1-(adamantan-2-yl)piperazine | 57942-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(adamantan-2-yl)piperazine
• 英文别名: N-(2-Adamantyl)-piperazin；1-(2-Adamantyl)piperazine
• CAS: 57942-77-5
• 化学式: C₁₄H₂₄N₂
• mdl: MFCD02056458
• 分子量: 220.358
• InChiKey: LBXYGEXAYYPYSE-UHFFFAOYSA-N

物化性质

• 熔点：
  71-73 °C (sublm)
• 沸点：
  314.0±10.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-碘吡啶 、 1-(adamantan-2-yl)piperazine 在 copper(l) iodide 、 2-(2-甲基-1-氧代丙烷)环己酮 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以34%的产率得到1-(adamantan-2-yl)-4-(pyridin-2-yl)piperazine
  参考文献：
  名称：

  Arylation of adamantanamines: VII. Copper(I)-catalyzed N-heteroarylation of adamantane-containing amines with halopyridines

  摘要：

  Copper(I)-catalyzed N-heteroarylation of a wide series of adamantane-containing amines with 2-bromo- and 2- and 3-iodopyridines was studied. The corresponding N-pyridyl derivatives were formed in all cases, but iodopyridines were considerably more reactive. The best results were obtained with the catalytic system CuI-2-(2-methyl-1-oxopropyl)cyclohexanone-DMF which ensured up to 90% yield of the target products. The yield of N-pyridyl derivatives also depended on the steric environment of the amino group in the initial adamantane-containing amine. The yield of the heteroarylation products can be considerably increased using excess iodopyridine. The reaction of 2-(adamantan-1-yl)ethanamine with 2,6-dibromopyridine successfully afforded the corresponding diamine, and N,N'-dipyridyl derivatives were obtained in high yields from 2,2'-(adamantane-1,3-diyl)diethanamine.

  DOI：

  10.1134/s1070428015030021
• 作为产物：
  描述：

  3-[2-(2-adamantylamino)ethyl]-1,3-oxazolidin-2-one 在 氢溴酸 作用下， 生成 1-(adamantan-2-yl)piperazine
  参考文献：
  名称：

  使用2-恶唑烷酮作为潜在的氮丙啶等效物。三，N-取代的哌嗪的制备

  摘要：

  由各种取代的2-恶唑烷酮衍生物3制备了许多N-芳基和N-烷基取代的哌嗪1。该方法包括在冰醋酸中用HBr处理3，然后在醇溶剂中加热所得的开环盐5。通过结晶分离出哌嗪1a-1q，产率为23-91％。

  DOI：

  10.1016/0040-4039(94)85306-1

文献信息

• Inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme
  申请人：Link T. James

  公开号：US20050277647A1

  公开（公告）日：2005-12-15

  The present invention relates to compounds which are inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme. The present invention further relates to the use of inhibitors of 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme for the treatment of non-insulin dependent type 2 diabetes, insulin resistance, obesity, lipid disorders, metabolic syndrome, and other diseases and conditions that are mediated by excessive glucocorticoid action.

  本发明涉及抑制11-β-羟基类固醇脱氢酶1型酶的化合物。本发明还涉及利用11-β-羟基类固醇脱氢酶1型酶的抑制剂治疗非胰岛素依赖型2型糖尿病、胰岛素抵抗、肥胖、脂质紊乱、代谢综合征以及其他由过度糖皮质激素作用介导的疾病和症状。
• [EN] COVALENT TARGETING OF E3 LIGASES<br/>[FR] CIBLAGE COVALENT DES LIGASES E3
  申请人：UNIV CALIFORNIA

  公开号：WO2020076996A1

  公开（公告）日：2020-04-16

  Disclosed herein, inter alia, are compositions and methods for targeting E3 ligases. In an aspect is a targeted protein degrader including 1) a targeted protein binder and 2) an E3 Ubiquitin ligase binder, wherein the E3 Ubiquitin ligase is human RNF4 or human RNF114. In an aspect is provided a pharmaceutical composition including a compound as described herein, including embodiments, and a pharmaceutically acceptable excipient.

