(cis-2-cyclohexylcyclopentyl)amine | 102677-31-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (cis-2-cyclohexylcyclopentyl)amine
• 英文别名: (1S,2S)-2-cyclohexylcyclopentan-1-amine
• CAS: 102677-31-6
• 化学式: C₁₁H₂₁N
• 分子量: 167.294
• InChiKey: QMVFOIDILDHCDC-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (cis-2-cyclohexylcyclopentyl)amine 在 甲烷磺酸 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 2-<2-<(cis-2-cyclohexylcyclopentyl)imino>-2-phenylethylidene>pyrrolidine
  参考文献：
  名称：

  两种α，α'-二氨基肟的异常酸催化重排†

  摘要：

  2- [2-（烷亚氨基）-2-苯基亚乙基]吡咯烷（vinamidines，3 - 6）中任一获得经由相应vinologous酰胺活化1与米尔文盐以及中间的后续处理2与胺，或更直接地通过苯乙酮的席夫碱与2-乙氧基-1-吡咯啉的酸催化缩合。这些钒胺的亚硝化产生α，α′-二亚氨基肟。在两种情况下（10，11），这些肟经历酸催化的重排形成5,6,7,8-四氢咪唑并[1,2的一个]吡啶环系（12，13）。提供了这些产物之一（13）和一种Viannaidine盐（6）的X射线分析。

  DOI：

  10.1002/hlca.19850680520
• 作为产物：
  描述：

  2-cyclohexylcyclopentanone 在 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 66.0h， 生成 (cis-2-cyclohexylcyclopentyl)amine
  参考文献：
  名称：

  The identification of 7-[(R)-2-((1S,2S)-2-benzyloxycyclopentylamino)-1-hydroxyethyl]-4-hydroxybenzothiazolone as an inhaled long-acting β2-adrenoceptor agonist

  摘要：

  The optimisation of two series of 4-hydroxybenzothiazolone derived β2-adrenoceptor agonists, bearing α-substituted cyclopentyl and β-phenethyl amino-substituents, as inhaled long-acting bronchodilators is described. Analogues were selected for synthesis using a lipophilicity based hypothesis to achieve the targeted rapid onset of action in combination with a long duration of action. The profiling of the two series led to identification of the α-substituted cyclopentyl analogue 2 as the optimal compound with a comparable profile to the inhaled once-daily long-acting β2-adrenoceptor agonist indacaterol. On the basis of these data 2 was promoted as the backup development candidate to indacaterol from the Novartis LABA project.

  DOI：

  10.1016/j.bmcl.2014.06.014

文献信息

• The identification of 7-[(R)-2-((1S,2S)-2-benzyloxycyclopentylamino)-1-hydroxyethyl]-4-hydroxybenzothiazolone as an inhaled long-acting β2-adrenoceptor agonist
  作者：Nicola Arnold、David Beattie、Michelle Bradley、Andrew Brearley、Lyndon Brown、Steven J. Charlton、Robin A. Fairhurst、David Farr、John Fozard、Joe Fullerton、Martin Gosling、Julia Hatto、Diana Janus、Darryl Jones、Lynne Jordan、Christine Lewis、Janet Maas、Clive McCarthy、Mark Mercer、Helen Oakman、Neil Press、Rachel Profit、Friedrich Schuerch、David Sykes、Roger J. Taylor、Alexandre Trifilieff、Andrew Tuffnell

  DOI：10.1016/j.bmcl.2014.06.014

  日期：2014.9

  The optimisation of two series of 4-hydroxybenzothiazolone derived β2-adrenoceptor agonists, bearing α-substituted cyclopentyl and β-phenethyl amino-substituents, as inhaled long-acting bronchodilators is described. Analogues were selected for synthesis using a lipophilicity based hypothesis to achieve the targeted rapid onset of action in combination with a long duration of action. The profiling of the two series led to identification of the α-substituted cyclopentyl analogue 2 as the optimal compound with a comparable profile to the inhaled once-daily long-acting β2-adrenoceptor agonist indacaterol. On the basis of these data 2 was promoted as the backup development candidate to indacaterol from the Novartis LABA project.
• Unusual Acid-Catalyzed Rearrangement of Two ?,??-Diimino-oximes
  作者：Walter Fuhrer、Vittorio Rasetti、Grety Rihs

  DOI：10.1002/hlca.19850680520

  日期：1985.8.14

  and subsequent treatment of the intermediate 2 with an amine, or more directly by acid-catalyzed condensation of the Schiff bases derived from acetophenone with 2-ethoxy-1-pyrroline. Nitrosation of these vinamidines led to α,α′-diimino-oximes. In two cases (10, 11), these oximes underwent acid-catalyzed rearrangement with formation of a 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine ring system (12, 13)

  2- [2-（烷亚氨基）-2-苯基亚乙基]吡咯烷（vinamidines，3 - 6）中任一获得经由相应vinologous酰胺活化1与米尔文盐以及中间的后续处理2与胺，或更直接地通过苯乙酮的席夫碱与2-乙氧基-1-吡咯啉的酸催化缩合。这些钒胺的亚硝化产生α，α′-二亚氨基肟。在两种情况下（10，11），这些肟经历酸催化的重排形成5,6,7,8-四氢咪唑并[1,2的一个]吡啶环系（12，13）。提供了这些产物之一（13）和一种Viannaidine盐（6）的X射线分析。