2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline | 95308-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline
• 英文别名: 2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline；2,3,3a,4,5,9b-Hexahydro-1H-cyclopenta[c]chinolin；2,3,3a,4,5,9b-Hexahydro-1H-cyclopenta(c)quinoline；1H-Cyclopenta[c]quinoline, 2,3,3a,4,5,9b-hexahydro-
• CAS: 95308-64-8
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: RECFGDIQHWJCFR-UHFFFAOYSA-N

物化性质

• 沸点：
  283.7±10.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline 在 硫酸 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 水 、 异丙醇 、 甲苯 为溶剂， 反应 7.08h， 生成 2-((3aR,9bS)-2,3,3a,4-tetrahydro-1H-cyclopenta[c]quinolin-5[9bH]-yl)ethanamine hydrochloride
  参考文献：
  名称：

  Imaging Evaluation of 5HT_2C Agonists, [¹¹C]WAY-163909 and [¹¹C]Vabicaserin, Formed by Pictet–Spengler Cyclization

  摘要：

  The serotonin subtype 2C (5HT(2C)) receptor is an emerging and promising drug target to treat several disorders of the human central nervous system. In this current report, two potent and selective 5HT(2C) full agonists, WAY-163909 (2) and vabicaserin (3), were radiolabeled with carbon-11 via Pictet-Spengler cyclization with [C-11]formaldehyde and used in positron emission tomography (PET) imaging. Reaction conditions were optimized to exclude the major source of isotope dilution caused by the previously unknown breakdown of N,N-dimethylformamide (DMF) to formaldehyde at high temperature under mildly acid conditions. In vivo PET imaging was utilized to evaluate the pharmacokinetics and distribution of the carbon-11 labeled 5HT(2C) agonists. Both radiolabeled molecules exhibit high blood-brain barrier (BBB) penetration and nonspecific binding, which was unaltered by preadministration of the unlabeled agonist. Our work demonstrates that Pictet-Spengler cyclization can be used to label drugs with carbon-11 to study their pharmacokinetics and for evaluation as PET radiotracers.

  DOI：

  10.1021/jm401802f
• 作为产物：
  描述：

  N-benzylaniline hydrochloride 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 5.0~20.0 ℃ 、310.27 kPa 条件下， 反应 20.0h， 生成 2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[c]quinoline
  参考文献：
  名称：

  Imaging Evaluation of 5HT_2C Agonists, [¹¹C]WAY-163909 and [¹¹C]Vabicaserin, Formed by Pictet–Spengler Cyclization

  摘要：

  The serotonin subtype 2C (5HT(2C)) receptor is an emerging and promising drug target to treat several disorders of the human central nervous system. In this current report, two potent and selective 5HT(2C) full agonists, WAY-163909 (2) and vabicaserin (3), were radiolabeled with carbon-11 via Pictet-Spengler cyclization with [C-11]formaldehyde and used in positron emission tomography (PET) imaging. Reaction conditions were optimized to exclude the major source of isotope dilution caused by the previously unknown breakdown of N,N-dimethylformamide (DMF) to formaldehyde at high temperature under mildly acid conditions. In vivo PET imaging was utilized to evaluate the pharmacokinetics and distribution of the carbon-11 labeled 5HT(2C) agonists. Both radiolabeled molecules exhibit high blood-brain barrier (BBB) penetration and nonspecific binding, which was unaltered by preadministration of the unlabeled agonist. Our work demonstrates that Pictet-Spengler cyclization can be used to label drugs with carbon-11 to study their pharmacokinetics and for evaluation as PET radiotracers.

