C））及其甲碘化物被合成。为了研究这些具有刚性骨架的化合物与已知毒蕈碱样作用剂之间活性的关系，对其胆碱能样活性进行了检验。

  DOI：

  10.1248/cpb.29.3019
• 作为产物：
  描述：

  3-奎宁环酮盐酸盐 以 sodium hydroxide 、 乙二醇 为溶剂， 生成 1-azabicyclo<2.2.2>octane-3-spiro-2'-dioxolane
  参考文献：
  名称：

  Piperidine compounds as calcium channel blockers

  摘要：

  本发明揭示了以下式的化合物##STR1##及其任何对映体或任何混合物，或其药学上可接受的加盐物，其中X、Ar、R、R.sup.1、R.sup.2、n如本文所定义。

  公开号：

  US05981539A1
• 作为试剂：
  描述：

  苯基乙烯基砜 、 O6-TBS-D-α-methylalloside 在 1-azabicyclo<2.2.2>octane-3-spiro-2'-dioxolane 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 四丁基磷酸氢铵 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 以59%的产率得到C₂₁H₃₆O₈SSi
  参考文献：
  名称：

  通过有机光氧化还原催化肌醇的位点选择性 C-H 烷基化

  摘要：

  与芳族烯烃的位点选择性光氧化还原反应能够在 C4 上直接烷基化未保护的肌醇。这些反应的功效可以通过修改 HAT 试剂的结构来微调。这些反应开启了肌醇选择性 C-H 烷基化的可能性，而无需多步保护-去保护策略。

  DOI：

  10.1039/d2cc03569c

文献信息

• Methods for Preparing Azoxystrobin and Intermediate Thereof
  申请人：NUTRICHEM COMPANY LIMITED

  公开号：US20160200687A1

  公开（公告）日：2016-07-14

  The present invention discloses a method for preparing azoxystrobin intermediates represented by formulae (1) and (2), comprising: controlling a compound represented by formula (3) to contact with sodium methoxide and 4,6-dichloropyrimidine, to obtain a mixture of intermediates represented by formulae (1) and (2), in the existence of a catalyst, the catalyst is an azabicyclic compound or its salt. The present invention further discloses a method for preparing azoxystrobin, comprising: controlling the intermediate represented by formula (2) provided in the present invention to react with 2-cyanophenol or its salt under the catalytic action of an azabicyclic compound or its salt, to obtain an azoxystrobin compound represented by formula (4). The method provided in the present invention has advantages including high transformation ratio, high product purity, easy and convenient operation, and environmental friendliness.

  本发明揭示了一种制备由式（1）和（2）表示的阿托霉唑中间体的方法，包括：控制由式（3）表示的化合物与甲氧基钠和4,6-二氯嘧啶接触，以在存在催化剂的情况下获得由式（1）和（2）表示的中间体的混合物，其中催化剂为吡啶环化合物或其盐。本发明还揭示了一种制备阿托霉唑的方法，包括：控制本发明提供的由式（2）表示的中间体，在吡啶环化合物或其盐的催化作用下与2-氰基苯酚反应，以获得由式（4）表示的阿托霉唑化合物。本发明提供的方法具有高转化率、高产品纯度、操作简便方便和环保友好等优点。
• PREPARATION METHOD FOR AZOXYSTROBIN
  申请人：NUTRICHEM COMPANY LIMITED

  公开号：US20160090365A1

  公开（公告）日：2016-03-31

  Disclosed in the present invention is a preparation method of azoxystrobin having a structure as shown by formula (1), the method comprising: a) performing an etherification reaction by reacting the compound having a structure shown by formula (2) with 2-cyanophenol and/or a salt thereof under the catalysis of an azabicyclo tertiary amine compound and/or a salt thereof as the catalyst in a butyl acetate medium to obtain a butyl acetate solution containing azoxystrobin; and b) cooling the butyl acetate solution containing azoxystrobin to precipitate Azoxystrobin having a structure as shown by formula (1) from the butyl acetate solution. Using the method provided by the present invention to prepare azoxystrobin can significantly improve the yield of azoxystrobin, and can obtain azoxystrobin products having high purity.

