(E)-3,4',5-trifluorostilbene

• 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: (E)-3,4',5-trifluorostilbene
• 英文别名: 3,5,4'-trifluorostilbene；(E)-1-(4-fluoroxyphenyl)-2-(3,5-difluorophenyl)-ethene；E-3,5,4'-trifluorostilbene；1,3-difluoro-5-[(E)-2-(4-fluorophenyl)ethenyl]benzene
• 化学式: C₁₄H₉F₃
• 分子量: 234.221
• InChiKey: AISCLLWJTMIDPD-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氟苯乙烯 、 3,5-二氟苯甲酰氯 在 N-乙基吗啉 、 palladium diacetate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 18.0h， 以48%的产率得到(E)-3,4',5-trifluorostilbene
  参考文献：
  名称：

  白藜芦醇氟化类似物的合成，结构表征和生物学评价

  摘要：

  白藜芦醇是一种潜在的化学预防剂，可以从葡萄皮和其他饮食来源中分离出来。Wittig反应和脱羰Heck反应用于合成该二苯乙烯的类似物。合成该二苯乙烯的氟化衍生物，维持3,4'，5-取代模式。羟基也被氨基取代，并评估了生物学活性。在多种细胞系中检测化合物，主要是非小肺癌细胞系DLKP-A。单独或与已知的化学治疗药物表柔比星联用对类似物进行评估。

  DOI：

  10.1016/j.bmc.2009.05.007

文献信息

• Novel Sirtuin Activating Compounds and Methods for Making the Same
  申请人：Andrus Merritt B.

  公开号：US20080255382A1

  公开（公告）日：2008-10-16

  The present invention includes methods for preparing resveratrol, resveratrol esters and substituted and unsubstituted stilbenes of the formula given below; where each Y is —O or halogen, each Z is —O or halogen, each n and each m is independently the value of 0, 1, 2, 3, 4 or 5, each A and each B is independently selected from P n , R or absent, each V and each W is independently selected from P n , straight or branched alkyl of from (2) to (6) carbon atoms and cycloalkyl of from (3) to (8) carbon atoms, alkoxy, phenyl, benzyl or halogen, R is independently selected from the group comprising alkyl with at least one carbon atom, aryl and aralkyl, P n is an alcohol protecting group and diastereoisomers of the foregoing. The compounds are made from a multi-step process including a N-heterocyclic carbon-type ligand coupling in the presence of a base with benzyol halide and styrene coupling partners. These compounds show increased stability for use in the food, cosmetic and pharmaceutical industries.

  本发明涉及一种制备白藜芦醇、白藜芦醇酯和给定以下结构式的取代和未取代的stilbenes的方法；其中每个Y是—O或卤素，每个Z是—O或卤素，每个n和每个m独立地取值为0、1、2、3、4或5，每个A和每个B独立地从Pn、R或缺席中选择，每个V和每个W独立地从Pn、由（2）到（6）个碳原子的直链或支链烷基和由（3）到（8）个碳原子的环烷基、烷氧基、苯基、苄基或卤素中选择，R独立地从包括至少一个碳原子的烷基、芳基和芳基烷基的群体中选择，Pn是醇保护基和上述化合物的对映异构体。这些化合物是通过多步过程制备的，其中包括在碱存在下与苄基卤和苯乙烯偶联合成N-杂环碳型配体偶联。这些化合物在食品、化妆品和制药行业中显示出增强的稳定性。
• NOVEL SIRTUIN ACTIVATING COMPOUNDS AND PROCESSES FOR MAKING THE SAME
  申请人：Andrus Merritt B.

  公开号：US20100185006A1

  公开（公告）日：2010-07-22

  The present invention includes methods for preparing resveratrol, resveratrol esters and substituted and unsubstituted stilbenes of the formula given below; where each Y is —O or halogen, each Z is —O or halogen, each n and each m is independently the value of 0, 1, 2, 3, 4 or 5, each A and each B is independently selected from P n , R or absent, each V and each W is independently selected from P n , straight or branched alkyl of from 2 to 6 carbon atoms and cycloalkyl of from 3 to 8 carbon atoms, alkoxy, phenyl, benzyl or halogen, R is independently selected from the group comprising alkyl with at least one carbon atom, aryl and aralkyl, P n is an alcohol protecting group and diastereoisomers of the foregoing. The compounds are made from a multi-step process including a N-heterocyclic carbene-type ligand coupling in the presence of a base with benzyol halide and styrene coupling partners. These compounds show increased stability for use in the food, cosmetic and pharmaceutical industries.

