2‐((3r,5r,7r)‐adamantan‐1‐yl)‐2‐aminoethan‐1‐ol | 111749-17-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2‐((3r,5r,7r)‐adamantan‐1‐yl)‐2‐aminoethan‐1‐ol
• 英文别名: rac-2-(1-adamantyl)-2-aminoethanol；2-(1-Adamantyl)-2-aminoethanol
• CAS: 111749-17-8
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: HBUUJKSRVMGCEK-UHFFFAOYSA-N

物化性质

• 沸点：
  338.9±15.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  氯甲酸苄酯 、 2‐((3r,5r,7r)‐adamantan‐1‐yl)‐2‐aminoethan‐1‐ol 在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以72%的产率得到rac-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
• 作为产物：
  描述：

  methyl ester of amino-(1-adamantyl)acetic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 2‐((3r,5r,7r)‐adamantan‐1‐yl)‐2‐aminoethan‐1‐ol
  参考文献：
  名称：

  Amino acids of the adamantane series II. Synthesis of adamantyl-containing amino alcohols from α-amino acids and their antiviral activity

  摘要：

  DOI：

  10.1007/bf00758765

文献信息

• KRASUTSKIJ P. A.; SEMENOVA I. G.; NOVIKOVA M. I.; YURCHENKO A. G.; LEONTE+, XIM.-FARMATS. ZH., 21,(1987) N 7, 836-840
  作者：KRASUTSKIJ P. A.、 SEMENOVA I. G.、 NOVIKOVA M. I.、 YURCHENKO A. G.、 LEONTE+

  DOI：——

  日期：——
• [EN] NOVEL COMPOUNDS AS P2X7 MODULATORS AND USES THEREOF<br/>[FR] NOUVEAUX COMPOSES SERVANT DE MODULATEURS DE P2X7 ET LEURS UTILISATIONS
  申请人：RENOVIS INC

  公开号：WO2007028022A2

  公开（公告）日：2007-03-08

  [EN] Compounds are disclosed that have a formula represented by the following (I), the compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, traumatic injury, and others.
  [FR] L'invention concerne des composés de formule (I). Ces composés peuvent être préparés sous forme de composition pharmaceutique et peuvent être utilisés pour prévenir et pour traiter une variété de troubles chez des mammifères, notamment chez les humains, par exemple, de manière non exhaustive, ces troubles peuvent comprendre des douleurs, des inflammations, des lésions traumatiques et autres.
• Amino acids of the adamantane series II. Synthesis of adamantyl-containing amino alcohols from α-amino acids and their antiviral activity
  作者：P. A. Krasutskii、I. G. Semenova、M. I. Novikova、A. G. Yurchenko、N. A. Leont'eva、T. V. Veselovskaya

  DOI：10.1007/bf00758765

  日期：1987.7
• 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.