3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane | 14789-33-4

• 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: 3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane
• CAS: 14789-33-4
• 化学式: C₉H₁₈N₂
• 分子量: 154.255
• InChiKey: XVHVEMJNJDESBO-UHFFFAOYSA-N

物化性质

• 沸点：
  191.8±8.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tris(ethene)nickel(0) 、 3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane 以 乙醚 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  Applying the Macrocyclic Effect to Smaller Ring Structures. N,N‘-Dimethyl-3,7-diazabicyclo[3.3.1]nonane Nickel(0) Complexes

  摘要：

  The two N donor atoms in the tertiary diamine N,N'-dimethyl-3,7-diazabicyclo[3.3.1]nonane (dabn, C9H18N2) are ideally positioned in the bicyclic structure for chelation to a metal center. This feature was utilized to synthesize unusual diamine nickel(0)-ethene and -ethyne complexes, which represent limiting cases of the Pearson hard-soft acid-base concept. Thus, the reaction of Ni(C2H4)(3) With dabn affords yellow TP-3 (C9H18N2)Ni(C2H4) (1) (dec. 0 degrees C) in which the ethene ligand displays extreme high-field NMR shifts at delta(H) 0.27 and delta(C) 20.4 and an exceptionally small coupling constant (1)J(CH) = 142 Hz. Reaction of 1 with butadiene yields the red mononuclear T-4 complex (C9H18N2)Ni(eta(2)-C4H6)(2) (2a) in solution, from which the dinuclear derivative {(C9H18N2)Ni(eta(2)-C4H6)}(2)(mu-eta(2),eta(2)-C4H6) (2) (dec. 20 degrees C) is isolated. Complexes 2 and 2a are more soluble than 1 and thus better suited for further reactions. When ethyne is added to a solution of 2 or 2a at -78 degrees C, the yellow TP-3 complex (C9H18N2)Ni(C2H2) (3) (dec. -30 degrees C) is obtained. The ethyne ligand of 3 exhibits the lowest IR C=C stretching frequency (1560 cm(-1)) and by far the smallest NMR coupling constant (1)J(CH) = 178 Hz yet reported for a mononuclear nickel(0)-ethyne complex. In addition, Ni(CO)(4) reacts with dabn to yield orange T-4 (C9H18N2)Ni(CO)(2) (4) The results demonstrate that tertiary diamines, which are hard Lewis bases and which a priori are expected to coordinate poorly to the soft Lewis acid Ni(0), may be supported in such a coordination by the stabilizing principle of preorganization and consequently act as very powerful donor ligands.

  DOI：

  10.1021/ja971037v
• 作为产物：
  描述：

  3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-one 在 potassium hydroxide 、 肼 作用下， 以 乙二醇 为溶剂， 反应 16.0h， 以1 g的产率得到3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane
  参考文献：
  名称：

  原位红外光谱研究二胺连接的α-锂化氨基甲酸酯和苯甲酸酯的去质子生成和硼化

  摘要：

  二胺介导的 O-烷基氨基甲酸酯或苯甲酸酯与烷基锂试剂的 α-去质子化、用有机硼化合物捕获碳负离子以及所得硼酸盐络合物的 1,2-金属酸盐重排是有机硼化合物立体选择性同系化的主要步骤。虽然最后一步可以很容易地通过 11B 核磁共振光谱进行监测，但由于需要专门的分析技术，通常在低温下进行的前两个步骤不太为人所知。通过原位红外光谱对这些步骤的研究为优化有机硼化合物的同系化反应提供了宝贵的数据。虽然苯甲酸酯在非配位溶剂中的去质子化比在醚类溶剂中快，氨基甲酸酯的去质子化表现出相反的趋势，这种差异源于氨基甲酸酯与二胺连接的烷基锂试剂形成无活性寄生复合物的倾向。由于在硼-锂交换之前需要将硼上的二醇配体的氧原子与锂离子初始络合，因此在甲苯中大体积二胺配位的锂化物质的硼化反应非常缓慢。然而，醚溶剂或极少量的 THF 通过初始置换与锂离子配位的大体积二胺促进预络合。

  DOI：

  10.1021/jacs.8b06871

文献信息

• Methods for Treating Cognitive Disorders Using Inhibitors of Histone Deacetylase
  申请人：Forum Pharmaceuticals, Inc.

