9-(4-methoxybenzylamino)-5-[2-(4-methoxybenzylamino)pyrimidin-4-yl]pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine | 330823-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 9-(4-methoxybenzylamino)-5-[2-(4-methoxybenzylamino)pyrimidin-4-yl]pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine
• 英文别名: N-[(4-methoxyphenyl)methyl]-8-[2-[(4-methoxyphenyl)methylamino]pyrimidin-4-yl]-1,3,12-triazatricyclo[7.4.0.02,7]trideca-2(7),3,5,8,10,12-hexaen-13-amine
• CAS: 330823-25-1
• 化学式: C₃₀H₂₇N₇O₂
• 分子量: 517.59
• InChiKey: LKJKRIBSUDISHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  98.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(4-methoxybenzylamino)-5-[2-(4-methoxybenzylamino)pyrimidin-4-yl]pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine 在 三氟甲磺酸 作用下， 反应 2.5h， 以88%的产率得到Deoxyvariolin B
  参考文献：
  名称：

  Concise Total Syntheses of Variolin B and Deoxyvariolin B

  摘要：

  The total synthesis of the marine alkaloid variolin B has been achieved in 8 steps and 17% overall yield, starting from commercially available 4-chloro-2-methylthiopyrimidine. The key reaction involves the tandem deoxygenation and cyclization of a triarylmethanol using a combination of triethylsilane and trifluoroacetic acid. In addition, the deoxygenated analogue was prepared in 6 steps and 23% overall yield, starting from the same starting material.

  DOI：

  10.1021/jo050523v
• 作为产物：
  描述：

  (2-chloropyridin-3-yl)bis-[2-(methylsulfanyl)pyrimidin-4-yl]methanol 在 间氯过氧苯甲酸 、 三氟乙酸 作用下， 生成 9-(4-methoxybenzylamino)-5-[2-(4-methoxybenzylamino)pyrimidin-4-yl]pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine
  参考文献：
  名称：

  研究水杨酸酯的全合成：快速进入核心结构

  摘要：

  variolins的吡啶并[3'，2'：4,5]吡咯并[1,2- c ]嘧啶核心结构是由市售材料分三步合成的。关键反应涉及使用三乙基硅烷和三氟乙酸的组合使三芳基甲醇脱氧并伴随环化。天然产物所需的胺官能团的引入已通过两个步骤完成。

  DOI：

  10.1016/s0040-4039(00)01772-x

文献信息

• Studies toward the total synthesis of the variolins: rapid entry to the core structure
  作者：Regan J Anderson、Jonathan C Morris

  DOI：10.1016/s0040-4039(00)01772-x

  日期：2001.1

  The pyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine core structure of the variolins has been synthesized in three steps from commercially available materials. The key reaction involves the deoxygenation and concomitant cyclization of a triarylmethanol using the combination of triethylsilane and trifluoroacetic acid. Introduction of amine functionality as required for the natural products has been achieved

  variolins的吡啶并[3'，2'：4,5]吡咯并[1,2- c ]嘧啶核心结构是由市售材料分三步合成的。关键反应涉及使用三乙基硅烷和三氟乙酸的组合使三芳基甲醇脱氧并伴随环化。天然产物所需的胺官能团的引入已通过两个步骤完成。
• VARIOLIN DERIVATIVES AS ANTI-CANCER AGENTS
  申请人：PHARMA MAR, S.A.

  公开号：EP1299388B1

  公开（公告）日：2009-05-13
• US7320981B2
  申请人：——

  公开号：US7320981B2

  公开（公告）日：2008-01-22
• Concise Total Syntheses of Variolin B and Deoxyvariolin B
  作者：Regan J. Anderson、Jonathan B. Hill、Jonathan C. Morris

  DOI：10.1021/jo050523v

  日期：2005.8.1

  The total synthesis of the marine alkaloid variolin B has been achieved in 8 steps and 17% overall yield, starting from commercially available 4-chloro-2-methylthiopyrimidine. The key reaction involves the tandem deoxygenation and cyclization of a triarylmethanol using a combination of triethylsilane and trifluoroacetic acid. In addition, the deoxygenated analogue was prepared in 6 steps and 23% overall yield, starting from the same starting material.