  本发明涉及制备白藜芦醇、白藜芦醇酯和给出下列式子的取代和未取代的苯乙烯的方法；其中每个Y是—O或卤素，每个Z是—O或卤素，每个n和每个m是独立地取值为0、1、2、3、4或5，每个A和每个B是独立地从Pn、R或缺失中选择，每个V和每个W是独立地从Pn、2到6个碳原子的直链或支链烷基和3到8个碳原子的环烷基、烷氧基、苯基、苄基或卤素中选择，R是独立地从包括至少一个碳原子的烷基、芳基和芳基烷基的群体中选择，Pn是醇保护基和上述化合物的对映异构体。这些化合物是通过多步反应制备的，包括在碱存在下与苯乙烯偶联反应的N-杂环卡宾型配体偶联反应。这些化合物表现出增强的稳定性，可用于食品、化妆品和制药工业中。
• New stilbene derivatives and their use as aryl hydrocarbon receptor ligand antagonists
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP1418164A1

  公开（公告）日：2004-05-12

  The invention relate to stilbene derivatives having formula I wherein R3, R4 and R5 and R3', R4' and R5' are identical or different and represent H, OH, O-alkoxy or hal, said alkoxy group being a C1-C6 alkoxy and "hal" being F, Cl or CF3, with the proviso that one of R4', R3 and R5 or R4, R3' and R5' does not represent OH, OCH3 or OCH2 CH3 when the two other subtituents are both OH, OCH3, OCH2CH3, respectively, and the symmetrical derivatives. Use of said stilbene derivatives particularly as pharmaceutical compositions and food additives.

  本发明涉及具有式 I 的二苯乙烯衍生物 其中 R3、R4 和 R5 以及 R3'、R4'和 R5'相同或不同，代表 H、OH、O-烷氧基或 hal，所述烷氧基为 C1-C6 烷氧基，"hal "为 F、Cl 或 CF3，但 R4'、R3 和 R5 或 R4、R3'和 R5'中的一个不代表 OH、OCH3 或 OCH2CH3，而另外两个副基团分别为 OH、OCH3 或 OCH2CH3、 以及对称衍生物。 所述二苯乙烯衍生物的用途，特别是用作药物组合物和食品添加剂。
• Stilbene derivatives and their use as aryl hydrocarbon receptor antagonistic ligands
  申请人：——

  公开号：US20040147788A1

  公开（公告）日：2004-07-29

  The invention relate to stilbene derivatives having formula I 1 wherein R3, R4 and R5 and R3′, R4′ and R5′ are identical or different and represent H, OH, O-alkoxy or hal, said alkoxy group being a C1-C6 alkoxy and “hal” being F, Cl or CF 3 , with the proviso that one of R4′, R3 and R5 or R4, R3′ and R5′ does not represent OH, OCH 3 or OCH 2 CH 3 when the two other subtituents are both OH, OCH 3 , OCH 2 CH 3 , respectively, and the symmetrical derivatives. Use of said stilbene derivatives particularly as pharmaceutical compositions and food additives.

  本发明涉及具有式 I 的二苯乙烯衍生物 1 其中 R3、R4和R5以及R3′、R4′和R5′相同或不同，代表H、OH、O-烷氧基或hal，所述烷氧基为C1-C6烷氧基，"hal "为F、Cl或CF 3 但 R4′、R3 和 R5 或 R4、R3′和 R5′ 中的一个不代表 OH、OCH 3 或 OCH 2 CH 3 当另外两个副基均为 OH、OCH 3 、OCH 2 CH 3 和对称衍生物、 以及对称衍生物。 上述二苯乙烯衍生物尤其可用作药物成分和食品添加剂。
• Synthesis of polyhydroxylated ester analogs of the stilbene resveratrol using decarbonylative Heck couplings
  作者：Merritt B. Andrus、Jing Liu

  DOI：10.1016/j.tetlet.2006.05.065

  日期：2006.8

  Protected 3,5-hydroxy-benzoyl chlorides 3 were coupled with styrenes 4 to give hydroxylated stilbenes, analogs of resveratrol, an important antioxidant disease preventative agent isolated from grape skins and other dietary sources. Levulinate and chloroacetate protecting groups allowed for the selective production of mono- and di-acetate variations under palladium-N-heterocyclic carbene (NHC) catalyzed decarbonylative coupling conditions. Fluorinated analogs were also produced using Heck conditions with bromofluorobenzenes. Human HL-60 cell assays showed the 4'-acetoxy variant 11 to have improved activity (ED50 17 mu M) relative to resveratrol (24 mu M). (c) 2006 Published by Elsevier Ltd.