(1R*,2R*)-2-[(S*)-α-hydroxybenzyl]cyclohexylamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R*,2R*)-2-[(S*)-α-hydroxybenzyl]cyclohexylamine
• 英文别名: 1-(2-aminocyclohexyl)-1-phenylmethanol；2-(phenylhydroxymethyl)cyclohexylamine；(S)-[(1R,2R)-2-aminocyclohexyl]-phenylmethanol
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: OVENHMZWOZRHTP-JHJVBQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R*,2R*)-2-[(S*)-α-hydroxybenzyl]cyclohexylamine 在 sodium hydroxide 、 sodium methylate 作用下， 以 水 、 甲苯 为溶剂， 反应 1.5h， 生成 (4S,4aR,8aR)-4-Phenyl-octahydro-benzo[d][1,3]oxazin-2-one
  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：

  (1R*,2R*)-2-benzoylcyclohexylamine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以70%的产率得到(1R*,2R*)-2-[(S*)-α-hydroxybenzyl]cyclohexylamine
  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 of 5,6-dihydro-4h-1,3-thiazines based on substituted n-phenylthioureas
  作者：B. V. Unkovskii、I. P. Boiko、Yu. F. Malina、T. D. Sokolova、V. F. Shchegel'skii、L. N. Knyaz'kova

  DOI：10.1007/bf00529593

  日期：1992.10
• 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.