2-Methyl-4-deoxyisopicropodophyllotoxin | 97185-04-1

• 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: 2-Methyl-4-deoxyisopicropodophyllotoxin
• 英文别名: 2-methylisodeoxypicrophyllotoxin
• CAS: 97185-04-1；113597-15-2；113627-24-0；115509-58-5
• 化学式: C₂₃H₂₄O₇
• 分子量: 412.439
• InChiKey: KJDLIJGBYOEPOA-MHALITNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-Methyl-4-deoxyisopicropodophyllotoxin 在 氢溴酸 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 72.0h， 以53%的产率得到2-Methyl-4-deoxy-4'-demethylisopicropodophyllotoxin
  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
• 作为产物：
  描述：

  (benzo[d][1,3]dioxol-5-ylmethyl)trimethylsilane 在 吡啶 、 sodium hydroxide 、 正丁基锂 、 双氧水 、 溴 、 silica gel 、 sodium carbonate 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氯化碳 、 二氯甲烷 、 水 为溶剂， 反应 272.0h， 生成 2-Methyl-4-deoxyisopicropodophyllotoxin
  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

• The synthesis of structural analogues of the podophyllum lignans: selective wittig reactions on 1-aryl-2-methyl-tetrahydronaphthoic acid anhydride
  作者：John Mann、Lilan T.F. Wong、Andrew R. Beard

  DOI：10.1016/s0040-4039(00)98580-0

  日期：1985.1

  The title anhydride reacts with stabilised phosphorus ylids exclusively at the carbonyl remote from the 1-aryl substituent. These products have been converted into a variety of compounds related in structure to deoxyisopicrophyllotoxin.

  标题酸酐仅在远离1-芳基取代基的羰基上与稳定的磷基反应。这些产物已被转化成与脱氧异鬼臼毒素有关的各种化合物。
• Synthesis of analogues of 4-deoxypodophyllotoxin
  作者：Andrrew R. Beard、Michael G.B. Drew、John Mann、Lilan T.F. Wong(née Yeung)

  DOI：10.1016/s0040-4020(01)83462-1

  日期：1987.1