  公开号：US20170000749A1

  公开（公告）日：2017-01-05

  This disclosure relates to compounds for the inhibition of histone deacetylase and treatment of a cognitive disorder or deficit. More particularly, the disclosure provides for compounds of formula (I) wherein Q, J, L and Z are as defined in the specification.

  这份披露涉及用于抑制组蛋白去乙酰化酶和治疗认知障碍或缺陷的化合物。更具体地，该披露提供了公式（I）的化合物 其中 Q、J、L和Z如规范中所定义。
• Novel heteroaryl-diazabicycloalkanes
  申请人：——

  公开号：US20030004153A1

  公开（公告）日：2003-01-02

  The present invention relates to novel heteroaryl-diazabicycloalkanes which are found to be cholinergic ligands at the nicotinic Acetyl Choline Receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neurodegeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

  本发明涉及一种新型的杂环烷基二氮杂双环戊烷，发现其为烟碱乙酰胆碱受体的胆碱能配体。由于其药理特性，本发明的化合物可能对治疗与中枢神经系统（CNS）的胆碱能系统相关的疾病或紊乱，与平滑肌收缩相关的疾病或紊乱，内分泌疾病或紊乱，神经退行性疾病或紊乱，炎症相关的疾病或紊乱，疼痛以及由于滥用化学物质终止而引起的戒断症状等多种疾病或紊乱具有用处。
• Microwave-Assisted Raney Nickel Reduction of Bispidinone Thioketals to <i>N</i>,<i>N</i>′-Dialkylbispidines
  作者：Adolf Gogoll、Lauri Toom、Helena Grennberg

  DOI：10.1055/s-2006-942394

  日期：2006.6

  investigations into the properties of some 3,7-diazabicyclo[3.3.1]nonane (bispidine) derivatives are described. These compounds are structurally related to the naturally occurring lupanine alkaloids, they are of interest because of their cardiac antiarrhythmic function as well as their use as bases or ligands in organic chemical reactions. Their chemical properties are related to the presence of a rigid

  本论文介绍了一些3,7-二氮杂双环[3.3.1]壬烷（双吡啶）衍生物的改进合成和性质研究。这些化合物在结构上与天然存在的羽扇豆碱生物碱有关，由于它们的心脏抗心律失常功能以及它们在有机化学反应中作为碱或配体的用途而受到关注。它们的化学性质与具有两个氮原子的刚性分子支架的存在有关，该分子支架可用于与各种路易斯酸结合相互作用。已经开发了一种改进的合成方法，通过双吡啶酮提供双吡啶，同时避免使用高度有毒的肼，在替代方法中用作还原剂。一系列具有多种取代基的双吡啶衍生物的碱度为 13 个数量级。讨论了结构和碱度之间的相关性，并使用计算方法提出了具有更高碱度的其他衍生物。 几种双吡啶衍生物及其质子化形式的结构已通过 X 射线晶体学在固态和在溶液中使用 NMR 光谱学进行了表征. 已经研究了具有双吡啶配体的空间拥挤 (π-烯丙基) 钯配合物的结构和溶液动力学，揭示了对动态过程的机理洞察。使用体积庞大的双吡啶作为
• METHODS FOR TREATING COGNITIVE DISORDERS USING INHIBITORS OF HISTONE DEACETYLASE
  申请人：Rogers Kathryn

  公开号：US20110288070A1

  公开（公告）日：2011-11-24

  This disclosure relates to compounds for the inhibition of histone deacetylase and treatment of a cognitive disorder or deficit. More particularly, the disclosure provides for compounds of formula (I) wherein (I), Q, J, L and Z are as defined in the specification.

  本公开涉及化合物用于抑制组蛋白去乙酰化酶并治疗认知障碍或缺陷。更具体地，本公开提供了式（I）的化合物，其中（I），Q，J，L和Z如规范中所定义。
• Dibenzo[B,F][1,4]Oxazepin-11-yl-N-Hydroxybenzamides as HDAC Inhibitors
  申请人：Deziel Robert

  公开号：US20140011988A1

  公开（公告）日：2014-01-09

  This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula (I) wherein Q, J, L and Z are as defined in the specification.

  本发明涉及用于抑制组蛋白去乙酰化酶的化合物。更具体地，本发明提供了一种式（I）的化合物，其中Q、J、L和Z如规范中所定义。

表征谱图