2-O-[(5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] 1-O-methyl 3-nitrobenzene-1,2-dicarboxylate | 1244966-28-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 2-O-[(5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] 1-O-methyl 3-nitrobenzene-1,2-dicarboxylate
• CAS: 1244966-28-6
• 化学式: C₃₁H₂₇NO₁₃
• 分子量: 621.554
• InChiKey: UTLOYCVTEIDWHM-PWXWPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  171
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  3-硝基-2-羧基苯甲酸甲酯 、 鬼臼毒素 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-O-[(5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] 1-O-methyl 3-nitrobenzene-1,2-dicarboxylate
  参考文献：
  名称：

  Natural products-based insecticidal agents 6. Design, semisynthesis, and insecticidal activity of novel monomethyl phthalate derivatives of podophyllotoxin against Mythimna separata Walker in vivo

  摘要：

  To discover the more potent analogs, 12 novel monomethyl phthalate derivatives of podophyllotoxin were synthesized and preliminarily tested against the pre-third-instar larvae of Mythimna separata Walker in vivo at the concentration of 1 mg/mL. Compounds 8e-i showed the higher insecticidal activity than podophyllotoxin. Especially 8g exhibited the most potent insecticidal activity compared with toosendanin, a commercially available insecticide derived from Melia azedarach. The structure-activity relationships demonstrated that trans-lactone, 4 beta-substitution, 2 beta-chlorine substitution, and 4'-methoxy group were the important structural properties of podophyllotoxins for good insecticidal activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.032

文献信息

• Natural products-based insecticidal agents 6. Design, semisynthesis, and insecticidal activity of novel monomethyl phthalate derivatives of podophyllotoxin against Mythimna separata Walker in vivo
  作者：Hui Xu、Xiao-Qiang He

  DOI：10.1016/j.bmcl.2010.06.032

  日期：2010.8

  To discover the more potent analogs, 12 novel monomethyl phthalate derivatives of podophyllotoxin were synthesized and preliminarily tested against the pre-third-instar larvae of Mythimna separata Walker in vivo at the concentration of 1 mg/mL. Compounds 8e-i showed the higher insecticidal activity than podophyllotoxin. Especially 8g exhibited the most potent insecticidal activity compared with toosendanin, a commercially available insecticide derived from Melia azedarach. The structure-activity relationships demonstrated that trans-lactone, 4 beta-substitution, 2 beta-chlorine substitution, and 4'-methoxy group were the important structural properties of podophyllotoxins for good insecticidal activity. (C) 2010 Elsevier Ltd. All rights reserved.