(S)-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol | 328969-77-3

• 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: (S)-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol
• 英文别名: benzyl N-[(1R)-1-(1-adamantyl)-2-hydroxyethyl]carbamate
• CAS: 328969-77-3
• 化学式: C₂₀H₂₇NO₃
• 分子量: 329.439
• InChiKey: AHXKIJOIOXCFPA-AZRLCKCBSA-N

物化性质

• 沸点：
  503.0±43.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以56%的产率得到(R)-N-(benzyloxycarbonyl)-2-(1-adamantyl)glycine
  参考文献：
  名称：

  Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: a combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution

  摘要：

  Alkylation of the cobalt(II) complex of ethyl acetoacetate with 1-bromoadamantane affords ethyl 2-(1-adamantyl)acetoacetate, which was converted into rac-(1-adamantyl)glycine 1 and rac-2-(1-adamantyl)-2-aminoethanol 7. This was separated into enantiomers by means of vinyl acetate in the presence of Pseudomonas cepacea. Configuration R was assigned to the enantiomerically pure aminoalcohol (R)-7 on the basis of X-ray diffraction data. Further oxidation of N-protected aminoalcohol (R)-8 afforded enantiomerically pure amino acid (R)-1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00428-6
• 作为产物：
  描述：

  乙酸乙烯酯 、 rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 在 Pseudomonas cepacia lipase 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 以82%的产率得到(S)-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol
  参考文献：
  名称：

  Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: a combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution

  摘要：

  Alkylation of the cobalt(II) complex of ethyl acetoacetate with 1-bromoadamantane affords ethyl 2-(1-adamantyl)acetoacetate, which was converted into rac-(1-adamantyl)glycine 1 and rac-2-(1-adamantyl)-2-aminoethanol 7. This was separated into enantiomers by means of vinyl acetate in the presence of Pseudomonas cepacea. Configuration R was assigned to the enantiomerically pure aminoalcohol (R)-7 on the basis of X-ray diffraction data. Further oxidation of N-protected aminoalcohol (R)-8 afforded enantiomerically pure amino acid (R)-1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00428-6

文献信息

• Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: a combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution
  作者：Jaume Clariana、Santiago Garcı́a-Granda、Vicente Gotor、Angel Gutiérrez-Fernández、Amparo Luna、Marcial Moreno-Mañas*、Adelina Vallribera

  DOI：10.1016/s0957-4166(00)00428-6

  日期：2000.11

  Alkylation of the cobalt(II) complex of ethyl acetoacetate with 1-bromoadamantane affords ethyl 2-(1-adamantyl)acetoacetate, which was converted into rac-(1-adamantyl)glycine 1 and rac-2-(1-adamantyl)-2-aminoethanol 7. This was separated into enantiomers by means of vinyl acetate in the presence of Pseudomonas cepacea. Configuration R was assigned to the enantiomerically pure aminoalcohol (R)-7 on the basis of X-ray diffraction data. Further oxidation of N-protected aminoalcohol (R)-8 afforded enantiomerically pure amino acid (R)-1. (C) 2000 Elsevier Science Ltd. All rights reserved.