(1S,2S)-2-methoxy-1-phenylcyclohexylamine | 200800-52-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1S,2S)-2-methoxy-1-phenylcyclohexylamine
• CAS: 200800-52-8
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: SVXCNUJBUUBAKB-STQMWFEESA-N

物化性质

• 沸点：
  302.063±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.040±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  35.25
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-methoxy-1-phenylcyclohexylamine 在 lithium aluminium tetrahydride 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (1S,2S)-2-methoxy-N-methyl-1-phenylcyclohexan-1-amine
  参考文献：
  名称：

  Homochiral ligands derived from cis-1-phenylcyclohexane-1,2-diol and cis-2-azido-2-phenylcyclohexanol

  摘要：

  Homochiral ligands (R,R)-2, (R,R)-3a, (R,R)-3b, (S,S)-4a, and (S,S)-4b were prepared from cis-1-phenylcyclohexane-1,2-diol or cis-2-azido-2-phenylcyclohexanol and were tested as ligands for the nucleophilic addition of alkyllithiums to benzaldehyde 4-anisidineimine. While moderate enantioselectivities (up to 43% e.e.) were observed with (R,R)-3b and (S,S)-4a, (R,R)-2 and (R,R)-3a did not show enantioselectivities. Homochiral secondary amines (S,S)-6a and (S,S)-6b were also prepared from cis-2-azido-2-phenylcyclohexanol. Moderate enantioselectivities (up to 50%) were observed-when they were used as chiral lithium amide base precursors for the deprotonation of 4-t-butylcyclohexanone. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00552-1
• 作为产物：
  描述：

  (S,S)-(+)-1-苯基环己烷-顺-1,2-二醇 在 lithium aluminium tetrahydride 、 sodium azide 、 高氯酸 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 124.5h， 生成 (1S,2S)-2-methoxy-1-phenylcyclohexylamine
  参考文献：
  名称：

  Homochiral ligands derived from cis-1-phenylcyclohexane-1,2-diol and cis-2-azido-2-phenylcyclohexanol

  摘要：

  Homochiral ligands (R,R)-2, (R,R)-3a, (R,R)-3b, (S,S)-4a, and (S,S)-4b were prepared from cis-1-phenylcyclohexane-1,2-diol or cis-2-azido-2-phenylcyclohexanol and were tested as ligands for the nucleophilic addition of alkyllithiums to benzaldehyde 4-anisidineimine. While moderate enantioselectivities (up to 43% e.e.) were observed with (R,R)-3b and (S,S)-4a, (R,R)-2 and (R,R)-3a did not show enantioselectivities. Homochiral secondary amines (S,S)-6a and (S,S)-6b were also prepared from cis-2-azido-2-phenylcyclohexanol. Moderate enantioselectivities (up to 50%) were observed-when they were used as chiral lithium amide base precursors for the deprotonation of 4-t-butylcyclohexanone. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00552-1

文献信息

• Homochiral ligands derived from cis-1-phenylcyclohexane-1,2-diol and cis-2-azido-2-phenylcyclohexanol
  作者：Yoshito Tobe、Hidekazu Iketani、Yuko Tsuchiya、Masayoshi Konishi、Koichiro Naemura

  DOI：10.1016/s0957-4166(97)00552-1

  日期：1997.11

  Homochiral ligands (R,R)-2, (R,R)-3a, (R,R)-3b, (S,S)-4a, and (S,S)-4b were prepared from cis-1-phenylcyclohexane-1,2-diol or cis-2-azido-2-phenylcyclohexanol and were tested as ligands for the nucleophilic addition of alkyllithiums to benzaldehyde 4-anisidineimine. While moderate enantioselectivities (up to 43% e.e.) were observed with (R,R)-3b and (S,S)-4a, (R,R)-2 and (R,R)-3a did not show enantioselectivities. Homochiral secondary amines (S,S)-6a and (S,S)-6b were also prepared from cis-2-azido-2-phenylcyclohexanol. Moderate enantioselectivities (up to 50%) were observed-when they were used as chiral lithium amide base precursors for the deprotonation of 4-t-butylcyclohexanone. (C) 1997 Elsevier Science Ltd.