tert-butyl N-[2-[[(1S,4S,8R)-6-oxo-10-[(1R)-1-phenylethyl]-3,10-diazatricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]amino]ethyl]carbamate | 177723-62-5

• 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: tert-butyl N-[2-[[(1S,4S,8R)-6-oxo-10-[(1R)-1-phenylethyl]-3,10-diazatricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]amino]ethyl]carbamate
• CAS: 177723-62-5
• 化学式: C₂₅H₃₄N₄O₄
• 分子量: 454.569
• InChiKey: SCPGUJZANVFRJH-BVBHFADKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.8
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-[[(1S,4S,8R)-6-oxo-10-[(1R)-1-phenylethyl]-3,10-diazatricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]amino]ethyl]carbamate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 tert-butyl N-[2-[[(1S,4S,8R)-6-oxo-3,10-diazatricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]amino]ethyl]carbamate
  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 palladium on activated charcoal 氢氧化钾 、 sodium hydroxide 、 硼烷四氢呋喃络合物 、 草酰氯 、 甲基锂 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 1-羟基苯并三唑 、 二甲基亚砜 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 环己烯 为溶剂， 反应 19.41h， 生成 tert-butyl N-[2-[[(1S,4S,8R)-6-oxo-10-[(1R)-1-phenylethyl]-3,10-diazatricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]amino]ethyl]carbamate
  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.