(E)-3-乙酰氧基芪 | 34701-61-6

• 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-乙酰氧基芪
• 英文名称: (E)-3-styrylphenyl acetate
• 英文别名: trans-1-(m-Acetoxyphenyl)-2-phenylethen；(E)-3-acetoxystilbene；3,4',5-Acetoxystilbene；[3-[(E)-2-phenylethenyl]phenyl] acetate
• CAS: 34701-61-6
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: OSARGCDKCQLKAG-ZHACJKMWSA-N

物化性质

• 沸点：
  371.6±22.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-乙酰氧基芪 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 (E)-3-styrylphenyl 3,4,5-tris((tert-butyldimethylsilyl)oxy)benzoate
  参考文献：
  名称：

  Galloyl esters of trans-stilbenes are inhibitors of FASN with anticancer activity on non-small cell lung cancer cells

  摘要：

  Fatty acid synthase (FASN) is a lipogenic enzyme that is selectively upregulated in malignant cells. There is growing consensus on the oncogenicity of FASN-driven lipogenesis and the potential of FASN as a druggable target in cancer. Here, we report the synthesis and FASN inhibitory activities of two novel galloyl esters of trans-stilbene EC1 and EC5. Inhibition of FASN was accompanied by a loss in AKT activation and profound apoptosis in several non-small cell lung cancer (NSCLC) cells at the growth inhibitory concentrations of EC1 and EC5. Both FASN and phospho-AKT levels were concurrently downregulated. However, addition of a lipid concentrate to the treated cells reinstated cell viability and reversed the loss of FASN and AKT protein levels, thus recapitulating the causal relationship between FASN inhibition and the loss in cell viability. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111597
• 作为产物：
  描述：

  4-碘苯酚 在 4-二甲氨基吡啶 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 (E)-3-乙酰氧基芪
  参考文献：
  名称：

  Galloyl esters of trans-stilbenes are inhibitors of FASN with anticancer activity on non-small cell lung cancer cells

  摘要：

  Fatty acid synthase (FASN) is a lipogenic enzyme that is selectively upregulated in malignant cells. There is growing consensus on the oncogenicity of FASN-driven lipogenesis and the potential of FASN as a druggable target in cancer. Here, we report the synthesis and FASN inhibitory activities of two novel galloyl esters of trans-stilbene EC1 and EC5. Inhibition of FASN was accompanied by a loss in AKT activation and profound apoptosis in several non-small cell lung cancer (NSCLC) cells at the growth inhibitory concentrations of EC1 and EC5. Both FASN and phospho-AKT levels were concurrently downregulated. However, addition of a lipid concentrate to the treated cells reinstated cell viability and reversed the loss of FASN and AKT protein levels, thus recapitulating the causal relationship between FASN inhibition and the loss in cell viability. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111597

文献信息

• Room-Temperature <i>meta</i>-Functionalization: Pd(II)-Catalyzed Synthesis of 1,3,5-Trialkenyl Arene and <i>meta</i>-Hydroxylated Olefin
  作者：Milan Bera、Santosh K. Sahoo、Debabrata Maiti

  DOI：10.1021/acscatal.6b00675

  日期：2016.6.3

  reactions at room temperature continues to be a tough challenge. Use of a phosphonate linkage allowed a Pd (II)-catalyzed meta-C–H functionalization at room temperature while incorporating a cyanophenol-based directing moiety. Successful implementation of sequential di-meta-olefination led to the synthesis of a trialkenyl arene, which has applications in organic electronics and optoelectronics. Under robust

  在室温下发展间位-C-H官能化反应仍然是一个艰巨的挑战。膦酸酯键的使用允许Pd（II）在室温下催化间位C–H官能化，同时引入基于氰基酚的导向部分。顺序二元间烯烃的成功实施导致了三烯基芳烃的合成，该三烯基芳烃已在有机电子学和光电子学中得到应用。在稳定的条件下，已经发现了C-O键形成的间位羟基化和间位乙酰氧基化。
• MOLECULARLY IMPRINTED POLYMERS
  申请人：Hearn Milton T. W.

  公开号：US20120052757A1

  公开（公告）日：2012-03-01

  The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.

  本发明提供了设计分子印迹聚合物（MIPs）的方法，这些方法在从各种生物加工原料和废弃物中提取生物活性化合物方面具有应用。本发明进一步针对由本发明方法设计的MIPs。
• Pd-Catalyzed Decarbonylative Heck Olefination of Aromatic Carboxylic Acids Activated in situ with Di-<i>tert</i>-butyl Dicarbonate
  作者：Lukas J. Gooßen、Jens Paetzold、Lars Winkel

  DOI：10.1055/s-2002-34227

  日期：——

  The first protocol for a direct Heck olefination of aroma­tic carboxylic acids has been developed. By treatment with commercially available di-tert-butyl dicarbonate, the carboxylic acids are converted in situ into the mixed anhydrides, which in the presence of a palladium catalyst react with olefins to give styrene derivatives. As by-products, only volatile CO and CO2 along with tert-butanol are formed, making the work-up of the reaction products particuarly easy. A mixture of PdCl2, LiCl and γ-picoline was identified to be the most effective catalyst system.

  已经开发出一种直接的芳香族羧酸Heck烯化的首个协议。通过与商业可得的二叔丁基二碳酸酯处理，羧酸在原位转化为混合酸酐，在钯催化剂的存在下与烯烃反应，生成苯乙烯衍生物。作为副产物，仅生成挥发性的CO和CO2以及叔丁醇，使反应产物的后处理特别简单。 PdCl2、LiCl和γ-吡啶的混合物被确定为最有效的催化剂体系。
• Prenylated hydroxystilbenes
  申请人：Duke Colin Charles

  公开号：US10196335B2

  公开（公告）日：2019-02-05

  Prenylated stilbene compounds and the use of such compounds in the treatment of diseases and medical disorders, for example cancer, skin ageing, inflammation, bacterial or fungal infection and immunosuppression.

  异戊烯基二苯乙烯化合物，以及将此类化合物用于治疗疾病和医学紊乱，例如癌症、皮肤老化、炎症、细菌或真菌感染以及免疫抑制。
• Decarbonylative Heck Olefination of Enol Esters: Salt-Free and Environmentally Friendly Access to Vinyl Arenes
  作者：Lukas J. Gooßen、Jens Paetzold

  DOI：10.1002/anie.200352357

  日期：2004.2.20