(+)-cis-2-(1-pyrrolidinyl)cyclohexylamine | 133575-75-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+)-cis-2-(1-pyrrolidinyl)cyclohexylamine
• 英文别名: (+)-cis-2-(1-pyrolidinyl)cyclohexylamine；cis-2-(1-pyrrolidinyl)cyclohexaneamine；(1S,2R)-2-(Pyrrolidin-1-yl)cyclohexan-1-amine；(1S,2R)-2-pyrrolidin-1-ylcyclohexan-1-amine
• CAS: 133575-75-4
• 化学式: C₁₀H₂₀N₂
• 分子量: 168.282
• InChiKey: FLEFKPPJPOWCSZ-VHSXEESVSA-N

物化性质

• 沸点：
  86 °C(Press: 0.1 Torr)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-cis-2-(1-pyrrolidinyl)cyclohexylamine 生成 (1S,2R)-(+)-cis-2-pyrrolidinyl-N-methylcyclohexylamine
  参考文献：
  名称：

  VONVOIGTLANDER, PHILIP F.;SZMUSZKOVICZ, JACOB

  摘要：

  DOI：
• 作为产物：
  描述：

  trans-2-(N-phenylcarbonylamino)-1-cyclohexanol 在 palladium on activated charcoal 氢氧化钾 、 Jones reagent (CrO₃, conc. H₂SO₄, H₂O) 、 氢气 、 对甲苯磺酸 作用下， 以 乙二醇 、 丙酮 为溶剂， 反应 73.5h， 生成 (+)-cis-2-(1-pyrrolidinyl)cyclohexylamine
  参考文献：
  名称：

  Costa, Brian R. de; Radesca, Lilian, Heterocycles, 1990, vol. 31, # 10, p. 1837 - 1846

  摘要：

  DOI：

文献信息

• [EN] CARBOCYCLIC GLYT1 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES CARBOCYCLIQUES DU RÉCEPTEUR GLYT1
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011023667A1

  公开（公告）日：2011-03-03

  The present invention relates to the use of a compound of general formula (I) wherein R1/R2 are independently from each other hydrogen, lower alkyl, -CH2)o-cycloalkyl for o being 0 or 1, or are benzyl or heterocycloalkyl; or R1 and R2 are together with the N-atom to which they are attached a ring containing -(CH2)3-, -(CH2)4-, -(CH2)5-, -(CH2)2-O-(CH2)2-, -(CH2)2-S-(CH2)2-, -(CH2)2-NR-(CH2)2-, -(CH2)2-C(O)-(CH2)2-, -(CH2)2-CF2-(CH2)2-, -CH2-CHR-(CH2)2, -CHR-(CH2)3, CHR-(CH2)2-CHR-, or is the ring 2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester and R is hydroxy, halogen, cycloalkyl, or C(O)O-lower alkyl; X is -(CH2)4-, -(CH2)3-, -(CH2)2- or -CH2-; R3 is S-lower alkyl, CF3, OCHF2, lower alkoxy, lower alkyl, phenyl, cycloalkyl or halogen; R4 is CF3, lower alkoxy, lower alkyl, halogen and n is 1 or 2; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture, or to its corresponding enantiomers and/or optical isomers thereof for the manufacture of a medicament for the treatment of psychoses, pain, dysfunction in memory and learning, attention deficit, schizophrenia, dementia disorders or Alzheimer's disease.

  本发明涉及一种通式(I)的化合物的使用，其中R1/R2分别独立地为氢、较低的烷基、-CH2)o-环烷基，其中o为0或1，或者为苄基或杂环烷基；或者R1和R2与它们连接的N原子一起形成一个含有-(CH2)3-、-(CH2)4-、-(CH2)5-、-(CH2)2-O-(CH2)2-、-(CH2)2-S-(CH2)2-、-(CH2)2-NR-(CH2)2-、-(CH2)2-C(O)-(CH2)2-、-(CH2)2-CF2-(CH2)2-、-CH2-CHR-(CH2)2、-CHR-(CH2)3、CHR-(CH2)2-CHR-的环，或者是环2,6-二氮杂螺[3.3]庚烷-2-羧酸叔丁基酯，R为羟基、卤素、环烷基或C(O)O-较低烷基；X为-(CH2)4-、-(CH2)3-、-(CH2)2-或-CH2-；R3为S-较低烷基、CF3、OCHF2、较低烷氧基、较低烷基、苯基、环烷基或卤素；R4为CF3、较低烷氧基、较低烷基、卤素，n为1或2；或者用于制备用于治疗精神病、疼痛、记忆和学习功能障碍、注意力缺陷、精神分裂症、痴呆症或阿尔茨海默病的药物的药学上可接受的酸盐、外消旋混合物或其相应的对映体和/或光学异构体。
• CARBOCYCLIC GLYT1 RECEPTOR ANTAGONISTS
  申请人：Kolczewski Sabine

