(E)-1-(4'-acetoxyphenyl)-2-(3,4-dimethoxyphenyl)ethene | 880354-47-2

• 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)-1-(4'-acetoxyphenyl)-2-(3,4-dimethoxyphenyl)ethene
• 英文别名: (E)-4-(3,4-dimethoxystyryl)phenyl acetate；3,4-dimethoxy-4'-acetoxy-trans-stilbene；3,4-dimethoxy-12-acetoxystilbene；[4-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]phenyl] acetate
• CAS: 880354-47-2
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: KEHLWVZWMAQZKR-SNAWJCMRSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  437.9±35.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(4'-acetoxyphenyl)-2-(3,4-dimethoxyphenyl)ethene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 3,4,4'-trihydroxy-trans-stilbene
  参考文献：
  名称：

  通过TRPA1受体脱敏合成白藜芦醇衍生物作为新的镇痛药

  摘要：

  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。

  DOI：

  10.1016/j.bmcl.2017.05.025
• 作为产物：
  描述：

  3,4-二甲氧基苯乙烯 、 4-碘乙酰基苯酚 在 四丁基溴化铵 、 potassium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到(E)-1-(4'-acetoxyphenyl)-2-(3,4-dimethoxyphenyl)ethene
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer

  摘要：

  A series of new resveratrol analogues were designed and synthesized and their inhibitory activities against aromatase were evaluated. The crystal structure of human aromatase (PDB 3eqm) was used to rationalize the mechanism of action of the aromatase inhibitor 32 (IC50 0.59 mu M) through docking, molecular mechanics energy minimization, and computer graphics molecular modeling, and the information was utilized to design several very potent inhibitors, including compounds 82 (IC50 70 nM) and 84 (IC50 36 nM). The aromatase inhibitory activities of these compounds are much more potent than that for the lead compound resveratrol, which has an IC50 of 80 mu M. In addition to aromatase inhibitory activity, compounds 32 and 44 also displayed potent QR2 inhibitory activity (IC50 1.7 mu M and 0.27 mu M, respectively) and the high-resolution X-ray structures of QR2 in complex with these two compounds provide insight into their mechanism of QR2 inhibition. The aromatase and quinone reductase inhibitors resulting from these studies have potential value in the treatment and prevention of cancer. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.042

文献信息

• Discovery of efficient stimulators for adult hippocampal neurogenesis based on scaffolds in dragon's blood
  作者：Jian-Hua Liang、Liang Yang、Si Wu、Si-Si Liu、Mark Cushman、Jing Tian、Nuo-Min Li、Qing-Hu Yang、He-Ao Zhang、Yun-Jie Qiu、Lin Xiang、Cong-Xuan Ma、Xue-Meng Li、Hong Qing

  DOI：10.1016/j.ejmech.2017.05.025

  日期：2017.8

  discovered to efficiently stimulate adult rats' neurogenesis. In-depth structure-activity relationship studies proved the necessity of a stilbene scaffold that is absent in highly cytotoxic analogs such as chalcones and heteroaryl rings and inactive analogs such as diphenyl acetylene and diphenyl ethane, and validated the importance of an NH in the carboxamide and a methylenedioxy substituent on the

  由衰老和神经系统疾病引起的海马神经发生减少会损害神经回路并导致记忆丧失。一种新的铅化合物（ñ -反式-3'，4'- methylenedioxystilben -4-基乙酰胺27）已发现有效地刺激成年大鼠的神经发生。深入的结构-活性关系研究证明，在高度细胞毒性类似物（如查耳酮和杂芳基环）和无活性类似物（如二苯乙炔和二苯乙烷）中不存在二苯乙烯骨架的必要性，并验证了氨甲酰胺和苯环上的亚甲二氧基取代基。免疫组织化学染色和生化分析表明，与先前报道的神经保护化学物质相比，N-二苯乙烯基羧酰胺具有神经增殖型神经发生的额外能力，从而为提高成年哺乳动物脑的可塑性提供了基础。
• A Simple Access to Biologically Important<i>trans</i>-Stilbenes via Ru-Catalyzed Cross Metathesis
  作者：Hans-Günther Schmalz、Janna Velder、Stefanie Ritter、Johann Lex

