(Z)-3-methoxy-5-hydroxy- stilbene | 143207-76-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-3-methoxy-5-hydroxy- stilbene
• 英文别名: (Z)-3-hydroxy-5-methoxystilbene；3-methoxy-5-[(Z)-2-phenylethenyl]phenol
• CAS: 143207-76-5
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: JVIXPWIEOVZVJC-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三苯基苄基溴化膦 在 sodium methylate 、 三溴化硼 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 24.0h， 生成 (Z)-3-methoxy-5-hydroxy- stilbene
  参考文献：
  名称：

  Endogenous pine wood nematicidal substances in pines, Pinus massoniana, P. strobus and P. palustris

  摘要：

  The presence of the repellents and nematicides to the pine wood nematode, Bursaphelenchus xylophilus, was found in the heartwood and bark of Pinus massoniana, P. strobus and P. palustris, which have a resistance to the pine wood nematode. The heartwood of P. massoniana contained a repellent, alpha-humulene and two nematicidal substances, pinosylvin monomethylether (PSM) and (-)-nortrachelogenin for the nematode. The bark of the pine contained two nematicides, methyl ferulate and (+)-pinoresinol. PSM, which showed the highest nematicidal activity (LD50 was 4 ppm), was also contained in the heartwood of P. strobus and the heartwood and bark of P. palustris. The resistance of these pines to the pine wood nematode is considered to be attributed to the presence of these endogenously defending substances. Further, the relationship between the structure and the nematicidal activity was elucidated for PSM and methyl ferulate. Moreover, PSM showed little anti-acetylcholinesterase activity.

  DOI：

  10.1016/0031-9422(93)85098-c

文献信息

• Synthesis and Nematocidal Activity of Hydroxystilbenes
  作者：Mohammad Ahad ALI、Kaoru KONDO、Yoshisuke TSUDA

  DOI：10.1248/cpb.40.1130

  日期：1992.5.25

  Various (E)-hydroxystilbenes were synthesized from (E)/(Z) mixtures of methoxystilbenes through a new (Z)-(E) isomerization method followed dy demethylation. The nematocidal activity appears when methoxystilbenes are demethylated to hydroxystilbenes. For this activity, a hydroxy group at the C-2 or C-3 position is necessary. Thus, 2-hydroxy-, 3-hydroxy-, 2, 6-dihydroxy-, 3, 4-dihydroxy-, 3, 5-dihydroxy-, 2, 2'-dihydroxy-, 3, 3'-dihydroxy-, 3, 4'-dihydroxy-, 2-hydroxy-4-methoxy-, 5-hydroxy-2-methoxy-, 2-hydroxy-6-methoxy-, 6-allyloxy-2-hydroxy-, 3-hydroxy-5-methoxy-, and 5-allyloxy-3-hydroxystilbenes showed rather potent nematocidal activity. The activity of 5-allyloxy-3-hydroxystilbene was the strongest [minimal lethal concentration (MLC)=30 μM]. The activities of the (E) and (Z) isomers were comparable. The activities were also retained, though they were weaker, in the dihydro derivatives, hydroxybibenzyls.

  通过一种新的(Z)-(E)异构化方法随后进行脱甲基反应，从(E)/(Z)混合甲氧基二苯乙烯中合成了多种(E)-羟基二苯乙烯。当甲氧基二苯乙烯脱甲基生成羟基二苯乙烯时，表现出杀线虫活性。为了产生这种活性，C-2或C-3位置上必须有一个羟基。因此，2-羟基-、3-羟基-、2,6-二羟基-、3,4-二羟基-、3,5-二羟基-、2,2'-二羟基-、3,3'-二羟基-、3,4'-二羟基-、2-羟基-4-甲氧基-、5-羟基-2-甲氧基-、2-羟基-6-甲氧基-、6-烯丙氧基-2-羟基-、3-羟基-5-甲氧基-和5-烯丙氧基-3-羟基二苯乙烯表现出相当强的杀线虫活性。5-烯丙氧基-3-羟基二苯乙烯的活性最强[最小致死浓度（MLC）=30 μM]。(E)和(Z)异构体的活性相当。二氢衍生物，羟基联苄中也保留了这些活性，尽管较弱。
• US5314693A
  申请人：——

  公开号：US5314693A

  公开（公告）日：1994-05-24