  本公开的内容包括针对E3连接酶的组合物和方法。一个方面涉及一种靶向蛋白降解剂，包括1）靶向蛋白结合物和2）E3泛素连接酶结合物，其中E3泛素连接酶为人类RNF4或人类RNF114。另一方面提供了一种包括本文所述化合物的药物组合物，包括实施例和药用可接受的赋形剂。
• Amination of chloro-substituted heteroarenes with adamantane-containing amines
  作者：A. S. Abel、O. K. Grigorova、A. D. Averin、O. A. Maloshitskaya、G. M. Butov、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1007/s11172-016-1516-7

  日期：2016.7

  adamantane-containing amines characterized by different steric hindrances at the amino group was studied. The yields of the amination products depended on the structure of starting compounds. In the reactions of all the dichloroheteroarenes, selective substitution of only one chlorine atom took place, with the best yields being observed for 2,6-dichloropyrazine. In the reaction of 1,3-dichloroisoquinoline

  研究了 3,6-二氯哒嗪、氯吡嗪、2,3 和 2,6-二氯吡嗪、2-氯喹喔啉、1-氯和 1,3-二氯异喹啉与各种含金刚烷胺的胺化反应，这些胺的特征在于氨基具有不同的空间位阻。胺化产物的产率取决于起始化合物的结构。在所有二氯杂芳烃的反应中，仅发生一个氯原子的选择性取代，2,6-二氯吡嗪的产率最高。在 1,3-二氯异喹啉的反应中，1 位的氯原子被选择性取代，产率高达 90%。
• Synthesis and assessment of 4-aminotetrahydroquinazoline derivatives as tick-borne encephalitis virus reproduction inhibitors
  作者：Kseniya N. Sedenkova、Evgenia V. Dueva、Elena B. Averina、Yuri K. Grishin、Dmitry I. Osolodkin、Liubov I. Kozlovskaya、Vladimir A. Palyulin、Evgenii N. Savelyev、Boris S. Orlinson、Ivan A. Novakov、Gennady M. Butov、Tamara S. Kuznetsova、Galina G. Karganova、Nikolay S. Zefirov

  DOI：10.1039/c4ob02649g

  日期：——

  obtained and their activity against tick-borne encephalitis virus reproduction was studied. Nine compounds were found to inhibit TBEV entry into the host cells. A bulky hydrophobic adamantyl group was identified to be important for the antiviral activity. The developed synthetic route allowed an easy access to a consistent compound library for further structure-activity relationship studies.

  属于黄病毒属的传脑炎病毒（TBEV）在人类中引起严重感染。寻找针对TBEV的治疗相关化合物需要探索新的化学型。描述了基于氟取代的杂环核的先前未知的4-氨基嘧啶和4-氨基嘧啶N-氧化物的通用合成。获得了具有代表性的一系列4-氨基四氢喹唑啉衍生物，它们含有脂肪族和芳香族取代基以及金刚烷骨架，并研究了它们对tick传脑炎病毒繁殖的活性。发现九种化合物抑制TBEV进入宿主细胞。庞大的疏水性金刚烷基被确定对于抗病毒活性很重要。
• Catalyst-free amination of 2-fluoropyridine and 2-fluoro-5-halopyridines with adamantane amines
  作者：A. S. Abel、O. K. Grigorova、A. D. Averin、O. A. Maloshitskaya、O. A. Popov、G. M. Butov、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1007/s11172-015-0919-1

  日期：2015.3

  Catalyst-free reactions of 2-fluoropyridine with amines and diamines bearing the adamantyl moiety at either the N atom or in the side chain were studied. Amines, which do not contain secondary alkyl substituents at the amino group, react with an excess of 2-fluoropyridine to give N-(pyridin-2-yl) derivatives in the yields from moderate to good. 2-Fluoro-5-halopyridines were found to be more reactive

  研究了 2-氟吡啶与在 N 原子或侧链中带有金刚烷基部分的胺和二胺的无催化剂反应。在氨基上不含仲烷基取代基的胺与过量的 2-氟吡啶反应生成 N-(吡啶-2-基)衍生物，产率从中等到高。发现 2-氟-5-卤代吡啶比 2-氟吡啶更具反应性。