1-(1-金刚烷)吡咯烷-2-酮 | 3716-62-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(1-金刚烷)吡咯烷-2-酮
• 英文名称: N-adamantyl-α-pyrrolidone
• 英文别名: N-(1-Adamantyl)-2-pyrrolidone；1-(1-adamantyl)pyrrolidone；1-(adamant-1-yl)pyrrolidin-2-one；1-(1-Adamantanyl)-2-pyrrolidinon；1-adamantan-1-yl-pyrrolidin-2-one；1-(1-Adamantyl)pyrrolidin-2-one
• CAS: 3716-62-9
• 化学式: C₁₄H₂₁NO
• mdl: MFCD01749832
• 分子量: 219.327
• InChiKey: MLSPGERYUBJGGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  1-(1-金刚烷)吡咯烷-2-酮 在 硫酸 、 硝酸 作用下， 以56.3%的产率得到N-(1-Hydroxy-3-adamantyl)-2-pyrrolidone
  参考文献：
  名称：

  N-adamantyl derivatives of pyrrolidone and their biological activity

  摘要：

  DOI：

  10.1007/bf00772156
• 作为产物：
  描述：

  γ-丁内酯 、 金刚烷胺 反应 3.0h， 以86.5%的产率得到1-(1-金刚烷)吡咯烷-2-酮
  参考文献：
  名称：

  N-adamantyl derivatives of pyrrolidone and their biological activity

  摘要：

  DOI：

  10.1007/bf00772156

文献信息

• [EN] ADAMANTYL PYRROLIDIN-2-ONE DERIVATIVES AS 11-BETA HYDROXYSTEROID DEHYDROGENASE INHIBITORS<br/>[FR] UTILISATION DE DERIVES D'ADAMANTYLE PYRROLIDIN-2-ONE COMME INHIBITEURS DE LA 11-BETA-HYDROXYSTEROIDE DESHYDROGENASE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005108361A1

  公开（公告）日：2005-11-17

  The N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein n is 1 or 2; M represents a direct bond or a C1-3alkyl linker optionally substituted with one or two substituents selected from C1-4alkyl, C1-3alkyloxy-C1-4alkyl-, hydroxy-C1-4alkyl-, hydroxy, C1-3alkyloxy- or phenyl-C1-4alkyl-; R1 and R2 each independently represent hydrogen, halo, cyano, hydroxy, Cl-4alkyl optionally substituted with halo, C1-4alkyloxy- optionally substituted with one or where possible two or three substituents selected from hydroxy, Ar1 and halo ; R3 represents hydrogen, halo, C1-4alkyl, C1-4alkyloxy-, cyano or hydroxy; R4 represents hydrogen, halo, Cl-4alkyl, hydroxy, cyano or C1-4alkyloxy- optionally substituted with one or where possible two or three substituents selected from hydroxy and halo; R5 represents hydrogen, C1-4alkyl or Ar2-C1-4alkyl-; R6 represents hydrogen, hydroxy, halo, C1-4alkyl or C1-4alkyoxy-; R7 represents hydrogen or R7 and R5 taken together with the carbon atom to which they are attached from a -C2-alkyl- linker; Ar1 and Ar2 each independently represent phenyl or naphtyl wherein said phenyl and naphtyl are optionally substituted with C1-4alkyl, C1-4alkyloxy-, or phenyl-C1-4alkyl.

  N-氧化物形式，药学上可接受的加合盐及其立体化异构体形式，其中n为1或2；M代表直接键或C1-3烷基连接物，可选地取代为从C1-4烷基、C1-3烷氧基-C1-4烷基、羟基-C1-4烷基、羟基、C1-3烷氧基或苯基-C1-4烷基中选择的一个或两个取代基；R1和R2各自独立地代表氢、卤素、氰基、羟基、Cl-4烷基，可选地取代为卤素、C1-4烷氧基，可选地取代为从羟基、Ar1和卤素中选择的一个或多个取代基；R3代表氢、卤素、C1-4烷基、C1-4烷氧基、氰基或羟基；R4代表氢、卤素、Cl-4烷基、羟基、氰基或C1-4烷氧基，可选地取代为从羟基和卤素中选择的一个或多个取代基；R5代表氢、C1-4烷基或Ar2-C1-4烷基；R6代表氢、羟基、卤素、C1-4烷基或C1-4烷氧基；R7代表氢或R7和R5一起与它们连接的碳原子形成-C2-烷基连接物；Ar1和Ar2各自独立地代表苯或萘基，其中所述苯和萘基可选地取代为C1-4烷基、C1-4烷氧基或苯基-C1-4烷基。
• CYCLOHEXYLPYRAZOLE-LACTAM DERIVATIVES AS INHIBITORS OF 11-BETA-HYDROXYSTEROID DEHYDROGENASE 1
  申请人：Aicher Thomas Daniel

  公开号：US20090111800A1

  公开（公告）日：2009-04-30

  The present invention discloses novel compounds of Formula (I): having 11β-HSD type 1 antagonist activity, as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula (I), as well as methods of using the compounds and compositions to treat diabetes, hyperglycemia, obesity, hypertension, hyperlipidemia, metabolic syndrome, and other conditions associated with 11β-HSD type 1 activity.

