[(5R,5aR,8aR,9R)-9-(3,4-dihydroxy-5-methoxyphenyl)-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] acetate | 646520-17-4

• 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: [(5R,5aR,8aR,9R)-9-(3,4-dihydroxy-5-methoxyphenyl)-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] acetate
• CAS: 646520-17-4
• 化学式: C₂₂H₂₀O₉
• 分子量: 428.395
• InChiKey: MPZRADIPKZSRGD-UXOGBEFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2-二溴乙烷 、 [(5R,5aR,8aR,9R)-9-(3,4-dihydroxy-5-methoxyphenyl)-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] acetate 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以68%的产率得到(5R,5aR,8aR,9R)-9-acetoxy-5-(8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
  参考文献：
  名称：

  Synthesis, cytotoxicity and antiviral activity of podophyllotoxin analogues modified in the E-ring

  摘要：

  Several podophyllotoxin derivatives modified in the E-ring were prepared and evaluated for their cytotoxicity on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28) and for their antiherpetic activity against Herpes simplex virus type II. The trimethoxyphenyl moiety was oxidized to ortho-quinone and further condensed with diamines and enamines to form different heterocycles. Most of the compounds maintained their cytotoxicity at the muM level and some of them showed antiherpetic activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.05.001
• 作为产物：
  描述：

  (5R,5aR,8aR,9R)-8-羰基-9-(3,4,5-三甲氧苯基)-5,5a,6,8,8a,9-六氢呋喃并[3',4':6,7]萘并[2,3-d][1,3]二噁唑-5-基乙酸酯 在 硝酸 、 溶剂黄146 、 丙酸 作用下， 以 乙醇 为溶剂， 反应 0.07h， 生成 [(5R,5aR,8aR,9R)-9-(3,4-dihydroxy-5-methoxyphenyl)-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] acetate
  参考文献：
  名称：

  Synthesis, cytotoxicity and antiviral activity of podophyllotoxin analogues modified in the E-ring

  摘要：

  Several podophyllotoxin derivatives modified in the E-ring were prepared and evaluated for their cytotoxicity on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28) and for their antiherpetic activity against Herpes simplex virus type II. The trimethoxyphenyl moiety was oxidized to ortho-quinone and further condensed with diamines and enamines to form different heterocycles. Most of the compounds maintained their cytotoxicity at the muM level and some of them showed antiherpetic activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.05.001