N-trityl-verrucine B | 387877-71-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-trityl-verrucine B
• 英文别名: (1R,4S)-1,3,4,6-tetrahydro-3,6-dioxo-1-(phenylmethyl)-2H-pyrazino[2,1-b]quinazoline-4-(N-trityl)propanamide；3-[(1R,4S)-1-benzyl-3,6-dioxo-2,4-dihydro-1H-pyrazino[2,1-b]quinazolin-4-yl]-N-tritylpropanamide
• CAS: 387877-71-6
• 化学式: C₄₀H₃₄N₄O₃
• 分子量: 618.735
• InChiKey: CNRDWGFSUNMYGR-GPOMZPHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  47
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  90.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-trityl-verrucine B 在 三乙基硅烷 、 air 、 三氟乙酸 作用下， 以 甲醇 、 氘代二甲亚砜 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (1S,4S)-1,3,4,6-tetrahydro-3,6-dioxo-1-hydroxy-1-(phenylmethyl)-2H-pyrazino[2,1-b]quinazoline-4-propanamide
  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
• 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 、 邻氨基苯甲酸 、 alkaline earth salt of/the/ methylsulfuric acid 以17%的产率得到N-trityl-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.