verrucine A

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: verrucine A
• 英文别名: syn-1,3,4,6-tetrahydro-3,6-dioxo-1-(phenylmethyl)-2H-pyrazino[2,1-b]quinazoline-4-propanamide；3-(1-benzyl-3,6-dioxo-2,4-dihydro-1H-pyrazino[2,1-b]quinazolin-4-yl)propanamide
• 化学式: C₂₁H₂₀N₄O₃
• 分子量: 376.415
• InChiKey: LISCNUCDEMJKLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[(1S)-2-氯-2-氧代-1-(苯甲基)乙基]-氨基甲酸-9H-芴-9-甲酯 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 verrucine A
  参考文献：
  名称：

  Total Solid Phase Syntheses of the Quinazoline Alkaloids:  Verrucines A and B and Anacine

  摘要：

  The first total syntheses of verrucines A and B and anacine (revised structure) were accomplished on Sasrin resin. This work confirmed the structure of verrucine A and unambiguously showed verrucine B to be a derivative of D-phenylalanine and L-glutamine, The study also proved that anacine and its epimer are quinazoline alkaloids, not benzodiazepines as originally proposed. 1-Hydroxyverrucine B, derived from air oxidization of verrucine B, was also isolated and characterized.

  DOI：

  10.1021/np010342y

文献信息

• Total Solid Phase Syntheses of the Quinazoline Alkaloids:  Verrucines A and B and Anacine
  作者：Haishan Wang、Mui Mui Sim

  DOI：10.1021/np010342y

  日期：2001.12.1

  The first total syntheses of verrucines A and B and anacine (revised structure) were accomplished on Sasrin resin. This work confirmed the structure of verrucine A and unambiguously showed verrucine B to be a derivative of D-phenylalanine and L-glutamine, The study also proved that anacine and its epimer are quinazoline alkaloids, not benzodiazepines as originally proposed. 1-Hydroxyverrucine B, derived from air oxidization of verrucine B, was also isolated and characterized.