  DOI：10.1055/s-2005-918506

  日期：——

  The cross metathesis of methoxy- or acetoxy-substituted styrenes using the Grubbs II catalyst affords unsymmetrical (mixed) E-stilbenes with astonishingly high selectivity (up to 79% yield). This approach offers a short and flexible synthesis of variously substituted stilbenes, which are derivatives or precursors of biologically important compounds such as resveratrol, piceatannol, and pinostilbene

  使用 Grubbs II 催化剂对甲氧基或乙酰氧基取代的苯乙烯进行交叉复分解，得到了具有惊人高选择性（高达 79% 产率）的不对称（混合）E-二苯乙烯。这种方法提供了各种取代的二苯乙烯的短而灵活的合成，它们是生物重要化合物如白藜芦醇、白杉醇和松芪的衍生物或前体。
• METAL-BINDING BIFUNCTIONAL COMPOUNDS AS DIAGNOSTIC AGENTS FOR ALZHEIMER'S DISEASE
  申请人：Washington University

  公开号：US20150209452A1

  公开（公告）日：2015-07-30

  Metal-binding bifunctional compounds and their use as diagnostic agents for Alzheimer's disease and other beta amyloid disorders are disclosed. Also, radiolabeled metal complexes of these bifunctional compounds and their use as positron emission tomography (PET) imaging agents are provided.

  金属结合的双功能化合物及其作为阿尔茨海默病和其他β淀粉样疾病的诊断试剂的使用被披露。此外，还提供了这些双功能化合物的放射性标记金属配合物及其作为正电子发射断层扫描（PET）成像试剂的用途。
• Tandem pericyclic reactions in a new FeCl3-promoted synthesis of catechol analogues of restrytisol C
  作者：N.F Thomas、K.C Lee、Thomas Paraidathathu、J.F.F Weber、K Awang、D Rondeau、P Richomme

  DOI：10.1016/s0040-4020(02)00798-6

  日期：2002.9

  The uncommon stilbene, 3,4-dimethoxy-12-acetoxy stilbene, has been synthesised by Heck coupling methodology in three steps. Treatment of this stilbene with ferric chloride in dichloromethane (room temperature) gave the unnatural stilbenoid dimers; 8,8-(12,12'-bisacetoxyphenyl)-7'-(3',4'-dimethoxyphenyl)-3,4-dimethoxy-7',8'-dihydro-naphthalene and 8-(12-acetoxyphenyl)-8'-(12'-hydroxyphenyl)-7'-(3',4'-diinethoxyphenyl)-3,4-dimethoxy-7',8'-dihydro-naphthalene. The structures of both stilbene dimers were unambiguously confirmed by 1D (H-1, C-13 and 2D NMR experiments (COSY, HMQC, HMBC and NOESY). This is the first report of a FeCl3-promoted sequential pericyclic pathway leading to a highly oxygenated oligostilbenoid dimer (incorporating two asymmetric centres). The NMR spectroscopic evidence and a mechanistic interpretation consistent with these structures are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Heck arylation of styrenes with arenediazonium salts: short, efficient, and stereoselective synthesis of resveratrol, DMU-212, and analogues
  作者：Angélica Venturini Moro、Flávio Sega P. Cardoso、Carlos Roque D. Correia

  DOI：10.1016/j.tetlet.2008.07.087

  日期：2008.9

  Short, efficient, and stereoselective synthesis of the trans-stilbenes resveratrol, DMU-212, and analogues of both compounds are described. The synthesis of these important anti-cancer agents feature the palladium catalyzed Heck-Matsuda arylation of styrenes with arenediazonium tetrafluoroborates. (C) 2008 Elsevier Ltd. All rights reserved.