4alpha-Benzyloxy-2-chloropodophyllotoxin | 1246849-25-1

• 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: 4alpha-Benzyloxy-2-chloropodophyllotoxin
• 英文别名: (5R,5aS,8aR,9R)-5a-chloro-9-phenylmethoxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
• CAS: 1246849-25-1
• 化学式: C₂₉H₂₇ClO₈
• 分子量: 538.982
• InChiKey: XVGPQPYUVDTDBH-CLIKSALWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-chloropodophyllotoxin 、 苯甲醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到4alpha-Benzyloxy-2-chloropodophyllotoxin
  参考文献：
  名称：

  Natural products-based insecticidal agents 7. Semisynthesis and insecticidal activity of novel 4α-alkyloxy-2-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo

  摘要：

  In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 16 novel 4 alpha-alkyloxy-2-chloropodophyllotoxin derivatives were semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Among all the tested derivatives, especially compounds 4b, 4e, 4g, and 4p exhibited more promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach. Generally, it was obviously demonstrated that the length of straight-chain or branched-chain alkyloxy, and heteroatom-containing cycloalkyloxy at the C-4 position of 2-chloropodophyllotoxin were very important for the insecticidal activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.050

文献信息

• Natural products-based insecticidal agents 7. Semisynthesis and insecticidal activity of novel 4α-alkyloxy-2-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo
  作者：Hui Xu、Xiao Xiao、Qing-tian Wang

  DOI：10.1016/j.bmcl.2010.07.050

  日期：2010.9

  In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 16 novel 4 alpha-alkyloxy-2-chloropodophyllotoxin derivatives were semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Among all the tested derivatives, especially compounds 4b, 4e, 4g, and 4p exhibited more promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach. Generally, it was obviously demonstrated that the length of straight-chain or branched-chain alkyloxy, and heteroatom-containing cycloalkyloxy at the C-4 position of 2-chloropodophyllotoxin were very important for the insecticidal activity. (C) 2010 Elsevier Ltd. All rights reserved.