3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride | 95458-29-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride
• 英文别名: (5R,5aR,8aS)-8a-methyl-5-(3,4,5-trimethoxyphenyl)-5a,9-dihydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxole-6,8-dione
• CAS: 95458-29-0
• 化学式: C₂₃H₂₂O₈
• 分子量: 426.423
• InChiKey: SRMZZKDKBLXRFU-MSYCTHLASA-N

物化性质

• 沸点：
  575.8±50.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5R,5aR,8aS)-5a-methyl-5-(3,4,5-trimethoxyphenyl)-8a,9-dihydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxole-6,8-dione 、 3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride 生成 (5R,5aR,8aS)-5a-methyl-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
  参考文献：
  名称：

  BEARD, ANDREW R.;DREW, MICHAEL G. B.;MANN, JOHN;WONG, LILAN T. F., TETRAHEDRON, 43,(1987) N 18, 4207-4215

  摘要：

  DOI：
• 作为产物：
  描述：

  胡椒醇 在 吡啶 、 正丁基锂 、 氢溴酸 、 溴 、 silica gel 、 sodium carbonate 、 magnesium 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 为溶剂， 反应 269.5h， 生成 3-methyl-6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2,3-naphthoic anhydride
  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

• Mann, John; Piper, Susan E.; Yeung, Lilan K.P., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2081 - 2088
  作者：Mann, John、Piper, Susan E.、Yeung, Lilan K.P.

  DOI：——

  日期：——
• MANN, J.;PIPER, S. E.;YEUNG, L. K. P., J. CHEM. SOC. PERKIN TRANS., 1984, N 9, 2081-2088
  作者：MANN, J.、PIPER, S. E.、YEUNG, L. K. P.

  DOI：——

  日期：——
• BEARD, ANDREW R.;DREW, MICHAEL G. B.;MANN, JOHN;WONG, LILAN T. F., TETRAHEDRON, 43,(1987) N 18, 4207-4215
  作者：BEARD, ANDREW R.、DREW, MICHAEL G. B.、MANN, JOHN、WONG, LILAN T. F.

  DOI：——

  日期：——
• 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.