(E)-3-羟基-5-甲氧基二苯乙烯 | 35302-70-6

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (E)-3-羟基-5-甲氧基二苯乙烯
• 英文名称: 3-methoxy-5-[(E)-2-phenylvinyl]phenol
• 英文别名: 3-methoxy-5-[(1E)-2-phenylethenyl]-phenol；3-methoxy-5-hydroxy-trans-stilbene；5-hydroxy-3-methoxy-trans-stilbene；3'-hydroxy-5'-methoxystilbene；(E)-3-methoxy-5-styrylphenol；3-hydroxy-5-methoxystilbene；Pinosylvin methyl ether；3-methoxy-5-[(E)-2-phenylethenyl]phenol
• CAS: 35302-70-6
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: JVIXPWIEOVZVJC-BQYQJAHWSA-N

物化性质

• 熔点：
  119 - 121°C
• 溶解度：
  可溶于苯（微量）、DMSO（微量）、甲醇（微量）、吡啶（微量）

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

安全信息

• 危险品标志：
  Xn,N
• 安全说明：
  S26,S61
• 危险类别码：
  R22,R36,R51/53
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-羟基-5-甲氧基二苯乙烯 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 2.0h， 生成 1,3-二甲氧基-5-(2-苯基乙基)苯
  参考文献：
  名称：

  来自地草 Radula kojana 的异戊二烯联苯

  摘要：

  摘要 14 种新的联苄衍生物与两种先前已知的双（联苄）及其光谱和化学证据表征的结构一起从苔草 Radula kojana 中分离出来。七种新联苄、3,5-二羟基-2-(3-甲基-2-丁烯基)-、3-甲氧基-5-羟基-2-(3-甲基-2-丁烯基)-、3-羟基-5-甲氧基-2-(3-甲基-2-丁烯基)-和2-香叶基-3,5-二羟基联苯，2,2-二甲基-7-甲氧基-5-(2-苯乙基)-, 2,2-二甲基- 5-甲氧基-7-(2-苯乙基)-和2-甲基-2-(4-甲基-3-戊烯基)-7-甲氧基-5-(2-苯乙基)色烯已由松香素及其二甲醚合成. 3,5-Dihydroxy-2-(3-methyl-2-butenyl)- 和 2-geranyl-3,5-dihydroxybibenzyls 显示出 5-脂氧合酶和钙调素抑制活性。属于 Odontoradula 亚属的 Radula kojana 在化学上与

  DOI：

  10.1016/0031-9422(91)84129-g
• 作为产物：
  描述：

  苯基膦酸二乙酯 在 sodium methylate 、 三溴化硼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-3-羟基-5-甲氧基二苯乙烯
  参考文献：
  名称：

  Synthesis and inhibitory effects of pinosylvin derivatives on prostaglandin E2 production in lipopolysaccharide-induced mouse macrophage cells

  摘要：

  A series of natural stilbenoids, pinosylvin and its derivatives, were synthesized and evaluated for the inhibitory activity of prostaglandin E, production in lipopolysaccharide-induced RAW 264.7 cells. Potential inhibitors, including 3,5-dimethoxy-trans-stilbene and 3-hydroxy-5-benzyloxy-trans-stilbene, have been newly identified, and thus providing chemical leads for the further development of anti-inflammatory or cancer chemopreventive agents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.022

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。
• Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor
  作者：Syuhei Nakao、Miyuki Mabuchi、Shenglan Wang、Yoko Kogure、Tadashi Shimizu、Koichi Noguchi、Akito Tanaka、Yi Dai

  DOI：10.1016/j.bmcl.2017.05.025

  日期：2017.7

  A series of 31 resveratrol derivatives was designed, synthesized and evaluated for activation and inhibition of the TRPA1 channel. Most acted as activators and desensitizers of TRPA1 channels like resveratrol or allyl isothiocyanate (AITC). Compound 4z (HUHS029) exhibited higher inhibitory activity than resveratrol with an IC50 value of 16.1 μM. The activity of 4z on TRPA1 was confirmed in TRPA1-expressing

