cis-N-benzyl-4-phenylcyclohexan-1-amine | 67498-85-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-N-benzyl-4-phenylcyclohexan-1-amine
• 英文别名: cis-Benzyl-4-phenylcyclohexylamin
• CAS: 67498-85-5
• 化学式: C₁₉H₂₃N
• 分子量: 265.398
• InChiKey: VUAXLQTVMNSPPT-KDURUIRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  cis-N-benzyl-4-phenylcyclohexan-1-amine 在 palladium on activated charcoal 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以63%的产率得到cis-4-Phenyl-cyclohexylamin
  参考文献：
  名称：

  Synthesis, GluN2B affinity and selectivity of benzo[7]annulen-7-amines

  摘要：

  Due to their beneficial side effect profile, NMDA receptor antagonists interacting selectively with the allosteric ifenprodil binding site of the GluN2B subunit are of major interest for the treatment of neurological and neurodegenerative disorders. A series of benzo[7]annulen-7-amines 6 was designed by conformational restriction of ifenprodil (1). At first the benzo[7]annulen-7-one 11 was prepared in a three-step synthesis comprising of a double Knoevenagel condensation of phthalaldehyde (7) with dimethyl 3-oxoglutarate (8), hydrogenation of 9 and saponification/decarboxylation of 10. Reductive amination of the ketone 11 with primary amines and NaBH(OAc)(3) led to the secondary amines 6a-d, cis-6h and trans-6i. The tertiary amines 6e-g were obtained by S(N)2-substitution of the nosylate 13. Although H-bond forming substituents in 2- and 5-position are missing, the amines 6 exhibit high affinity towards GluN2B containing NMDA receptors. A distance of four to five bond lengths between the basic amino moiety and the phenyl ring in the side chain appears to be optimal for high GluN2B affinity. The phenylcyclohexylamine cis-6h and the 4-benzylpiperidine 6g show the highest GluN2B affinities (K-i = 2.3 nM and 2.9 nM, respectively). With respect to selectivity against the PCP binding site, sigma(1) and sigma(2) receptors the phenylpiperazine 6f is the most promising GluN2B antagonist. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.10.004
• 作为产物：
  描述：

  4-苯基环己酮 、 苄胺 在 sodium tetrahydroborate 、 2-乙基-己酸稀土盐 作用下， 以 二氯甲烷 为溶剂， 生成 trans-N-benzyl-4-phenylcyclohexan-1-amine 、 cis-N-benzyl-4-phenylcyclohexan-1-amine
  参考文献：
  名称：

  用于立体选择性还原胺化反应的氢化物试剂。改进的3-内-泛醇胺制剂

  摘要：

  用衍生自NaBH 4和各种羧酸的三酰氧基硼氢化钠对取代的环己酮进行还原性胺化反应，可高度非对映选择性地转化为受保护的轴向胺。该方法用于3-内-三聚泛胺的立体选择性制备。

  DOI：

  10.1016/0040-4039(96)00760-5

文献信息

• Cycloalkylurea compounds
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：US05420164A1

  公开（公告）日：1995-05-30

  A cycloalkylurea compound of the formula (I): ##STR1## wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof, which compound inhibits ACAT and is useful as hypolipidemic and antiatherosclerotic medicine.

  一种环状烷基脲化合物，化学式为(I): ##STR1## 其中每个符号如规范中所定义，或其药学上可接受的盐，该化合物抑制ACAT并可用作降脂和抗动脉粥样硬化药物。
• BICYCLIC ARYL AND HETEROARYL COMPOUNDS FOR THE TREATMENT OF METABOLIC DISORDERS
  申请人：Bloxham Jason

  公开号：US20100173886A1

  公开（公告）日：2010-07-08

  Compounds of formula (I): or pharmaceutically acceptable salts thereof, are opioid receptor modulators, e.g. mu-opioid receptor antagonists, neutral antagonists or inverse agonists, and are useful for the treatment of metabolic disorders including obesity.

  化合物式(I)或其药学上可接受的盐，是阿片受体调节剂，例如μ-阿片受体拮抗剂，中性拮抗剂或倒向激动剂，并且可用于治疗代谢性疾病，包括肥胖症。
• Cyclohexylurea compounds
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0507291A1

