2-(Hydroxymethyl)phenyl benzenesulfonate | 664315-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(Hydroxymethyl)phenyl benzenesulfonate
• 英文别名: [2-(hydroxymethyl)phenyl] benzenesulfonate
• CAS: 664315-53-1
• 化学式: C₁₃H₁₂O₄S
• 分子量: 264.302
• InChiKey: NOCQOUGJRZKCSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Hydroxymethyl)phenyl benzenesulfonate 、 2-chloropodophyllotoxin 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到[2-[[(5R,5aS,8aR,9R)-5a-chloro-6-oxo-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]oxymethyl]phenyl] benzenesulfonate
  参考文献：
  名称：

  Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-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, 14 novel 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxin derivatives were stereoselectively semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 9c' and 9g' exhibited the most promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach at 1 mg/mL. Generally, it was preliminarily demonstrated that arylsulfonyloxy groups at the C-2 position of benzyloxy moiety and the length of the side chain on the benzenesulfonyloxy group of 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxins might be important for the insecticidal activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.075
• 作为产物：
  描述：

  2-甲酰基苯基苯磺酸盐 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 2-(Hydroxymethyl)phenyl benzenesulfonate
  参考文献：
  名称：

  Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-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, 14 novel 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxin derivatives were stereoselectively semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 9c' and 9g' exhibited the most promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach at 1 mg/mL. Generally, it was preliminarily demonstrated that arylsulfonyloxy groups at the C-2 position of benzyloxy moiety and the length of the side chain on the benzenesulfonyloxy group of 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxins might be important for the insecticidal activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.075

文献信息

• Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo
  作者：Hui Xu、Jun-Liang Zhang

  DOI：10.1016/j.bmcl.2011.07.075

  日期：2011.9

  In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 14 novel 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxin derivatives were stereoselectively semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 9c' and 9g' exhibited the most promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach at 1 mg/mL. Generally, it was preliminarily demonstrated that arylsulfonyloxy groups at the C-2 position of benzyloxy moiety and the length of the side chain on the benzenesulfonyloxy group of 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxins might be important for the insecticidal activity. (C) 2011 Elsevier Ltd. All rights reserved.