3-乙烯基-1-氮杂双环[2.2.2]辛烷 | 2643-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 中文名称: 3-乙烯基-1-氮杂双环[2.2.2]辛烷
• 英文名称: 3-Vinylquinuclidine
• 英文别名: 3-vinyl-1-aza-bicyclo[2.2.2]octane；3-Vinylchinuclidin；3-Vinylquinuclidin；1-Azabicyclo[2.2.2]octane, 3-ethenyl-；3-ethenyl-1-azabicyclo[2.2.2]octane
• CAS: 2643-30-3
• 化学式: C₉H₁₅N
• 分子量: 137.225
• InChiKey: STMXRYQUMAMCAF-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C
• 沸点：
  85 °C(Press: 15 Torr)
• 密度：
  0.9409 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-乙烯基-1-氮杂双环[2.2.2]辛烷 、 二苯甲酮 生成 3-(3',3'-Diphenyl-3'-oxy-1'-propinyl)quinuclidine
  参考文献：
  名称：

  LIBMAN N. M.; KUZNETSOV S. G.; GORCHAKOV V. S.; GOLIKOV S. N.; LEBEDEVA D+, XIM.-FARMATS. ZH., 20,(1986) N 11, 1308-1312

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氮杂双环[2.2.2]辛烷-3-羧醛 、 甲基三苯基碘化鏻 在 sodium amide 作用下， 生成 3-乙烯基-1-氮杂双环[2.2.2]辛烷
  参考文献：
  名称：

  Amino alcohols of the acetylene series. IX. 3,3-Diphenyl-3-oxypropinyl-substituted quinuclidines

  摘要：

  DOI：

  10.1007/bf00763694

文献信息

• COMPLEX AND STRUCTURALLY DIVERSE COMPOUNDS
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20150274638A1

  公开（公告）日：2015-10-01

  The invention provides a novel, general, and facile strategy for the creation of small molecules with high structural and stereochemical complexity. Aspects of the methods include ring system distortion reactions that are systematically applied to rapidly convert readily available natural products to structurally complex compounds with diverse molecular architectures. Through evaluation of chemical properties including fraction of sp 3 carbons, ClogP, and the number of stereogenic centers, these compounds are shown to be significantly more complex and diverse than those in standard screening collections. This approach is demonstrated with natural products (gibberellic acid, adrenosterone, and quinine) from three different structural classes, and methods are described for the application of this strategy to any suitable natural product.

  这项发明提供了一种新颖、通用且简便的策略，用于创造具有高结构和立体化学复杂性的小分子。该方法的方面包括系统地应用于快速将易得的天然产物转化为具有多样分子结构的结构复杂化合物的环系统失真反应。通过评估化学性质，包括sp3碳的分数、ClogP和立体中心的数量，这些化合物被证明比标准筛选集合中的化合物显着更复杂和多样化。这种方法是通过来自三个不同结构类别的天然产物（赤霉酸、肾上腺酮和奎宁）来展示的，并描述了将该策略应用于任何合适的天然产物的方法。
• VINYL QUINUCLIDINE USEFUL AS A SYNTHESIS INTERMEDIATE IN THE PREPARATION OF (R)-MEQUITAZINE
  申请人：Nicolas Marc

  公开号：US20130296553A1

  公开（公告）日：2013-11-07

  The present invention relates to the use of the vinyl quinuclidine enantiomer (R) of the following formula 2 as a synthesis intermediate in the preparation of (R)-mequitazine.

  本发明涉及使用以下式子2的乙烯喹诺啉（R）对映体作为合成(R)-美奎嗪的中间体。
• Quinuclidine derivatives as squalene synthase inhibitors
  申请人：Zeneca Limited