  公开号：US20110053904A1

  公开（公告）日：2011-03-03

  The present invention relates to the use of a compound of formula I wherein R 1 , R 2 , R 3 , R 4 , X and n are as defined herein or to a pharmaceutically acceptable acid addition salt, to a racemic mixture, or to its corresponding enantiomers and/or optical isomers for the treatment of psychoses, pain, dysfunction in memory and learning, attention deficit, schizophrenia, dementia disorders or Alzheimer's disease.

  本发明涉及使用式I的化合物 其中R 1 ，R 2 ，R 3 ，R 4 ，X和n如本文所定义 或其药学上可接受的酸盐，或其相应的对映体和/或光学异构体，用于治疗精神病、疼痛、记忆和学习功能障碍、注意力缺陷、精神分裂症、痴呆症或阿尔茨海默病。
• Cis-N-[(2-aminocycloaliphatic)benzene acetamide and -benzamide anticonvulsants
  申请人：THE UPJOHN COMPANY

  公开号：EP0222533A1

  公开（公告）日：1987-05-20

  Certain cis-N-(2-amino-cycloaliphatic)benzeneacetamide and -benz­amides of the formula where m is 0 or 1, n is 1 or 2, R is hydrogen or alkyl, R₁ and R₂ are separately alkyl, or, taken together with the nitrogen denote a pyrrolidine ring, and X and Y are hydrogen, fluorine, chlorine or bromine or one of X and Y is trifluoromethyl, e.g., cis-3,4-dichloro-­N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzamide and salts thereof, have been found to have CNS seizure blocking or preventing drug action, e.g., anti-convulsant drug properties with little or no analgesic properties. Some of these compounds are new.

  某些顺式-N-(2-氨基环脂族)苯乙酰胺和-苯甲酰胺，其式为 其中m为0或1，n为1或2，R为氢或烷基，R₁和R₂分别为烷基，或与氮一起表示吡咯烷环，X和Y为氢、氟、氯或溴，或X和Y之一为三氟甲基，例如已发现顺式-3,4-二氯-N-甲基-N-[2-(1-吡咯烷基)环己基]苯甲酰胺及其盐类具有中枢神经系统癫痫发作阻断或预防药物作用，例如抗惊厥药物特性，但几乎没有镇痛特性。其中一些化合物是新化合物。
• Synthesis and receptor binding of enantiomeric N-substituted cis-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidinyl)cyclohexylamines as high-affinity .sigma. receptor ligands
  作者：Lilian Radesca、Wayne D. Bowen、Lisa Di Paolo、Brian R. De Costa

  DOI：10.1021/jm00114a015

  日期：1991.10

  N-Alkyl-substituted derivatives of (+)- and (-)-cis-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidinyl)cyclohexylamine have been synthesized in nine steps in a stereospecific manner starting from cyclohexene oxide. The key step in the reaction sequence involved catalytic hydrogenation of oxime 8 in the presence of PtO2 and AcOH to give the cis diamine (+/-)-7. Most of the compounds in this series exhibited very high affinity at sigma-receptors when tested against [H-3]-(+)-3-PPP, and in general it was observed that the 1R,2S enantiomers bound more potently to sigma-receptors than their corresponding 1S,2R enantiomers. The most potent sigma-ligand found in this class was the unsubstituted derivative (1R,2S)-(-)-4, which exhibited an affinity constant of 0.49 nM. This compound was also found to be very selective for sigma-receptors. It exhibited little or no affinity for kappa-opioid, PCP, and dopamine-D2 receptors. It was also demonstrated that the cis configuration as opposed to the trans configuration of (+)- and (-)-5 was necessary for a higher sigma-receptor affinity.
• VONVOIGTLANDER, PHILIP F.;SZMUSZKOVICZ, JACOB
  作者：VONVOIGTLANDER, PHILIP F.、SZMUSZKOVICZ, JACOB

  DOI：——

  日期：——