1-(1,4-二氧杂-8-氮杂螺[4.5]癸-8-基)乙酮 | 176910-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 中文名称: 1-(1,4-二氧杂-8-氮杂螺[4.5]癸-8-基)乙酮
• 中文别名: 5,5,12,12-四丁基-7,10-二羰基-6,11-二氧杂-5,12-二锡杂十六碳-8-烯
• 英文名称: 1-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)ethanone
• 英文别名: 1-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethanone
• CAS: 176910-35-3
• 化学式: C₉H₁₅NO₃
• mdl: MFCD01474465
• 分子量: 185.223
• InChiKey: JCOXNZIRVHDDAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1,4-二氧杂-8-氮杂螺[4.5]癸-8-基)乙酮 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 30.0h， 生成 N-乙基-4-哌啶酮
  参考文献：
  名称：

  Eclipsed Conformation of the Exocyclic N−CH₂ Bond in N-Neopentylpiperidines and the Stereodynamic Consequences As Studied by Dynamic NMR Spectroscopy and Molecular Mechanics Calculations

  摘要：

  The dynamic stereochemistry of a range of N-neopentylpiperidines 1 with an eclipsed N-CH2-t-Bu bond is compared with that of the corresponding range of N-ethylpiperidines 2 with a gauche N-CH2Me bond. By using dynamic NMR spectroscopy, the relative importance of ring inversion, exocyclic bond rotation, and nitrogen inversion are elucidated and barriers are reported and discussed. Minor populations of the neopentyl-axial-eclipsed conformation are detected directly and identified with the help of molecular mechanics calculations. The corresponding N-alkylpyrrolidines are also reported.

  DOI：

  10.1021/jo9720344
• 作为产物：
  描述：

  乙酸酐 、 4-哌啶酮缩乙二醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到1-(1,4-二氧杂-8-氮杂螺[4.5]癸-8-基)乙酮
  参考文献：
  名称：

  Antinociceptive Effects of 1-Acyl-4-dialkylaminopiperidine and 1-Alkyl-4-dialkylaminopiperidine in Mice: Structure-Activity Relation Study of Matrine-Type Alkaloids.

  摘要：

  我们以前曾报道过(+)-matrine和(+)-allomatrine具有主要通过激活κ-阿片受体介导的抗痛觉特性。研究人员合成了1-酰基-4-二烷基氨基哌啶类化合物作为马曲林的最简单衍生物，并通过醋酸诱导的腹部收缩试验研究了其结构与活性的关系。结果表明，1-烷基-4-二烷基氨基哌啶的抗痛觉效力明显低于相应的 1-酰基-4-二烷基氨基哌啶。这些发现表明，(+)-马曲林的酰胺基是影响抗痛觉效力的一个重要官能团。

  DOI：

  10.1248/bpb.25.1030

文献信息

• Mild and chemoselective catalytic deprotection of ketals and acetals using cerium(IV) ammonium nitrate
  作者：Ali Ates、Arnaud Gautier、Bernard Leroy、Jean-Marc Plancher、Yannick Quesnel、Jean-Christophe Vanherck、István E Markó

  DOI：10.1016/j.tet.2003.03.002

  日期：2003.11

  Cerium(IV) ammonium nitrate (CAN) is a powerful, though mild, reagent for the efficient and selective removal of a range of ketals and acetals. This novel deprotection method requires only catalytic amounts of CAN and tolerates a variety of functional and protecting groups. Mechanistic insights suggest that the Ce(IV) salts act as unique Lewis acids and not as redox active species.

  硝酸铈（IV）铵（CAN）是一种功能强大的试剂，尽管温和，但可以有效，选择性地去除一系列缩酮和乙缩醛。这种新颖的脱保护方法仅需要催化量的CAN，并能耐受各种功能和保护基团。机械学的见解表明，Ce（IV）盐起独特的路易斯酸的作用，而不是氧化还原活性物质。
• Remarkably efficient deprotection of cyclic acetals and ketals
  作者：Ali Ates、Arnaud Gautier、Bernard Leroy、Jean-Marc Plancher、Yannick Quesnel、István E Markó

  DOI：10.1016/s0040-4039(99)00013-1

  日期：1999.2

  A simple and mild procedure for the efficient deprotection of cyclic acetals and ketals, using cerium ammonium nitrate (CAN) is reported. The method tolerates a range of functional and protecting groups and is suitable for acid-labile substrates.

  据报道，使用硝酸铈铵（CAN）可以简单，温和地有效去除环缩醛和缩酮。该方法可耐受一定范围的官能团和保护基，适用于酸不稳定的底物。
• [EN] NOVEL FXR (NR1H4) MODULATING COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS MODULANT FXR (NR1H4)
  申请人：GILEAD SCIENCES INC

  公开号：WO2016096116A1

  公开（公告）日：2016-06-23

  The present invention relates to compounds which bind to the NR1 H4 receptor (FXR) and act as agonists of FXR. The invention further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of said nuclear receptor by said compounds and to a process for the synthesis of said compounds.

  本发明涉及结合NR1 H4受体（FXR）并作为FXR激动剂的化合物。该发明还涉及利用这些化合物制备药物以治疗疾病和/或症状，通过这些化合物结合所述核受体来实现，并涉及这些化合物的合成过程。
• Benzimidazole and Pyridylimidazole Derivatives
  申请人：Li Guiying

  公开号：US20080227793A1

  公开（公告）日：2008-09-18

  This invention relates to benzimidazoles, pyridylimidazoles and related bicyclic heteroaryl compounds, all of which may be described by of Formula I The invention is particularly related to such compounds that bind with high selectivity and high affinity to the benzodiazepine site of GABA A receptors. This invention also relates to pharmaceutical compositions comprising such compounds and to the use of such compounds in treatment of certain central nervous system (CNS) diseases. Novel processes for preparing compounds of Formula I are disclosed. This invention also relates to the use of benzimidazoles, pyridylimidazoles and related bicyclic heteroaryl compounds of Formula I in combination with one or more other CNS agents to potentiate the effects of the other CNS agents. Additionally this invention relates to the use such compounds as probes for the localization of GABA A receptors in tissue sections.

  本发明涉及苯并咪唑、吡啶咪唑和相关的双环杂芳烃化合物，所有这些化合物都可以用公式I描述。本发明特别涉及与GABAA受体的苯二氮卓位点具有高选择性和高亲和力的这种化合物。本发明还涉及包含这种化合物的制药组合物以及在治疗某些中枢神经系统（CNS）疾病中使用这种化合物的用途。还公开了制备公式I化合物的新方法。本发明还涉及将公式I的苯并咪唑、吡啶咪唑和相关的双环杂芳烃化合物与一个或多个其他CNS药剂联合使用以增强其他CNS药剂的效果。此外，本发明还涉及将这些化合物用作定位组织切片中的GABAA受体的探针。
• Novel FXR (NR1H4) modulating compounds
  申请人：Gilead Sciences, Inc.

  公开号：EP3034499A1

  公开（公告）日：2016-06-22

  The present invention relates to compounds of formula (1) which bind to the NR1H4 receptor (FXR) and act as agonists of FXR. The invention further relates to the use of the compounds for the preparation of a medicament for the treatment of diseases and/or conditions through binding of said nuclear receptor by said compounds and to a process for the synthesis of said compounds.

  本发明涉及与 NR1H4 受体 (FXR) 结合并作为 FXR 激动剂的式 (1) 化合物。本发明进一步涉及化合物在制备通过所述化合物与所述核受体结合治疗疾病和/或病症的药物中的用途，以及所述化合物的合成工艺。