5-氮杂金刚烷-2-酮 | 42949-24-6

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 5-氮杂金刚烷-2-酮
• 中文别名: 1-氮杂三环[3.3.1.13,7]-4-癸酮
• 英文名称: 1-azaadamantane-4-one
• 英文别名: 1-azatricyclo[3.3.1.13,7 ]decane-4-one；1-azatricyclo<3.3.1.1^3,7>decan-4-one；1-azatricyclo[3.3.1.1(3,7)]decan-4-one；4-oxo-1-azaadamantane；1-azaadamantan-4-one；5-azaadamantan-2-one；1-Azatricyclo[3.3.1.13,7]decan-4-one
• CAS: 42949-24-6
• 化学式: C₉H₁₃NO
• mdl: MFCD12545907
• 分子量: 151.208
• InChiKey: XGZKYPXTXBKQTM-UHFFFAOYSA-N

物化性质

• 沸点：
  265 ºC
• 密度：
  1.19
• 闪点：
  106 ºC

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-氮杂金刚烷-2-酮 在 potassium tert-butylate 、 肼 作用下， 以 xylene 为溶剂， 反应 1.5h， 生成 1-氮杂三环[3.3.1.1(3,7)]癸烷
  参考文献：
  名称：

  Face Selection in Additions to the Trigonal C2 Site in Quaternized 5-Azaadamantane Derivatives

  摘要：

  The quaternary N-allyl bromide salt 5 of allyl alpha-[2-(5-azaadamantylidene)]benzyl ether upon warming gave the Claisen rearrangement products 6 is the ratio E/Z = 93:7. The epoxidation of the N-oxide 8 of 2-methylene-5-azaadamantane 7 with m-CPBA gives rise to the two diastereomeric epoxides 9 in the ratio E/Z = 19:81. Reaction of the methyl iodide salt of this olefin with bromine in water produces the E- and Z-dibromides 10 in the ratio 74:26 as well as the corresponding glycols 12 in the ratio 86:14. The same reaction in methanol gives the E- and Z-isomers of 10 alone, in the ratio of 35:65. The interpretation is that, in all of these reactions, the trigonal carbon preferably undergoes addition at that face which is antiperiplanar to the more electron-rich vicinal bonds, and does so by margins substantially in excess of those observed with the corresponding 5-fluoroadamantanes. This fact lends further strength to our previously drawn conclusion that hyperconjugative transition state stabilization is the principal factor in the electronic component of face selection.

  DOI：

  10.1021/ja00151a005
• 作为产物：
  描述：

  聚合甲醛 、 1,4-二氧杂螺[4.5]癸烷-8-甲胺 在 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以56%的产率得到5-氮杂金刚烷-2-酮
  参考文献：
  名称：

  A Simple Synthesis of 1-Azaadamantan-4-one

  摘要：

  DOI：

  10.1055/s-1981-29617

文献信息

• [EN] PROGRANULIN MODULATORS AND METHODS OF USING THE SAME<br/>[FR] MODULATEURS DE LA PROGRANULINE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ARKUDA THERAPEUTICS

  公开号：WO2020252222A1

  公开（公告）日：2020-12-17

  Provided herein are compounds that modulate progranulin and methods of using the compounds in progranulin-associated disorders, such as Frontotemporal dementia (FTD).

  本文件提供了调节颗粒蛋白的化合物及其在颗粒蛋白相关疾病中的使用方法，例如额颞痴呆（FTD）。
• [EN] SPIRO-OXADIAZOLINE COMPOUNDS AS AGONISTS OF α-7-NICOTINIC ACETYLCHOLINE RECEPTORS<br/>[FR] COMPOSÉS SPIRO-OXADIAZOLINE EN TANT QU'AGONISTES DES RÉCEPTEURS DE L'ACÉTYLCHOLINE Α-7 NICOTINIQUE
  申请人：FORUM PHARMACEUTICALS INC

  公开号：WO2015066371A1

  公开（公告）日：2015-05-07

  The present invention relates to novel spiro-oxadiazoline compounds that are suitable as agonists or partial agonists of a7-nAChR, and pharmaceutical compositions of the same, methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering a spiro-oxadiazoline cx7-nAChR agonist or partial agonist, to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

  本发明涉及新型螺环-噁二唑啉化合物，适用作a7-nAChR的激动剂或部分激动剂，以及这些化合物和组合物的制备方法、药物组合物，以及在维持、治疗和/或改善认知功能的方法中使用这些化合物和组合物。具体而言，涉及向需要的患者（例如患有认知缺陷和/或希望增强认知功能的患者）施用螺环-噁二唑啉cx7-nAChR激动剂或部分激动剂的方法，以使其获益。
• COMPOUNDS CONTAINING AN ALICYCLIE STRUCTURE AND ANTI-TUMOR APPLICATION
  申请人：Xu Lifeng

  公开号：US20140045779A1

  公开（公告）日：2014-02-13

  This invention relates with anti-tumor activities of new compounds containing an adamantyl group or analogs thereof. The invention also relates with the medication applications of anti-tumor and other diseases by this kind of compounds with the combination of S, P, T structures containing adamantyl group and the formation of stereoisomer, tautomers, prodrug, pharmaceutically acceptable salts, complex salts or solvates to their anticancer application and anticancer agents, which have the following general formula:

  这项发明涉及含有金刚烷基团或其类似物的新化合物的抗肿瘤活性。该发明还涉及利用这种含有金刚烷基团的S、P、T结构的化合物与立体异构体、互变异构体、前药、药用盐、复杂盐或溶剂化物的结合来治疗抗肿瘤和其他疾病的药物应用，这些抗肿瘤剂具有以下一般公式：
• Role of the nitrogen atom in the complex metal hydride reduction of unhindered γ-azacyclohexanones
  作者：Yasuhisa Senda、Masayuki Morita、Hiroki Itoh

  DOI：10.1039/p29960000221

  日期：——

  axial position. The appreciable solvent effect apparent in the NaBH4 reduction of 1-azaadamantan-4-one may be responsible for the hydrogen bond formation of the nN orbital with the protic solvent. The stereochemistry of the complex metal hydride reduction of γ-azacyclohexanones could be explained by the difference in the non-bonding two electron stabilisation between the incipient σ‡* bond and the antiperiplanar

  优先氢化攻击已经发现在发生连接面，这是相反的一侧到γ-氮原子，在的LiAlH羰基的4还原1- azaadamantan -4-酮，其n个Ñ轨道处于赤道位置。另一方面，氢化物的侵蚀主要从n N轨道位于轴向位置的1,2-二甲基哌啶-4-酮和2-酮喹啉叠氮的轴向发生。NaBH 4还原1-zazaadamantan-4-one中明显的溶剂作用可能是n N氢键形成的原因与质子溶剂一起进入轨道。复合金属氢化物还原γ-azacyclohexanones的立体化学可以通过在初始σ之间的非键合二个电子稳定的差异进行说明‡ *键和antiperiplanar烯丙基σ我其通过贯通空间和扰动键/或与远程杂原子的键合相互作用。
• DIAZAHOMOADAMANTANE DERIVATIVES AND METHODS OF USE THEREOF
  申请人：Schrimpf Michael R.

  公开号：US20100324027A1

  公开（公告）日：2010-12-23

  The invention relates to compounds that are diazahomoadamantane derivatives, compositions comprising such compounds, and methods of using such compounds and compositions.

  该发明涉及一种二氮杂同戊二烷衍生物，包括该类化合物的组合物，以及使用该类化合物和组合物的方法。

表征谱图