  公开（公告）日：1992-10-07

  A cycloalkylurea compound of the formula (I): wherein R¹ is a group of the formula (a): (wherein R⁶, R⁷ and R⁸ are the same or different and each is hydrogen or alkyl having 1 to 8 carbon atoms, with the proviso that compounds wherein two or three of R⁶, R⁷ and R⁸ are hydrogens are excluded), haloalkyl, cycloalkyl, alkoxy having 1 to 5 carbon atoms, phenyl, aralkyl or heteroaryl, or phenyl, aralkyl or heteroaryl each substituted on the aromatic ring by 1 to 3 substituents selected from alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 8 carbon atoms, cycloalkyl, cycloalkyloxy, haloalkyl, haloalkoxy, halogen, nitro, amino and substituted amino;    R² is hydrogen, phenyl or phenyl substituted by 1 to 3 substituents selected from alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, haloalkyl and halogen, whererin R¹ and R² may be substituted on the same carbon atom of cycloalkyl ring;    R¹ and R² together may form a substituted or unsubstituted cyclic hydrocarbon having 3 to 7 carbon atoms or a substituted or unsubstituted spiran;    R³ is hydrogen, alkyl having 1 to 8 carbon atoms, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkylthioalkyl, aralkyl substituted by alkylenedioxy, aralkyl, aralkyloxyalkyl, aralkyl or aralkyloxyalkyl each substituted on the aromatic ring by 1 to 3 substituents selected from alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 5 carbon atoms, halogen, nitro, hydroxy, amino, substituted amino, haloalkyl, alkylthio, benzyloxy and benzylthio, heteroarylalkyl, phenoxyalkyl, or heteroarylalkyl or phenoxyalkyl each substituted on the aromatic ring by 1 to 3 substituents selected from halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, nitro, amino and haloalkyl, or a group of the formula (c) or (d): wherein m is 1 or 2, R¹¹ is hydrogen or alkyl having 1 to 4 carbon atoms, R¹² is hydrogen, alkyl having 1 to 4 carbon atoms or aralkyl;    R⁴ is phenyl substituted by 1 to 3 substituents selected from alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, haloalkyl, halogen, amino and substituted amino;    n is 1, 2 or 3; or a pharmaceutically acceptable salt thereof, which compound inhibits ACAT and is useful as hypolipidemic and anti-atherosclerotic medicine.

  式 (I) 的环烷基脲化合物： 其中 R¹ 是式 (a) 的基团： (其中 R⁶、R⁷ 和 R⁸ 相同或不同，且各自为氢或具有 1 至 8 个碳原子的烷基，但 R⁶、R⁷ 和 R⁸ 中的两个或三个为氢的化合物除外）、卤代烷基、环烷基、具有 1 至 5 个碳原子的烷氧基、苯基、芳基或杂芳基，或苯基、芳基或杂芳基、或在芳香环上被 1 至 3 个取代基取代的苯基、芳基或杂芳基，每个取代基均选自 1 至 4 个碳原子的烷基、1 至 8 个碳原子的烷氧基、环烷基、环烷氧基、卤代烷基、卤代烷氧基、卤素、硝基、氨基和取代氨基； R² 是氢、苯基或被 1 至 3 个取代基取代的苯基，这些取代基选自具有 1 至 4 个碳原子的烷基、具有 1 至 4 个碳原子的烷氧基、卤代烷基和卤素，其中 R¹ 和 R² 可在环烷基环的同一碳原子上被取代； R¹ 和 R² 可共同形成具有 3 至 7 个碳原子的取代或未取代的环烃或取代或未取代的螺烷； R³ 是氢、具有 1 至 8 个碳原子的烷基、环烷基、环烷基烷基、烷氧基烷基、烷硫基烷基、被亚烷基二氧基取代的芳基、芳烷基、芳氧基烷基、芳烷基或芳氧基烷基，每个芳环上被 1 至 3 个取代基取代，这些取代基选自具有 1 至 4 个碳原子的烷基、具有 1 至 5 个碳原子的烷氧基、卤素、硝基、羟基、氨基、取代的氨基、烷氧基烷基、烷硫基烷基、被亚烷基二氧基取代的芳烷基、芳氧基烷基、芳氧基烷基、芳氧基烷基或芳氧基烷基、羟基、氨基、取代氨基、卤代烷基、烷硫基、苄氧基和苄硫基、杂芳基烷基、苯氧基烷基、或芳环上各被 1 至 3 个取代基取代的杂芳基烷基或苯氧基烷基，这些取代基选自卤素、具有 1 至 4 个碳原子的烷基、具有 1 至 4 个碳原子的烷氧基、硝基、氨基和卤代烷基或式 (c) 或 (d) 的基团： 其中 m 为 1 或 2，R¹¹ 为氢或具有 1 至 4 个碳原子的烷基，R¹² 为氢、具有 1 至 4 个碳原子的烷基或芳烷基； R⁴ 是被 1 至 3 个取代基取代的苯基，这些取代基选自具有 1 至 4 个碳原子的烷基、具有 1 至 4 个碳原子的烷氧基、卤代烷基、卤素、氨基和取代氨基； n 为 1、2 或 3； 或其药学上可接受的盐、 该化合物可抑制 ACAT，可用作降血脂和抗动脉粥样硬化药物。
• US5420164A
  申请人：——

  公开号：US5420164A

  公开（公告）日：1995-05-30
• US8278442B2
  申请人：——

  公开号：US8278442B2

  公开（公告）日：2012-10-02