1-phenethyl-3-oxo-1-azabicyclo[2.2.1]heptane | 177723-59-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-phenethyl-3-oxo-1-azabicyclo[2.2.1]heptane
• 英文别名: (1S,4R)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]heptan-6-one
• CAS: 177723-59-0
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: BDNQMTPMUBTBHL-WZRBSPASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenethyl-3-oxo-1-azabicyclo[2.2.1]heptane 在 氢氧化钾 、 甲基锂 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.33h， 生成 (2S)-4-oxo-4-[(1S,4R)-6-oxo-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]heptan-5-yl]-2-(phenylmethoxycarbonylamino)butanoic acid
  参考文献：
  名称：

  Design and Asymmetric Synthesis of β-Strand Peptidomimetics

  摘要：

  We describe the asymmetric synthesis of non-peptidic compounds that feature rigid backbone conformations and present various side-chain functions. The key step in the synthesis of these compounds is the C-acylation of an appropriate ketone with a suitably protected aspartic acid derivative. The resulting dipeptide modules may be connected to form tetrapeptide mimics. Specifically is described the mimicry of a four-residue segment of CD4, the cellular receptor of HIV-1. The design was based on molecular modeling and the X-ray crystal structures of CD4 and intended to present the most important-side chains and backbone elements of the Phe43-Lys46 segment.

  DOI：

  10.1021/jo9522771
• 作为产物：
  描述：

  1-phenethyl-1-azabicyclo<2.2.1>-3-heptene 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 草酰氯 、 双氧水 、 二甲基亚砜 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 1-phenethyl-3-oxo-1-azabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Design and Asymmetric Synthesis of β-Strand Peptidomimetics

  摘要：

  We describe the asymmetric synthesis of non-peptidic compounds that feature rigid backbone conformations and present various side-chain functions. The key step in the synthesis of these compounds is the C-acylation of an appropriate ketone with a suitably protected aspartic acid derivative. The resulting dipeptide modules may be connected to form tetrapeptide mimics. Specifically is described the mimicry of a four-residue segment of CD4, the cellular receptor of HIV-1. The design was based on molecular modeling and the X-ray crystal structures of CD4 and intended to present the most important-side chains and backbone elements of the Phe43-Lys46 segment.

  DOI：

  10.1021/jo9522771

文献信息

• Design and Asymmetric Synthesis of β-Strand Peptidomimetics
  作者：Ahcene Boumendjel、John C. Roberts、Essa Hu、Peter V. Pallai、Julius Rebek

  DOI：10.1021/jo9522771

  日期：1996.1.1

  We describe the asymmetric synthesis of non-peptidic compounds that feature rigid backbone conformations and present various side-chain functions. The key step in the synthesis of these compounds is the C-acylation of an appropriate ketone with a suitably protected aspartic acid derivative. The resulting dipeptide modules may be connected to form tetrapeptide mimics. Specifically is described the mimicry of a four-residue segment of CD4, the cellular receptor of HIV-1. The design was based on molecular modeling and the X-ray crystal structures of CD4 and intended to present the most important-side chains and backbone elements of the Phe43-Lys46 segment.