5-[(1Z)-2-phenylethenyl]benzene-1,3-diol | 106325-78-4

• 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: 5-[(1Z)-2-phenylethenyl]benzene-1,3-diol
• 英文别名: (Z)-5-styrylbenzene-1,3-thiol；(Z)-5-styrylbenzene-1,3-diol；cis-3,5-dihydroxystilbene；cis-pinosylvin；pinosylvine；5-[(Z)-2-phenylethenyl]benzene-1,3-diol
• CAS: 106325-78-4
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: YCVPRTHEGLPYPB-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-[(1Z)-2-phenylethenyl]benzene-1,3-diol 在 二苯二硫醚 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以99%的产率得到赤松素
  参考文献：
  名称：

  New Method for Isomerization of (Z)-Stilbenes into the (E)-Isomers Catalyzed by Diaryl Disulfide.

  摘要：

  在二芳基二硫化物的催化下，开发出了一种将(Z)-二苯乙烯异构化为(E)-异构体的新方法。二苯基二硫醚是用途最广的催化剂，可顺利实现二苯乙烯、甲氧基二苯乙烯和羟基二苯乙烯的异构化。对于二甲氧基二苯乙烯，二苯基二硫醚的异构化速度较慢，而 4，4'-二硝基二苯基二硫醚或 2，2'-二吡啶基二硫醚则能很好地完成异构化。二苯基二硫化物对带有引电子取代基的二苯乙烯的异构化无效。带有电子捐赠取代基的催化剂（如 4，4'-二甲氧基二苯基二硫醚）可大大加速这些二苯乙烯的异构化。

  DOI：

  10.1248/cpb.40.2842
• 作为产物：
  描述：

  [[3,5-二[[(叔丁基)二甲基硅烷基]氧基]苯基]甲基]三苯基氯化鏻 在 正丁基锂 、 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 8.5h， 生成 5-[(1Z)-2-phenylethenyl]benzene-1,3-diol
  参考文献：
  名称：

  Synthesis of natural polyhydroxystilbenes

  摘要：

  DOI：

  10.1016/s0040-4020(01)90559-9

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。
• Algicidal Activity of Stilbene Analogues
  作者：Cassia S. Mizuno、Kevin K. Schrader、Agnes M. Rimando

  DOI：10.1021/jf801988p

  日期：2008.10.8

  Continuing our search for natural product and natural product-based compounds for the control of off-flavor in catfish, 29 stilbene analogues were synthesized and evaluated for algicidal activity against the 2-methylisoborneol (MIB)-producing cyanobacterium Oscillatoria perornata. The cis and trans isomers of 4-(3,5-dimethoxystyryl)aniline showed moderate and selective algicidal activity toward O.

  在继续寻找天然产物和基于天然产物的化合物以控制cat鱼异味的过程中，合成了29种二苯乙烯类似物并评估了其对生产2-甲基异冰片醇（MIB）的蓝细菌Oscillatoria perornata的杀藻活性。4-（3,5-二甲氧基苯乙烯基）苯胺的顺式和反式异构体表现出对O. perornata的适度和选择性杀藻活性，观察到的最低抑菌浓度和最低的完全抑菌浓度为10μM。这是关于二甲sti对产生MIB的蓝细菌物种的选择性杀藻活性的首次报道。
• Endogenous pine wood nematicidal substances in pines, Pinus massoniana, P. strobus and P. palustris
  作者：Takayuki Suga、Shinji Ohta、Kiyotaka Munesada、Nagatoshi Ide、Masako Kurokawa、Masahiro Shimizu、Emi Ohta

  DOI：10.1016/0031-9422(93)85098-c

  日期：1993.8

  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.
• US5314693A
  申请人：——

  公开号：US5314693A

  公开（公告）日：1994-05-24
• Synthesis of natural polyhydroxystilbenes
  作者：Ma. uz Cardona、Ma. Isabel Fernandez、Ma. Begon̄a Garcia、Jose R. Pedro

  DOI：10.1016/s0040-4020(01)90559-9

  日期：1986.1