  DOI：

  10.1021/jm401802f

文献信息

• Aerobic oxidative dehydrogenation of N-heterocycles over OMS-2-based nanocomposite catalysts: preparation, characterization and kinetic study
  作者：Xiuru Bi、Tao Tang、Xu Meng、Mingxia Gou、Xiang Liu、Peiqing Zhao

  DOI：10.1039/c9cy01968e

  日期：——

  aerobic oxidative dehydrogenation of N-heterocycles were examined in detail. Many tetrahydroquinoline derivatives and a broad range of other N-heterocycles could be tolerated by the catalytic system using a biomass-derived solvent as a reaction medium. Newly generated mixed crystal phases, noticeably enhanced surface areas and labile lattice oxygen of the OMS-2-based nanocomposite catalysts might contribute

  首次制备了掺有钨的基于OMS-2的纳米复合材料，并详细研究了它们在N杂环的好氧氧化脱氢中的显着增强的催化活性和可回收性。使用生物质衍生的溶剂作为反应介质的催化体系可以耐受许多四氢喹啉衍生物和各种其他N-杂环。OMS-2基纳米复合催化剂的新生成的混合晶体相，显着增加的表面积和不稳定的晶格氧可能有助于其出色的催化性能。此外，进行了广泛的动力学研究，得出的结论是1,2,3,4-四氢喹啉的脱氢是一级反应，表观活化能为29.66 kJ mol -1。
• A simple route to C-functionalised azaxylylenes and diazaxylylenes
  作者：Colin W. G. Fishwick、Richard C. Storr、Paul W. Manley

  DOI：10.1039/c39840001304

  日期：——

  o-Lithiation of t-butoxycarbonylaniline and 4-t-butoxycarbonylaminopyridine followed by reaction with aldehydes gives t-butoxycarbonylamino alcohols which are converted into azaxylylenes and diazaxylylenes on flash pyrolysis.

  叔丁氧羰基苯胺和4-叔丁氧羰基氨基吡啶的邻位锂化，然后与醛反应，得到叔丁氧羰基氨基醇，在快速热解中将其转化成氮杂亚烷基和二氮杂亚烷基。
• MnOx/catechol/H2O: A cooperative catalytic system for aerobic oxidative dehydrogenation of N-heterocycles at room temperature
  作者：Tao Tang、Xiuru Bi、Xu Meng、Gexin Chen、Mingxia Gou、Xiang Liu、Peiqing Zhao

  DOI：10.1016/j.tetlet.2019.151425

  日期：2020.1

  Amorphous manganese oxide doped by Na+ ion (Na-AMO) was successfully prepared and found to be an efficient heterogeneous catalyst in aerobic oxidative dehydrogenation of N-heterocycles, cooperate with catachol. Na-AMO was fully characterized by XRD, XPS BET H2-TPR, CO2-TPD FT-IR, TEM, SEM and had rich amounts of surface absorbed active oxygen species which are responsible for superior catalytic performance

  成功制备了Na +离子掺杂的无定形锰氧化物（Na-AMO），发现它是N-杂环好氧氧化脱氢的有效多相催化剂，与催化裂化反应配合使用。Na-AMO通过XRD，XPS BET H 2 -TPR，CO 2 -TPD FT-IR，TEM，SEM进行了全面表征，并具有大量的表面吸收活性氧，这些都具有优异的催化性能。Na-AMO和邻苯二酚之间的协同相互作用使催化系统高效且具有耐受性，在温和条件下，该系统可提供各种N-杂环化合物，收率好至极佳。
• Diazepinoquinolines, synthesis thereof, and intermediates thereto
  申请人：Megati Sreenivasulu

  公开号：US20070027142A1

  公开（公告）日：2007-02-01

  The present invention relates to methods for synthesizing compounds useful as 5HT 2C agonists or partial agonists, derivatives thereof, and to intermediates thereto.

  本发明涉及用作5HT2C激动剂或部分激动剂的化合物的合成方法，以及其衍生物和中间体。
• HETEROCYCLIC-SUBSTITUTED PIPERIDINE COMPOUNDS AND THE USES THEREOF
  申请人：Brown Kevin C.

  公开号：US20100022519A1

  公开（公告）日：2010-01-28

  The invention relates to Heterocyclic-Substituted Piperidine Compounds, compositions comprising an effective amount of a Heterocyclic-Substituted Piperidine Compound and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of a Heterocyclic-Substituted Piperidine Compound.

  本发明涉及杂环取代哌啶化合物，包括含有有效量的杂环取代哌啶化合物的组合物和治疗或预防疾病的方法，例如疼痛，通过向需要治疗的动物施用有效量的杂环取代哌啶化合物。