cis-4-(benzylamino)cyclohexanol

• 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-4-(benzylamino)cyclohexanol
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: QPRIOPMWGXBPOQ-BETUJISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  32.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  苯甲羟肟酸 在 palladium on activated charcoal aluminum amalgam 、 lithium aluminium tetrahydride 、 tetramethylammonium metaperiodate 、 水 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 40.0h， 生成 cis-4-(benzylamino)cyclohexanol
  参考文献：
  名称：

  Synthetic approaches to nortropanes and nortrop-6-enes; intramolecular displacement by nitrogen in 7-membered rings

  摘要：

  The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described. The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described. Nitrogen inversion data for selected nortropane derivatives are included.

  DOI：

  10.1016/s0040-4020(01)80313-6

文献信息

• A rapid and practical entry into cis-1,4-aminocyclohexanols
  作者：Fabrice Gallou、Bo Han、Jiang Lu、Manuela Seeger-Weibel、Anne-Florence Stoessel、Simon Allmendinger

  DOI：10.1016/j.tetlet.2010.01.029

  日期：2010.3

  A selective and practical approach for the formation of cis-1,4-aminocyclohexanol was developed. The key transformation involves a one-pot imine formation/ Lewis acid-directed imine reduction and results in a highly selective attack of the reducing agent. This simple and practical method is easily amenable to large-scale synthesis. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthetic approaches to nortropanes and nortrop-6-enes; intramolecular displacement by nitrogen in 7-membered rings
  作者：Antoinette Naylor (nee Bathgate)、Nicola Howarth、John R. Malpass

  DOI：10.1016/s0040-4020(01)80313-6

  日期：1993.1

  The synthesis of simple nortropane and nortrop-6-ene derivatives from cyclohepta-1,3-diene is described. The key intermediates are trans-1-amino-4-chloro-cycloheptanes and -cyclohept-2-enes which are derived efficiently from the corresponding cis-amino-alcohols and undergo intramolecular cyclisation. Corresponding derivatisation of cyclohexa- and cycloocta-1,3-dienes is explored and attempts to achieve Pd-catalysed cyclisation of 1-amino-4-acetoxy-derivatives is described. Nitrogen inversion data for selected nortropane derivatives are included.