  公开号：US05714496A1

  公开（公告）日：1998-02-03

  Compounds of formula (I) and their pharmaceutically acceptable salts in which R.sup.1 is hydrogen or hydroxy; R.sup.2 is hydrogen; or R.sup.1 and R.sup.2 are joined together so that CR.sup.1 -CR.sup.2 is a double bond; X is selected from --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --CH.sub.2 O--, --CH.sub.2 NH--, --NHCH.sub.2 --, --CH.sub.2 CO--, --COCH.sub.2 --, --CH.sub.2 S-- and --SCH.sub.2 --; Ar.sup.1 is a phenylene moiety; Ar.sup.2 is a heteroaryl moiety; and wherein one or both of Ar.sup.1 and Ar.sup.2 may optionally bear one or more substituents independently selected from halogeno, hydroxy, amino, nitro, cyano, carboxy, carbamoyl, alkyl, alkenyl, alkynyl, alkoxy, alkylamino, di-alkylamino, N-alkylcarbamoyl, di-N,N-alkylcarbamoyl, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, halogeno-alkyl, carboxyalkyl and alkanoylamino; provided that when R.sup.1 is hydroxy, X is not selected from --NHCH.sub.2 -- and --SCH.sub.2 --; are inhibitors of squalene synthase and hence useful in treating medical conditions in which a lowering of cholesterol is beneficial, such as hypercholesterolemia and atherosclerosis. Processes for preparing these derivatives, pharmaceutical compositions containing them are also described together with their use in medicine.

  化合物的化学式为（I），其药学上可接受的盐，其中R.sup.1是氢或羟基；R.sup.2是氢；或者R.sup.1和R.sup.2连接在一起，使得CR.sup.1-CR.sup.2是双键；X从--CH.sub.2 CH.sub.2 --，--CH.dbd.CH--，--C.tbd.C--，--CH.sub.2 O--，--CH.sub.2 NH--，--NHCH.sub.2 --，--CH.sub.2 CO--，--COCH.sub.2 --，--CH.sub.2 S--和--SCH.sub.2 --中选择；Ar.sup.1是苯基；Ar.sup.2是杂环芳基；其中Ar.sup.1和Ar.sup.2中的一个或两个可以选择性地带有一个或多个取代基，这些取代基独立地选择自卤素，羟基，氨基，硝基，氰基，羧基，氨基甲酰基，烷基，烯基，炔基，烷氧基，烷基氨基，双烷基氨基，N-烷基氨基甲酰基，双N，N-烷基氨基甲酰基，烷氧羰基，烷基硫基，烷基亚砜基，烷基磺酰基，卤代烷基，羧基烷基和脂肪酰胺基；但当R.sup.1是羟基时，X不选择自--NHCH.sub.2--和--SCH.sub.2--；这些化合物是角鲨烷合酶的抑制剂，因此可用于治疗降低胆固醇有益的医疗状况，如高胆固醇血症和动脉硬化。还描述了制备这些衍生物的过程，含有它们的制药组合物以及它们在医学上的应用。
• Complex and structurally diverse compounds
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US10081592B2

  公开（公告）日：2018-09-25

  The invention a novel, general, and facile strategy for the creation of small molecules with high structural and stereochemical complexity. Aspects of the methods include ring system distortion reactions that are systematically applied to rapidly convert readily available natural products to structurally complex compounds with diverse molecular architectures. Through evaluation of chemical properties including fraction of sp3 carbons, ClogP, and the number of stereogenic centers, these compounds are shown to be significantly more complex and diverse than those in standard screening collections. This approach is demonstrated with natural products (gibberellic acid, adrenosterone, and quinine) from three different structural classes, and methods are described for the application of this strategy to any suitable natural product.

  本发明是一种新颖、通用和简便的策略，用于制造结构和立体化学复杂性高的小分子。该方法的各个方面包括系统地应用环系畸变反应，将容易获得的天然产物快速转化为具有不同分子结构的结构复杂的化合物。通过对化学特性（包括 sp3 碳的比例、ClogP 和立体中心的数量）进行评估，这些化合物的复杂性和多样性明显高于标准筛选集合中的化合物。该方法通过三种不同结构类别的天然产物（赤霉素、肾上腺甾酮和奎宁）进行了演示，并介绍了将该策略应用于任何合适的天然产物的方法。
• Ernest, Collection of Czechoslovak Chemical Communications, 1950, vol. 15, p. 486,488
  作者：Ernest

  DOI：——

  日期：——