{2-[(E)-Benzylimino]-cyclohexyl}-phenyl-methanone | 350029-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {2-[(E)-Benzylimino]-cyclohexyl}-phenyl-methanone
• 英文别名: (2-Benzyliminocyclohexyl)-phenylmethanone
• CAS: 350029-02-6
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: OSZLFPYOGNOYNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  {2-[(E)-Benzylimino]-cyclohexyl}-phenyl-methanone 在 platinum on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、6.0 MPa 条件下， 反应 144.0h， 以91%的产率得到(S)-((1R,2S)-2-Benzylamino-cyclohexyl)-phenyl-methanol
  参考文献：
  名称：

  Synthesis and transformations of 2-(phenylhydroxymethyl)cyclohexylamines

  摘要：

  Diastereomeric 2-(phenylhydroxymethyl)cyclohexylamines were synthesised by reduction of 2-benzoylcyclohexylamines. (1S*,2R*)-2-Benzoylcyclohexylamine can be reduced diastereoselectively to the corresponding gamma -amino alcohol with sodium borohydride; for the trans counterpart (1R*,2R*)-2-benzoylcyclohexylamine, lithium aluminium hydride was found to be a selective reducing agent. In both cases, high syn selectivities were observed. The amino alcohols were transformed to the corresponding cyclohexane-fused tetrahydro-1,3-oxazin-2-ones and -2-thiones. The gamma -amino alcohols reacted with arylimidates to afford 4,5-dihydro-6H-1,3-oxazines. Their cyclization with phenyl isothiocyanate yielded 2-phenyliminotetrahydro-1,3-oxazines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00176-4
• 作为产物：
  描述：

  苄胺 、 2-苯甲酰环己酮 以 甲苯 为溶剂， 反应 3.0h， 以78%的产率得到{2-[(E)-Benzylimino]-cyclohexyl}-phenyl-methanone
  参考文献：
  名称：

  Synthesis and transformations of 2-(phenylhydroxymethyl)cyclohexylamines

  摘要：

  Diastereomeric 2-(phenylhydroxymethyl)cyclohexylamines were synthesised by reduction of 2-benzoylcyclohexylamines. (1S*,2R*)-2-Benzoylcyclohexylamine can be reduced diastereoselectively to the corresponding gamma -amino alcohol with sodium borohydride; for the trans counterpart (1R*,2R*)-2-benzoylcyclohexylamine, lithium aluminium hydride was found to be a selective reducing agent. In both cases, high syn selectivities were observed. The amino alcohols were transformed to the corresponding cyclohexane-fused tetrahydro-1,3-oxazin-2-ones and -2-thiones. The gamma -amino alcohols reacted with arylimidates to afford 4,5-dihydro-6H-1,3-oxazines. Their cyclization with phenyl isothiocyanate yielded 2-phenyliminotetrahydro-1,3-oxazines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00176-4

文献信息

• Synthesis and transformations of 2-(phenylhydroxymethyl)cyclohexylamines
  作者：Péter Csomós、Gábor Bernáth、Pál Sohár、Antal Csámpai、Norbert De Kimpe、Ferenc Fülöp

  DOI：10.1016/s0040-4020(01)00176-4

  日期：2001.4

  Diastereomeric 2-(phenylhydroxymethyl)cyclohexylamines were synthesised by reduction of 2-benzoylcyclohexylamines. (1S*,2R*)-2-Benzoylcyclohexylamine can be reduced diastereoselectively to the corresponding gamma -amino alcohol with sodium borohydride; for the trans counterpart (1R*,2R*)-2-benzoylcyclohexylamine, lithium aluminium hydride was found to be a selective reducing agent. In both cases, high syn selectivities were observed. The amino alcohols were transformed to the corresponding cyclohexane-fused tetrahydro-1,3-oxazin-2-ones and -2-thiones. The gamma -amino alcohols reacted with arylimidates to afford 4,5-dihydro-6H-1,3-oxazines. Their cyclization with phenyl isothiocyanate yielded 2-phenyliminotetrahydro-1,3-oxazines. (C) 2001 Elsevier Science Ltd. All rights reserved.