7,8-Methylenedioxy-2-phenyl-5-(3',4',5'-trimethoxyphenyl)-5,10-dihydro<1,2,4>triazolo<1,2-b>phthalazine-1,3(2H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7,8-Methylenedioxy-2-phenyl-5-(3',4',5'-trimethoxyphenyl)-5,10-dihydro<1,2,4>triazolo<1,2-b>phthalazine-1,3(2H)-dione
• 英文别名: 5-Phenyl-2-(3,4,5-trimethoxyphenyl)-12,14-dioxa-3,5,7-triazatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),9,11(15)-triene-4,6-dione
• 化学式: C₂₆H₂₃N₃O₇
• 分子量: 489.485
• InChiKey: LWQOATQRKJZACE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (benzo[d][1,3]dioxol-5-ylmethyl)trimethylsilane 在 吡啶 、 正丁基锂 、 溴 、 silica gel 、 sodium carbonate 作用下， 以 四氯化碳 、 二氯甲烷 、 水 为溶剂， 反应 123.5h， 生成 7,8-Methylenedioxy-2-phenyl-5-(3',4',5'-trimethoxyphenyl)-5,10-dihydro<1,2,4>triazolo<1,2-b>phthalazine-1,3(2H)-dione
  参考文献：
  名称：

  A practical synthesis of the anti-tumour agent 2-methyl-4-deoxyisopicropodophyllotoxin and related podophyllin analogues

  摘要：

  We describe an efficient, six-stage synthesis of 2-methyl-4-deoxyisopicropodophyllotoxin, which proceeds via a Diels-Alder cycloaddition between 2-methylmaleic anhydride and the orthoquinodimethane generated by treatment of 5-[1-acetoxy-1-(3',4',5'-trimethoxyphenyl)methyl]-6-trimethyl-silylmethyl-1,3-benzodioxole with silica gel at 60-degrees-C. The podophyllin was converted into a number of 4'-ester derivatives. This procedure was also used to prepare a diazapodophyllin via the use of 4-phenyl-1,2,4-triazoline-3,5-dione as dienophile.

  DOI：

  10.1039/p19930001235

文献信息

• A practical synthesis of the anti-tumour agent 2-methyl-4-deoxyisopicropodophyllotoxin and related podophyllin analogues
  作者：Andrew R. Beard、Sarah J. Hazell、John Mann、Christopher Palmer

  DOI：10.1039/p19930001235

  日期：——

  We describe an efficient, six-stage synthesis of 2-methyl-4-deoxyisopicropodophyllotoxin, which proceeds via a Diels-Alder cycloaddition between 2-methylmaleic anhydride and the orthoquinodimethane generated by treatment of 5-[1-acetoxy-1-(3',4',5'-trimethoxyphenyl)methyl]-6-trimethyl-silylmethyl-1,3-benzodioxole with silica gel at 60-degrees-C. The podophyllin was converted into a number of 4'-ester derivatives. This procedure was also used to prepare a diazapodophyllin via the use of 4-phenyl-1,2,4-triazoline-3,5-dione as dienophile.