  本发明公开了具有11β-HSD类型1拮抗活性的Formula (I)的新化合物，以及制备这种化合物的方法。在另一实施例中，该发明公开了包含Formula (I)化合物的药物组合物，以及利用这些化合物和组合物治疗糖尿病、高血糖、肥胖、高血压、高脂血症、代谢综合征以及与11β-HSD类型1活性相关的其他疾病的方法。
• Synthesis of adamantane derivatives. LVIII. Reaction of 1-adamantyl chloride with some heterocyclic unsaturated silanes.
  作者：TADASHI SASAKI、AKIRA NAKANISHI、MASATOMI OHNO

  DOI：10.1248/cpb.30.2051

  日期：——

  Various silylated heterocycles having amide functionality were treated with 1-adamantyl chloride (1) in the presence of a Lewis acid to give the corresponding N-adamantylated heterocycles. If α-position to the reacting lactim nitrogen was substituted, the reaction no longer occurred, or the adamantylation occurred at the position other than the expected nitrogen. These facts are attributed to a steric blocking effect of the α-substituent. While the same treatment of the thioamide 46 gave the S-adamantylated product, 48 and 51 afforded in contrast the N- and S-adamantylated products, respectively ; this result can be explained in terms of steric effect. Analogously, silylated 2-pyrazolines and triazoles were adamantylated at nitrogen. The reactions of 2-trimethylsilylthiophene, furan and -pyridine with 1 failed to give site-selective monoadamantylation.

  在路易斯酸存在下，用 1-金刚烷酰氯（1）处理各种具有酰胺官能团的硅烷化杂环，得到相应的 N-金刚烷化杂环。如果反应的内酰胺氮的α位被取代，则不再发生反应，或者在预期氮以外的位置发生金刚烷基化反应。这些情况都归因于 α 取代基的立体阻滞效应。同样处理硫代酰胺 46 得到的是 S-金刚烷化产物，而 48 和 51 则分别得到了 N-和 S-金刚烷化产物；这一结果可以用立体效应来解释。类似地，硅烷化的 2-吡唑和三唑也在氮处发生了金刚烷化。2-三甲基硅基噻吩、呋喃和吡啶与 1 的反应未能产生位点选择性的单金刚烷化反应。
• Synthesis and Evaluation of the Psychotropic Activity of Framework Derivatives of Alpha-Pyrrolidone
  作者：Yu. N. Klimochkin、I. M. Tkachenko、A. N. Reznikov、V. A. Shiryaev、M. S. Kazachkova、N. S. Kovalev、D. A. Bakulin、E. E. Abrosimova、D. V. Kurkin、I. N. Tyurenkov

  DOI：10.1134/s1068162021060108

  日期：2021.11

  obtained by the reaction of 1-bromadamantane with pyrrolidin-2-one. Homoadamantane-fused pyrrolidin-2-one (TIM-1) was obtained from β-dicarbonyl derivatives of homoadamantane. Synthesis of the starting 2-(5-oxohomoadamantyl)acetic acid was carried out by cleavage of the corresponding keto diester or cyanoketo ester of homoadamantane under the conditions of the Holler–Bauer reaction with sonication

  摘要 α-吡咯烷酮的衍生物和金刚烷的一些衍生物具有广泛的精神活性。进行了α-吡咯烷酮的金刚烷和高金刚烷衍生物的合成及其精神活性的评估。合成了许多在侧链中或作为框架系统一部分含有吡咯烷-2-one 片段的框架化合物。N-(Adamantan-1-yl)pyrrolidin-2-one (TIM-2) 是通过 1-bromadamantane 与 pyrrolidin-2-one 的反应获得的。高金刚烷稠合的 pyrrolidin-2-one (TIM-1) 是从高金刚烷的 β-二羰基衍生物中获得的。起始 2-(5-oxohomoadamantyl) 乙酸的合成是通过在 Holler-Bauer 反应条件下用超声处理裂解相应的高金刚烷酮二酯或氰基酮酯来进行的。然后，将所得的 γ-酮酸引入 Leuckart-Wallach 反应中，得到顺式 -十氢-4,8 :6,10-二甲基环壬烷[ b ]吡咯-2(1
• CYCLOHEXYL SUBSTITUTED PYRROLIDINONES AS INHIBITORS OF 11-BETA-HYDROXYSTEROID DEHYDROGENASE 1
  申请人：Wallace Owen Brendan

  公开号：US20090239911A1

  公开（公告）日：2009-09-24

  The present invention discloses novel compounds of Formula I: having 11β-HSD type 1 antagonist activity, as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula I, as well as methods of using the compounds and compositions to treat diabetes, hyperglycemia, obesity, hypertension, hyperlipidemia, metabolic syndrome, and other conditions associated with 11β-HSD type 1 activity.

  本发明揭示了一种新型的I式化合物，具有11β-HSD type 1拮抗剂活性，以及制备这种化合物的方法。在另一种实施方式中，本发明揭示了包含I式化合物的药物组合物，以及使用这些化合物和组合物治疗糖尿病、高血糖、肥胖症、高血压、高脂血症、代谢综合征和与11β-HSD type 1活性有关的其他疾病的方法。