Ethyl N-acetyl-α-amino-(1-adamantyl)acetate | 100926-39-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl N-acetyl-α-amino-(1-adamantyl)acetate
• 英文别名: ethyl N-acetyl-2-(1-adamantyl)glycinate
• CAS: 100926-39-4
• 化学式: C₁₆H₂₅NO₃
• 分子量: 279.379
• InChiKey: SEPZMMAGVAGSDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  418.6±18.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Ethyl N-acetyl-α-amino-(1-adamantyl)acetate 在 盐酸 、 sodium tetrahydroborate 、 碘 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 30.0h， 生成 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：

  ethyl 2-(adamantan-1-yl)-3-oxobutanoate 在 sodium azide 、 甲烷磺酸 作用下， 以 乙二醇二甲醚 为溶剂， 以70%的产率得到Ethyl N-acetyl-α-amino-(1-adamantyl)acetate
  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

• Amino acids of the adamantane series. I. Synthesis and antiviral activity of α-amino acids of the adamantane series and their derivatives
  作者：P. A. Krasutskii、I. G. Semenova、M. I. Novikova、A. G. Yurchenko、N. A. Leont'eva、T. V. Veselovskaya

  DOI：10.1007/bf00766686

  日期：1985.7
• 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.