(3aR,7aR)-1,3-bis[(1S)-1-phenylethyl]-2,3,3a,4,7,7a-hexahydro-1H-benzimidazole | 1253965-66-0

• 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: (3aR,7aR)-1,3-bis[(1S)-1-phenylethyl]-2,3,3a,4,7,7a-hexahydro-1H-benzimidazole
• 英文别名: (3aR,7aR)-1,3-bis[(1S)-1-phenylethyl]-3a,4,7,7a-tetrahydro-2H-benzimidazole
• CAS: 1253965-66-0
• 化学式: C₂₃H₂₈N₂
• 分子量: 332.489
• InChiKey: IFYHKPRUTQEVPT-BZRIBIQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aR,7aR)-1,3-bis[(1S)-1-phenylethyl]-2,3,3a,4,7,7a-hexahydro-1H-benzimidazole 在 dimethyl sulfide borane 、 水 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以20%的产率得到(3aR,7aR)-1,3-bis((S)-1-phenylethyl)octahydro-1H-benzo[d]imidazole
  参考文献：
  名称：

  Asymmetric Synthesis of 3,4-Diaminocyclohexanol and endo-7-Azabicyclo[2.2.1]heptan-2-amine

  摘要：

  Hydroboration of (1R,2R)-bis[(S)-1-phenylethylamino]cyclohex-4-ene and its derivatives with several borane reagents gave diastereomeric mixtures of the 3,4-diaminocyclohexanol derivatives. Cyclization of the prevalent diastereomer with the R configuration of the newly formed stereocenter under Mitsunobu conditions, followed by reductive removal of the N-substituents, gave the optically pure endo-7-azabicyclo[2.2.1]heptane-2-amine.

  DOI：

  10.1021/ol102103y
• 作为产物：
  描述：

  聚合甲醛 、 (1R,2R,1'S,1''S)-N,N'-di(α-phenylethyl)-4-cyclohexene-1,2-diamine 在 magnesium sulfate 、 对甲苯磺酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以98%的产率得到(3aR,7aR)-1,3-bis[(1S)-1-phenylethyl]-2,3,3a,4,7,7a-hexahydro-1H-benzimidazole
  参考文献：
  名称：

  Asymmetric Synthesis of 3,4-Diaminocyclohexanol and endo-7-Azabicyclo[2.2.1]heptan-2-amine

  摘要：

  Hydroboration of (1R,2R)-bis[(S)-1-phenylethylamino]cyclohex-4-ene and its derivatives with several borane reagents gave diastereomeric mixtures of the 3,4-diaminocyclohexanol derivatives. Cyclization of the prevalent diastereomer with the R configuration of the newly formed stereocenter under Mitsunobu conditions, followed by reductive removal of the N-substituents, gave the optically pure endo-7-azabicyclo[2.2.1]heptane-2-amine.

  DOI：

  10.1021/ol102103y

文献信息

• Asymmetric Synthesis of 3,4-Diaminocyclohexanol and <i>endo</i>-7-Azabicyclo[2.2.1]heptan-2-amine
  作者：Diego Savoia、Stefano Grilli、Andrea Gualandi

  DOI：10.1021/ol102103y

  日期：2010.11.5

  Hydroboration of (1R,2R)-bis[(S)-1-phenylethylamino]cyclohex-4-ene and its derivatives with several borane reagents gave diastereomeric mixtures of the 3,4-diaminocyclohexanol derivatives. Cyclization of the prevalent diastereomer with the R configuration of the newly formed stereocenter under Mitsunobu conditions, followed by reductive removal of the N-substituents, gave the optically pure endo-7-azabicyclo[2.2.1]heptane-2-amine.