2'-bromopodophyllotoxone | 37158-57-9

• 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'-bromopodophyllotoxone
• 英文别名: 2'-Brom-podophyllotoxon；(5aR,8aR,9S)-9-(2-bromo-3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxole-5,8-dione
• CAS: 37158-57-9
• 化学式: C₂₂H₁₉BrO₈
• 分子量: 491.292
• InChiKey: MNORHSVCHKJWNS-ZLIFDBKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-bromopodophyllotoxone 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 以60%的产率得到
  参考文献：
  名称：

  天然木脂素鬼臼毒素衍生的 2'(2',6')-(Di)卤代异恶唑鬼臼酸酰胺的合成及其杀螨活性

  摘要：

  In continuation of our program to discover natural product-based pesticides, a series of 2'(2',6)-(di)halogenoisoxazolopodophyllic acids-based amides were prepared by structural modification of a naturally occurring lignan podophyllotoxin. Meanwhile, their acaricidal activity was evaluated against a typically crop-threatening agricultural insect pest, Tetranychus cinnabarinus. Among all derivatives, especially compounds 10-12 displayed 4.8-7.4 folds more potent acaricidal activity than podophyllotoxin against T. cinnabarinus. This demonstrated that the carboxyl group at their C-2 position of 2'(2',6')-(di)halogenoisoxazolopodophyllic acids was very important for the acaricidal activity.

  DOI：

  10.3987/com-17-s(t)12
• 作为产物：
  描述：

  2'-bromopodophyllotoxin 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到2'-bromopodophyllotoxone
  参考文献：
  名称：

  天然木脂素鬼臼毒素衍生的 2'(2',6')-(Di)卤代异恶唑鬼臼酸酰胺的合成及其杀螨活性

  摘要：

  In continuation of our program to discover natural product-based pesticides, a series of 2'(2',6)-(di)halogenoisoxazolopodophyllic acids-based amides were prepared by structural modification of a naturally occurring lignan podophyllotoxin. Meanwhile, their acaricidal activity was evaluated against a typically crop-threatening agricultural insect pest, Tetranychus cinnabarinus. Among all derivatives, especially compounds 10-12 displayed 4.8-7.4 folds more potent acaricidal activity than podophyllotoxin against T. cinnabarinus. This demonstrated that the carboxyl group at their C-2 position of 2'(2',6')-(di)halogenoisoxazolopodophyllic acids was very important for the acaricidal activity.

  DOI：

  10.3987/com-17-s(t)12

文献信息

• Insight into dihalogenation of E-ring of podophyllotoxins, and their acyloxyation derivatives at the C4 position as insecticidal agents
  作者：Zhiping Che、Xiang Yu、Lingling Fan、Hui Xu

  DOI：10.1016/j.bmcl.2013.08.044

  日期：2013.10

  Unexpected sequential E-ring dihalogenation of podophyllotoxin analogues is reported. It demonstrated that a chlorine/bromine atom was prior introduced at the C2' position of podophyllotoxin, and the corresponding free rotation of E-ring around the C1-C1' bond of 2'-chloro or 2'-bromopodophyllotoxin was restricted. When 2'-chloro or 2'-bromopodophyllotoxin reacted with N-chlorosuccinimide (NCS), the chlorine atom was regioselectively introduced at their C6' position on the E-ring. Whereas 2'-chloro or 2'-bromopodophyllotoxin reacted with NBS, the bromine atom was regioselectively introduced at their C5 position on the B-ring. When 2'-chloropodophyllotoxin reacted with different carboxylic acids in the presence of BF3 center dot Et2O, the steric effect of its E-ring for stereoselective synthesis of 4 beta-acyloxy-2'-chloropodophyllotoxin derivatives was observed. The insecticidal activity of 2'(2',6')-(di)halogen-substituted podophyllotoxin derivatives were evaluated with Mythimna separata Walker. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis Of 2′(2′,6′)-(Di)Halogenoisoxazolopodophyllic Acids-Based Amides Derived from a Naturally Occurring Lignan Podophyllotoxin and Their Acaricidal Activity
  作者：Hui Xu、Min Lv、Bingchuan Zhang、Mingqiao Yu

  DOI：10.3987/com-17-s(t)12

  日期：——

  In continuation of our program to discover natural product-based pesticides, a series of 2'(2',6)-(di)halogenoisoxazolopodophyllic acids-based amides were prepared by structural modification of a naturally occurring lignan podophyllotoxin. Meanwhile, their acaricidal activity was evaluated against a typically crop-threatening agricultural insect pest, Tetranychus cinnabarinus. Among all derivatives, especially compounds 10-12 displayed 4.8-7.4 folds more potent acaricidal activity than podophyllotoxin against T. cinnabarinus. This demonstrated that the carboxyl group at their C-2 position of 2'(2',6')-(di)halogenoisoxazolopodophyllic acids was very important for the acaricidal activity.