  设计，合成和评估了一系列31种白藜芦醇衍生物，以激活和抑制TRPA1通道。大部分充当白藜芦醇或异硫氰酸烯丙酯（AITC）等TRPA1通道的激活剂和脱敏剂。化合物4z（HUHS029）的抑制活性高于白藜芦醇，IC 50值为16.1μM 。通过全细胞膜片钳记录，在表达TRPA1的HEK293细胞以及大鼠背根神经节神经元中证实了4z对TRPA1的活性。此外，用4z预处理对体内AITC引起的TRPA1相关的疼痛行为表现出镇痛作用。
• An efficient palladium-catalyzed Negishi cross-coupling reaction with arylvinyl iodides: facile regioselective synthesis of E-stilbenes and their analogues
  作者：M. Shahjahan Kabir、Aaron Monte、James M. Cook

  DOI：10.1016/j.tetlet.2007.08.047

  日期：2007.10

  A general synthetic route for the Pd-catalyzed cross-coupling of an arylzinc reagent with arylvinyl iodides (Negishi cross-coupling) has been developed. The system permits efficient and selective preparation of E-stilbenes and their analogues. It also functions effectively at low levels of catalyst loading without the need for an additional ligand and tolerates a wide range of functional groups including

  已经开发出一种通常的合成路线，用于钯催化的芳基锌试剂与芳基乙烯基碘的交叉偶联（Negishi交叉偶联）。该系统允许有效地和选择性地制备E-芪及其类似物。它在催化剂用量低的情况下也能有效发挥功能，而无需其他配体，并能耐受包括杂芳族底物在内的各种官能团。进行了各种参数的系统研究，并将其与催化剂-底物活性相关联。
• [EN] STREPTOCOCCUS MUTANS GLUCOSYL TRANSFERASE INHIBITORS FOR DENTAL CARIES THERAPY<br/>[FR] INHIBITEURS DE GLUCOSYLE TRANSFÉRASE DE STREPTOCOCCUS MUTANS POUR LA THÉRAPIE DES CARIES DENTAIRES
  申请人：UAB RESEARCH FOUNDATION

  公开号：WO2019195430A1

  公开（公告）日：2019-10-10

  The present invention is related to the inhibition of the formation of Streptococci biofilms through the inhibition of glucosyl transferase (Gtf). Compounds, compositions and methods for inhibiting Streptococcus biofilm formation, as well as for preventing, inhibiting and/or treating the formation of dental caries, and methods of identifying compounds that prevent, inhibit and/or treat the formation of dental caries are provided.

  本发明涉及通过抑制葡萄糖基转移酶(Gtf)来抑制链球菌生物膜形成的方法。提供了用于抑制链球菌生物膜形成的化合物、组合物和方法，以及用于预防、抑制和/或治疗龋齿形成的方法，以及用于识别能够预防、抑制和/或治疗龋齿形成的化合物的方法。
• Flavonoids and stilbenes from armand pine
  作者：Jim-Min Fang、Wen-Chiung Su、Yu-Shia Cheng

  DOI：10.1016/0031-9422(88)80201-2

  日期：1988.1

  Abstract Seven flavonoids and seven stilbenes were isolated from the heartwood of Pinus armandii Fr. var. mastersiana Hay. Among them, trans -3,5-dimethoxystilbene oxide is a new compound and 3-acetyloxy-5,7-dihydroxyflavanone is the first report of its occurrence in nature. Comparison of the flavonoid and stilbene components in P. armandii , P. morrisonicola Hay. and P. parviflora Sieb. et Zucc. supports

  摘要 从华山松心材中分离得到七种黄酮类化合物和七种芪。变种 主干草。其中，反式-3,5-二甲氧基二苯乙烯氧化物是一种新化合物，3-乙酰氧基-5,7-二羟基黄烷酮是其在自然界中的首次报道。P. armandii , P. morrisonicola Hay 中类黄酮和芪成分的比较。和 P. parviflora Sieb。等祖克。支持三个物种的化学分类。