tert-butyl N-[2-[[(1S,4S,8R)-10-[(2R,8S)-8-benzyl-4-oxo-2,3,5,6,7,8-hexahydro-1H-quinoline-2-carbonyl]-6-oxo-3,10-diazatricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]amino]ethyl]carbamate | 177723-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: tert-butyl N-[2-[[(1S,4S,8R)-10-[(2R,8S)-8-benzyl-4-oxo-2,3,5,6,7,8-hexahydro-1H-quinoline-2-carbonyl]-6-oxo-3,10-diazatricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]amino]ethyl]carbamate
• CAS: 177723-63-6
• 化学式: C₃₄H₄₃N₅O₆
• 分子量: 617.745
• InChiKey: MMZODLCFGJMRMR-SSXAXAPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-[[(1S,4S,8R)-10-[(2R,8S)-8-benzyl-4-oxo-2,3,5,6,7,8-hexahydro-1H-quinoline-2-carbonyl]-6-oxo-3,10-diazatricyclo[6.2.1.02,7]undec-2(7)-ene-4-carbonyl]amino]ethyl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以51%的产率得到(1S,4S,8R)-N-(2-aminoethyl)-10-[(2R,8S)-8-benzyl-4-oxo-2,3,5,6,7,8-hexahydro-1H-quinoline-2-carbonyl]-6-oxo-3,10-diazatricyclo[6.2.1.02,7]undec-2(7)-ene-4-carboxamide
  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 、 氢气 、 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， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 67.41h， 生成 tert-butyl N-[2-[[(1S,4S,8R)-10-[(2R,8S)-8-benzyl-4-oxo-2,3,5,6,7,8-hexahydro-1H-quinoline-2-carbonyl]-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

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.