4',5'-didemethoxy-4',5'-dioxoepipodophyllotoxin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 4',5'-didemethoxy-4',5'-dioxoepipodophyllotoxin
• 英文别名: 4′,5′-didemethoxy-4′,5′-dioxoepipodophyllotoxin；5-[(5S,5aR,8aR,9R)-5-hydroxy-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-9-yl]-3-methoxycyclohexa-3,5-diene-1,2-dione
• 化学式: C₂₀H₁₆O₈
• 分子量: 384.342
• InChiKey: XCOKRODRXOWJQI-HQKIHSOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4',5'-didemethoxy-4',5'-dioxoepipodophyllotoxin 在 吡啶 、 chromium(VI) oxide 、 盐酸羟胺 、 sodium acetate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 73.5h， 生成
  参考文献：
  名称：

  Synthesis and insecticidal activity of new oxime derivatives of podophyllotoxin-based phenazines against Mythimna separata Walker

  摘要：

  To discover new natural-product-based insecticidal agents, a series of novel oxime derivatives of podophyllotoxin-based phenazines modified in the C, D and E rings of podophyllotoxin were prepared and tested as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. The steric configuration of IIIc was unambiguously confirmed by single-crystal X-ray diffraction analysis. Compounds IIIa-d, and IIIi exhibited an equal or higher insecticidal activity than toosendanin. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.081
• 作为产物：
  描述：

  5,8,8a,9-四氢-9-羟基-5-(3,4,5-三甲氧基苯基)-(5R,5aR,8aR,9S)-呋喃并[3',4':6,7]萘并[2,3-d]-1,3-二氧杂环戊烯-6(5aH)-酮 生成 4',5'-didemethoxy-4',5'-dioxoepipodophyllotoxin
  参考文献：
  名称：

  AYRES, DAVID C.;RITCHIE, TIMOTHY J., J. CHEM. SOC. PERKIN TRANS. PT I,(1988) N 9, C. 2573-2578

  摘要：

  DOI：

文献信息

• Synthesis of 4β-acyloxypodophyllotoxin analogs modified in the C and E rings as insecticidal agents against Mythimna separata Walker
  作者：Xiaoyan Zhi、Xiang Yu、Chun Yang、Guodong Ding、Hui Chen、Hui Xu

  DOI：10.1016/j.bmcl.2013.12.105

  日期：2014.2

  To discover the new natural-product-based insecticidal agents, four series of sixty novel 4 beta-acyloxypodophyllotoxin analogs modified in the C and E rings were prepared, and their insecticidal activity was tested against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at the concentration of 1 mg/mL. It demonstrated that the position of the dioxo group on the E-ring of 4'-demethylepipodophyllotoxin was regioselectively controlled by the chlorine atom at its C-2' position when 2'-chloro-4'-demethylepipodophyllotoxin was oxidized by sodium periodate. Among all the derivatives, IIIi exhibited the best potent insecticidal activity with the final mortality rate of 63.3%. To alkylacyloxy series, the proper length of the side chain at the C-4 position of Ia-g, IIa-g and IIIa-g was important for their insecticidal activity. (C) 2013 Elsevier Ltd. All rights reserved.
• AYRES, DAVID C.;RITCHIE, TIMOTHY J., J. CHEM. SOC. PERKIN TRANS. PT I,(1988) N 9, C. 2573-2578
  作者：AYRES, DAVID C.、RITCHIE, TIMOTHY J.

  DOI：——

  日期：——
• Synthesis and insecticidal activity of new oxime derivatives of podophyllotoxin-based phenazines against Mythimna separata Walker
  作者：Xiaoyan Zhi、Chun Yang、Xiang Yu、Hui Xu

  DOI：10.1016/j.bmcl.2014.10.081

  日期：2014.12

  To discover new natural-product-based insecticidal agents, a series of novel oxime derivatives of podophyllotoxin-based phenazines modified in the C, D and E rings of podophyllotoxin were prepared and tested as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. The steric configuration of IIIc was unambiguously confirmed by single-crystal X-ray diffraction analysis. Compounds IIIa-d, and IIIi exhibited an equal or higher insecticidal activity than toosendanin. (C) 2014 Elsevier Ltd. All rights reserved.