methyl (5R,6S,7R)-7-formyl-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate | 171483-28-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: methyl (5R,6S,7R)-7-formyl-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate
• CAS: 171483-28-6
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: SLFDZSGCEBRAPV-LVXYXVKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• 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：

  methyl (5R,6S,7R)-7-formyl-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate 生成 deoxypicropodophyllinic acid methyl ester
  参考文献：
  名称：

  JONES, DAVID W.;THOMPSON, ADRIAN M., J. CHEM. SOC. CHEM. COMMUN.,(1988) N 16, C. 1095-1096

  摘要：

  DOI：
• 作为产物：
  描述：

  去氧鬼臼毒素 在 氢氧化钾 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.0h， 生成 methyl (5R,6S,7R)-7-formyl-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate
  参考文献：
  名称：

  Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring

  摘要：

  Several cyclolignans lacking of the lactone moiety can easily be prepared from naturally occurring lignans such as podophyllotoxin and deoxypodophyllotoxin by simple chemical transformations. Their cytotoxicity has been studied in four tumoral cell lines. Most of the compounds show similar effects in all the neoplastic systems tested, except the aldehyde 9 (methyl 9-deoxy-9-oxo-alpha-apopicropodophyllate) and the hydrazones 16 and 17 which show a highly selective cytotoxicity towards HT-29 human colon carcinoma. Additionally, several molecular modeling studies have been done with aldehyde 9 and the corresponding saturated aldehyde 13 in comparison with podophyllotoxin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10042-4

文献信息

• 13C NMR data for 7- and/or 9-aza-substituted naphthalenecyclolignans
  作者：M. Angeles Castro、José M. Miguel del Corral、M. Luisa López-Vázquez、Pablo A. García、Arturo San Feliciano、Marina Gordaliza

  DOI：10.1002/(sici)1097-458x(199711)35:11<808::aid-omr165>3.0.co;2-l

  日期：1997.11

  C-13 NMR assignments are provided for 45 7- and/or 9-aza-substituted naphthalenecyclolignans. (C) 1997 John Wiley & Sons, Ltd.