2-(pyrrolidin-1-yl)cyclohexanone | 118207-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-(pyrrolidin-1-yl)cyclohexanone
• 英文别名: 2-(1-pyrrolidinyl)cyclohexanone；2-pyrrolidin-1-ylcyclohexan-1-one
• CAS: 118207-34-4
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: LWXDJEHVWVQRLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(pyrrolidin-1-yl)cyclohexanone 在 RuCl₂[(S)-SDP][(R,R)-DPEN] potassium tert-butylate 、 氢气 作用下， 以 异丙醇 为溶剂， 18.0~25.0 ℃ 、1.01 MPa 条件下， 反应 2.0h， 以90%的产率得到(1S,2R)-2-(pyrrolidin-1-yl)cyclohexanol
  参考文献：
  名称：

  动态动力学拆分允许通过钌催化的不对称氢化高度对映选择性地合成顺式-α-氨基环烷醇。

  摘要：

  DOI：

  10.1002/anie.200702491
• 作为产物：
  描述：

  2-(pyrrolidin-1-yl)cyclohexanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 2-(pyrrolidin-1-yl)cyclohexanone
  参考文献：
  名称：

  不同胺碱在β-氨基醇的Swern氧化中的作用

  摘要：

  含有叔氨基的β-氨基醇的剧烈氧化得到相应的α-氨基羰基化合物，收率相当好。产率取决于用于反应的胺碱的空间要求，并且取决于β-氨基醇底物，通过使用N-甲基吡咯烷，N-乙基哌啶或三乙胺来优化产率。

  DOI：

  10.1016/s0040-4039(97)00283-9

文献信息

• The Rabe amination after a century: direct addition of N-heterocycles to carbonyl compounds
  作者：Daniele M. Scarpino Schietroma、Mattia R. Monaco、Valerio Bucalossi、Philipp E. Walter、Patrizia Gentili、Marco Bella

  DOI：10.1039/c2ob25595b

  日期：——

  presented. This kind of reaction was originally employed in 1918 in a key step for the conversion of quinotoxine to quinine. Ketones and α-substituted aldehydes give the corresponding α-aminated carbonyl compounds in moderate yield. α,α-Unsubstituted aldehydes give rise to amino ketones via a novel rearrangement.

  提出了Rabe亲电子胺化的催化形式。这种反应最初是在1918年采用的，是转化为喹诺酮 到 奎宁。酮和α-取代的醛以中等收率得到相应的α-胺化的羰基化合物。α，α-未取代的醛通过新颖的重排生成氨基酮。
• The effect of different amine bases in the Swern oxidation of β-amino alcohols
  作者：William Chrisman、Bakthan Singaram

  DOI：10.1016/s0040-4039(97)00283-9

  日期：1997.3

  Swern oxidation of β-amino alcohols containing tertiary amino groups afforded the corresponding α-amino carbonyl compounds in fair to excellent yield. Yields were dependent on the steric requirement of the amine base used for the reaction and were optimized by the use of N-methylpyrrolidine, N-ethylpiperidine, or triethylamine, depending on the β-amino alcohol substrate.

  含有叔氨基的β-氨基醇的剧烈氧化得到相应的α-氨基羰基化合物，收率相当好。产率取决于用于反应的胺碱的空间要求，并且取决于β-氨基醇底物，通过使用N-甲基吡咯烷，N-乙基哌啶或三乙胺来优化产率。
• Nitrogen-containing cyclohetero cycloalkylaminoaryl derivatives for CNS
  申请人：The United States of America as represented by the Department of Health

  公开号：US05739158A1

  公开（公告）日：1998-04-14

  Certain nitrogen-containing cyclohetero cycloalkylaminoaryl compounds are described for treatment of CNS disorders such as cerebral ischemia, psychotic disorders, convulsions and parkinsonism. Compounds of particular interest are of the formula ##STR1## wherein R.sup.1 is selected from hydrido, loweralkyl, cycloalkylalkyl of four to six carbon atoms and loweralkenylloweralkyl; wherein each of R.sup.2 and R.sup.3 is independently selected from hydrido and loweralkyl; wherein each of R.sup.4 through R.sup.7, R.sup.10 and R.sup.11 is independently selected from hydrido, hydroxy, loweralkyl, benzyl, phenoxy, benzyloxy and haloloweralkyl; wherein n is a number selected from four through six; wherein p is a number selected from zero through four; wherein q is a number selected from three through five; wherein A is selected from phenyl, naphthyl and thienyl; wherein any of the foregoing A groups can be further substituted with one or more substituents independently selected from hydrido, hydroxy, loweralkyl, loweralkoxy, halo, haloloweralkyl, amino, monoloweralkylamino and diloweralkylamino; or a pharmaceutically acceptable salt thereof.

  描述了用于治疗中枢神经系统疾病，如脑缺血、精神病性障碍、惊厥和帕金森症的某些含氮环杂环烷基氨基芳基化合物。特别感兴趣的化合物具有以下结构：其中R.sup.1从氢代基、低碳原子数的环烷基烷基和低碳烯基烷基中选择；其中R.sup.2和R.sup.3分别独立地从氢代基和低碳烷基中选择；其中R.sup.4至R.sup.7、R.sup.10和R.sup.11分别独立地从氢代基、羟基、低碳烷基、苄基、苯氧基、苄氧基和卤代低碳烷基中选择；其中n是从四到六中选择的数字；其中p是从零到四中选择的数字；其中q是从三到五中选择的数字；其中A从苯基、萘基和噻吩基中选择；其中上述任何A基都可以进一步取代一个或多个取代基，这些取代基独立地从氢代基、羟基、低碳烷基、低碳氧基、卤代基、卤代低碳烷基、氨基、单低碳烷基氨基和双低碳烷基氨基中选择；或其药用盐。
• Efficient preparation of cis vicinal tertiary diamines from 2-hydroxy ketones in two steps
  作者：Gideon Fraenkel、Judith Gallucci、Howard S. Rosenzweig

  DOI：10.1021/jo00264a031

  日期：1989.2
• 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.