2-Methyl-2-aza-bicyclo<2.2.2>octan-3-on | 4029-24-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-Methyl-2-aza-bicyclo<2.2.2>octan-3-on
• 英文别名: 2-Azabicyclo[2,2,2]-octanone-3, 2-methyl-；2-methyl-2-azabicyclo[2.2.2]octan-3-one
• CAS: 4029-24-7
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: KQLBOVYGRJPZHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Methyl-2-aza-bicyclo<2.2.2>octan-3-on 在 lithium aluminium tetrahydride 作用下， 生成 2-methyl-2-azabicyclo<2.2.2>octane
  参考文献：
  名称：

  Nitrogen Inversion Barrier of 2-Methyl-2-azabicyclo[2.2.1]heptane. The Role of Torsional Strain in Pyramidal Inversion

  摘要：

  Low-temperature C-13 NMR measurements indicate that the endo isomer of 2-methyl-2-azabicyclo-[2.2.1]heptane is about 0.3 kcal mol(-1) more stable than the exo isomer. Rate constants for inversion from the endo to exo isomer were determined by NMR line shape analysis. The inversion barrier, Delta G(double dagger), of 7.2 kcal mol(-1) is lower than that in model acyclic amines, despite an internal CNC bond angle that is less than the tetrahedral angle of 109.47 degrees. Comparison with 7-methyl-7-azabicyclo-[2.2.1]heptane that has a small internal CNC angle and an unusually high barrier, as well as other cyclic and bicyclic amines, leads to the conclusion that torsional (eclipsing) strain plays a significant role along with angle strain in determining inversion barriers. Molecular mechanics calculations of the change in energy between pyramidal ground state and planar transition state account reasonably well for the observed barriers. New measurements of inversion barriers and their dependence on solvent are also reported for 2-methyl-2-azabicyclo[2.2.2]octane and 1-methyl-4-piperidone.

  DOI：

  10.1021/jo951940i
• 作为产物：
  描述：

  4-甲氨基苯甲酸 在 氢气 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以23 g (75%)的产率得到4-(methylamino)cyclohexanecarboxylic acid
  参考文献：
  名称：

  Biologically active heterobicyclic hydroximidates and

  摘要：

  描述了Formula I的新异双环化合物，以及制备这些化合物和杀虫剂组合物的方法。

  公开号：

  US04424213A1

文献信息

• NMR and Raman spectroscopic study of complex formation between 2-methyl-2-azabicyclo-[2,2,2] -octa-3-one and TiCl4
  作者：J. Lövy、J. Štokr、D. Doskočilová、R. Puffr、J. Dybal、B. Schneider

  DOI：10.1016/0022-2860(80)80263-8

  日期：1980.11

  Abstract From analysis of 1 H and 13 C NMR and Raman spectroscopic data, in CDCl 3 and 1,1,2,2-tetrachloroethane- d 2 solution, the lactam 2-methyl-2-azabicyclo-[2,2,2]-octa-3-one (L) was found to form complexes with TiCl 4 (M) of overall composition M 2 L, ML and ML 2 . Two forms of the ML 2 complex were observed by NMR. In all these complexes, Ti coordinates to the carbonyl oxygen, and the metal—carbonyl

  摘要 从 1 H 和 13 C NMR 和拉曼光谱数据分析，在CDCl 3 和1,1,2,2-四氯乙烷-d 2 溶液中，内酰胺2-甲基-2-氮杂双环-[2,2,2]发现 -octa-3-one (L) 与 TiCl 4 (M) 形成复合物，其总组成为 M 2 L、ML 和 ML 2 。通过NMR观察到ML 2 复合物的两种形式。在所有这些配合物中，Ti 与羰基氧配位，并且金属-羰基键是相同类型的。配合物 ML 和 ML 2 含有六配位的 Ti；在 M 2 L 中，配位数可能是五。ML 2 配合物和未配合形式之间的内酰胺交换动力学已被表征，并提出了四种配合物的结构。
• [EN] 2-AZA-BICYCLO[2.2.2]OCTANE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS 2-AZA-BICYCLO[2.2.2]OCTANE ET LEURS UTILISATIONS
  申请人：ASTRAZENECA AB

  公开号：WO2010087761A1

  公开（公告）日：2010-08-05

  This invention relates to 2-aza-bicyclo [2.2.2] octane compounds (and salts thereof), the process for making such a compound and pharmaceutical compositions comprising such a compound. The invention also relates to the use of the compounds for modulating the glycine transporter 1 (GIyTl) and for the treatment of psychosis, cognitive disorders, bipolar disorders, depression disorders, anxiety disorders, posttraumatic stress disorders and pain.

  这项发明涉及2-aza-bicyclo [2.2.2]辛烷化合物（及其盐），制备这种化合物的过程以及包含这种化合物的药物组合物。该发明还涉及利用这些化合物调节甘氨酸转运蛋白1（GIyTl）并用于治疗精神病、认知障碍、双相情感障碍、抑郁症、焦虑症、创伤后应激障碍和疼痛。
• Nitrogen-Containing Heterocyclyl Substituted Imidazoquinolines and Imidazonaphthyridines
  申请人：Merrill A. Bryon

  公开号：US20070213356A1

  公开（公告）日：2007-09-13

  Imidazoquinoline and imidazonaphthyridine compounds having a nitrogen-containing heterocyclyl substituent at the 5-, 6-, 7-, or 8-position, pharmaceutical compositions containing the compounds, intermediates, and methods of making and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本发明涉及在5-、6-、7-或8-位置具有含氮杂环基取代基的咪唑喹啉和咪唑萘啶化合物，含有这些化合物的制药组合物、中间体以及制备和使用这些化合物作为免疫调节剂、在动物中调节细胞因子生物合成以及用于治疗包括病毒性和肿瘤性疾病的方法。
• LACTAM CONTAINING CYCLIC DIAMINES AND DERIVATIVES AS FACTOR XA INHIBITORS
  申请人：Qiao X Jennifer

  公开号：US20070135428A1

  公开（公告）日：2007-06-14

  The present application describes lactam-containing cyclic diamines and derivatives thereof of Formula I: P 4 -M-M 4 I or pharmaceutically acceptable salt forms thereof, wherein M is a non-aromatic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了公式I：P4-M-M4I或其药学上可接受的盐形式的含有内酰胺的环状二胺及其衍生物，其中M为非芳香族碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶的抑制剂，特别是Xa因子的抑制剂。
• Biologically active heterobicyclic hydroximidates and thiolhydroximidates and carbamate ester derivatives thereof
  申请人：SDS BIOTECH CORPORATION

  公开号：EP0051990B1

  公开（公告）日：1986-01-02