N-[(E)-[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienylidene]amino]-2-ethoxybenzamide | 1443225-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-[(E)-[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienylidene]amino]-2-ethoxybenzamide
• CAS: 1443225-00-0
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: QLEIPRYDPBHSHV-PZCMRWPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  69.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  胡椒碱 在 manganese(IV) oxide 、 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 硫酸 、 溶剂黄146 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 40.0h， 生成 N-[(E)-[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienylidene]amino]-2-ethoxybenzamide 、 N'-((1Z,2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-dien-1-ylidene)-2-ethoxybenzohydrazide
  参考文献：
  名称：

  Natural-product-based insecticidal agents 14. Semisynthesis and insecticidal activity of new piperine-based hydrazone derivatives against Mythimna separata Walker in vivo

  摘要：

  In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, twenty-six new piperine-based hydrazone derivatives were synthesized from piperine, an alkaloid isolated from Piper nigrum Linn. The single-crystal structures of 6c, 6q and 6w were unambiguously confirmed by X-ray crystallography. Their insecticidal activity was evaluated against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 6b, 6i and 6r, the final mortality rates of which, at the concentration of 1 mg/mL, were 62.1%, 65.5% and 65.5%, respectively, exhibited more pronounced insecticidal activity compared to toosendanin at 1 mg/mL, a commercial botanical insecticide isolated from Melia azedarach. It suggested that introduction of the substituents at the C-2 position on the phenyl ring of the hydrazone derivatives was important for their insecticidal activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.053

文献信息

• Natural-product-based insecticidal agents 14. Semisynthesis and insecticidal activity of new piperine-based hydrazone derivatives against Mythimna separata Walker in vivo
  作者：Huan Qu、Xiang Yu、Xiaoyan Zhi、Min Lv、Hui Xu

  DOI：10.1016/j.bmcl.2013.08.053

  日期：2013.10

  In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, twenty-six new piperine-based hydrazone derivatives were synthesized from piperine, an alkaloid isolated from Piper nigrum Linn. The single-crystal structures of 6c, 6q and 6w were unambiguously confirmed by X-ray crystallography. Their insecticidal activity was evaluated against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 6b, 6i and 6r, the final mortality rates of which, at the concentration of 1 mg/mL, were 62.1%, 65.5% and 65.5%, respectively, exhibited more pronounced insecticidal activity compared to toosendanin at 1 mg/mL, a commercial botanical insecticide isolated from Melia azedarach. It suggested that introduction of the substituents at the C-2 position on the phenyl ring of the hydrazone derivatives was important for their insecticidal activity. (C) 2013 Elsevier Ltd. All rights reserved.