  本发明揭示了一种具有式（1）所示结构的氧化亚菌灵的制备方法，该方法包括：a）通过在丁酸丁酯介质中以氮杂双环三级胺化合物和/或其盐作为催化剂，将具有式（2）所示结构的化合物与2-氰基苯酚和/或其盐反应进行醚化反应，以获得含有氧化亚菌灵的丁酸丁酯溶液；和b）将含有氧化亚菌灵的丁酸丁酯溶液冷却，从丁酸丁酯溶液中沉淀具有式（1）所示结构的氧化亚菌灵。使用本发明提供的方法制备氧化亚菌灵可以显著提高氧化亚菌灵的产率，并可以获得高纯度的氧化亚菌灵产品。
• PREPARATION METHOD OF AZOXYSTROBIN
  申请人：Nutrichem Company Limited

  公开号：EP2998299A1

  公开（公告）日：2016-03-23

  Disclosed in the present invention is a preparation method of azoxystrobin having a structure as shown by formula (1), the method comprising: a) performing an etherification reaction by reacting the compound having a structure shown by formula (2) with 2-cyanophenol and/or a salt thereof under the catalysis of an azabicyclo tertiary amine compound and/or a salt thereof as the catalyst in a butyl acetate medium to obtain a butyl acetate solution containing azoxystrobin; and b) cooling the butyl acetate solution containing azoxystrobin to precipitate Azoxystrobin having a structure as shown by formula (1) from the butyl acetate solution. Using the method provided by the present invention to prepare azoxystrobin can significantly improve the yield of azoxystrobin, and can obtain azoxystrobin products having high purity.

  本发明公开了一种具有式（1）所示结构的唑啉草酯的制备方法，该方法包括：a) 在氮杂双环叔胺化合物和/或其盐作为催化剂的催化下，在乙酸丁酯介质中通过使具有式（2）所示结构的化合物与 2-氰基苯酚和/或其盐反应进行醚化反应，以获得含有唑啉草酯的乙酸丁酯溶液；以及 b) 冷却含有唑啉草酯的乙酸丁酯溶液，从乙酸丁酯溶液中析出具有式（1）所示结构的唑啉草酯。使用本发明提供的方法制备唑啉草酯可显著提高唑啉草酯的收率，并可获得高纯度的唑啉草酯产品。
• METHODS FOR PREPARING AZOXYSTROBIN AND INTERMEDIATE THEREOF
  申请人：Nutrichem Company Limited

  公开号：EP3042896A1

  公开（公告）日：2016-07-13

  The present invention discloses a method for preparing azoxystrobin intermediates represented by formulae (1) and (2), comprising: controlling a compound represented by formula (3) to contact with sodium methoxide and 4,6-dichloropyrimidine, to obtain a mixture of intermediates represented by formulae (1) and (2), in the existence of a catalyst, the catalyst is an azabicyclic compound or its salt. The present invention further discloses a method for preparing azoxystrobin, comprising: controlling the intermediate represented by formula (2) provided in the present invention to react with 2-cyanophenol or its salt under the catalytic action of an azabicyclic compound or its salt, to obtain an azoxystrobin compound represented by formula (4). The method provided in the present invention has advantages including high transformation ratio, high product purity, easy and convenient operation, and environmental friendliness.

  本发明公开了一种制备式(1)和(2)代表的唑菌酯中间体的方法，包括：控制式(3)代表的化合物与甲醇钠和4,6-二氯嘧啶接触，得到式(1)和(2)代表的中间体混合物，在存在催化剂的情况下，催化剂为氮杂环化合物或其盐。本发明进一步公开了一种制备唑啉草酯的方法，包括：控制本发明提供的式(2)代表的中间体在氮杂环化合物或其盐的催化作用下与2-氰基苯酚或其盐反应，得到式(4)代表的唑啉草酯化合物。本发明提供的方法具有转化率高、产品纯度高、操作简单方便、环保等优点。
• Method for preparing azoxystrobin and its intermediates
  申请人：Nutrichem Company Limited

  公开号：US10253001B2

  公开（公告）日：2019-04-09

  The present invention discloses a method for preparing azoxystrobin intermediates represented by formulae (1) and (2), comprising: controlling a compound represented by formula (3) to contact with sodium methoxide and 4,6-dichloropyrimidine, to obtain a mixture of intermediates represented by formulae (1) and (2), in the existence of a catalyst, the catalyst is an azabicyclic compound or its salt. The present invention further discloses a method for preparing azoxystrobin, comprising: controlling the intermediate represented by formula (2) provided in the present invention to react with 2-cyanophenol or its salt under the catalytic action of an azabicyclic compound or its salt, to obtain an azoxystrobin compound represented by formula (4). The method provided in the present invention has advantages including high transformation ratio, high product purity, easy and convenient operation, and environmental friendliness.

  本发明公开了一种制备式(1)和(2)代表的唑菌酯中间体的方法，包括：控制式(3)代表的化合物与甲醇钠和4,6-二氯嘧啶接触，得到式(1)和(2)代表的中间体混合物，在存在催化剂的情况下，催化剂为氮杂环化合物或其盐。本发明进一步公开了一种制备唑啉草酯的方法，包括：控制本发明提供的式(2)代表的中间体在氮杂环化合物或其盐的催化作用下与2-氰基苯酚或其盐反应，得到式(4)代表的唑啉草酯化合物。本发明提供的方法具有转化率高、产品纯度高、操作简单方便、环保等优点。