(E,Z)-α-Acetoxystilbene | 34544-89-3

• 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,Z)-α-Acetoxystilbene
• 英文别名: acetoxystilbene；1,2-Diphenyl-1-acetoxyethen；2-Acetoxy-1.2-diphenyl-aethylen；Desoxybenzoin-enolacetat；Essigsaeure-(1.2-diphenyl-vinylester)；acetic acid stilben-α-yl ester；Essigsaeure-stilben-α-ylester；1-Acetoxy-1.2-diphenyl-aethylen；(1.2-Diphenyl-vinyl)-acetat；α-Acetoxy-stilben；1,2-Diphenyl-2-acetoxyethene；1,2-diphenylethenyl acetate
• CAS: 34544-89-3
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: DUVRDFTXMLOZEC-UHFFFAOYSA-N

物化性质

• 熔点：
  100.5-101.0 °C
• 沸点：
  346.0±31.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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,Z)-α-Acetoxystilbene 在 氢氧化钾 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 18.0h， 以95%的产率得到二苯基乙酮
  参考文献：
  名称：

  Acetoxyselenylation of olefins for the preparation of vinylic and allylic acetates

  摘要：

  DOI：

  10.1021/jo00265a031
• 作为产物：
  描述：

  (1,2-diphenyl-2-phenylselanylethyl) acetate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.25h， 生成 (E,Z)-α-Acetoxystilbene
  参考文献：
  名称：

  Acetoxyselenylation of olefins for the preparation of vinylic and allylic acetates

  摘要：

  DOI：

  10.1021/jo00265a031

文献信息

• Highly efficient Cu(I)-catalyzed trifluoromethylation of aryl(heteroaryl) enol acetates with CF3 radicals derived from CF3SO2Na and TBHP at room temperature
  作者：Yang Lu、Yaming Li、Rong Zhang、Kun Jin、Chunying Duan

  DOI：10.1016/j.jfluchem.2014.01.020

  日期：2014.5

  An efficient method for the Cu(I)-catalyzed synthesis of α-trifluoromethyl ketones via the addition of CF3 to aryl(heteroaryl) enol acetates by using the readily available CF3SO2Na (Langlois reagent) has been developed. The reaction is experimentally simple and carried out at room temperature, providing good to excellent yields with wide functional group tolerance.

  通过加入CF的对α-三氟甲基酮的铜（I）催化合成的有效方法3至芳基通过使用容易获得的CF（杂芳基）乙酸酯烯醇3 SO 2 Na（上兰洛伊斯试剂）已被开发。该反应是简单的实验，并在室温下进行，以优异的产率提供了良好的与宽官能团耐受性。
• Construction of Polysubstituted Olefins through Ni-Catalyzed Direct Activation of Alkenyl CO of Substituted Alkenyl Acetates
  作者：Chang-Liang Sun、Yang Wang、Xiao Zhou、Zhen-Hua Wu、Bi-Jie Li、Bing-Tao Guan、Zhang-Jie Shi

  DOI：10.1002/chem.200902785

  日期：2010.5.25

  Reliable companion: For the first time cross‐coupling between alkenyl acetates and arylboroxines/PhZnCl has been developed via Ni catalysis. Alkenyl acetates could be well‐differentiated from aryl acetates (see scheme). This reliable method provides a convenient pathway to construct polysubstituted styrene derivatives.

  可靠的伴侣：乙酸烯基酯和芳基硼氧烷/ PhZnCl之间的交叉偶联首次通过Ni催化得到了发展。乙酸烯基酯可能与乙酸芳基酯有很好的区别（见方案）。这种可靠的方法为构建多取代的苯乙烯衍生物提供了便利的途径。
• Sulfonation and Trifluoromethylation of Enol Acetates with Sulfonyl Chlorides Using Visible-Light Photoredox Catalysis
  作者：Heng Jiang、Yuanzheng Cheng、Yan Zhang、Shouyun Yu

  DOI：10.1002/ejoc.201300693

  日期：2013.8

  A mild, practical method to prepare α-sulfonyl and α-trifluoromethyl ketones from readily available enol acetates and sulfonyl chlorides has been developed using visible-light photoredox catalysis. The method could be used with a wide range of enol acetates and sulfonyl chlorides, and gave the desired products in satisfactory to excellent yields.

  使用可见光光氧化还原催化，开发了一种从容易获得的烯醇乙酸酯和磺酰氯制备 α-磺酰基和 α-三氟甲基酮的温和、实用的方法。该方法可用于广泛的烯醇乙酸酯和磺酰氯，并以令人满意的收率得到所需的产品。
• Metal-free synthesis of ketonitriles <i>via</i> C–F bond cleavage
  作者：Ge Gao、Zhiping Li

  DOI：10.1039/d2nj06338g

  日期：——

  β-Ketonitriles are an important class of compounds in organic synthesis. A new and practical cyanation of α-CF3 carbonyls with aqueous ammonia is developed. A broad spectrum of α-CF3 carbonyls, including ketones, amides and esters, could be converted to the corresponding β-ketonitriles under mild conditions. The present cyanation uses easily available materials and avoids the use of toxic cyanating

  β-酮腈是有机合成中一类重要的化合物。开发了一种新型实用的α-CF 3羰基与氨水的氰化反应。广谱的 α-CF 3羰基化合物，包括酮、酰胺和酯，可以在温和条件下转化为相应的 β-酮腈。本氰化使用容易获得的材料并且避免使用有毒的氰化试剂。
• Hydration of alkynes in anhydrous medium with formic acid as water donor
  作者：Naim Menashe、Youval Shvo

  DOI：10.1021/jo00078a023

  日期：1993.12

  Formic acid has been found to hydrate alkynes in the absence of water to give oxo products and carbon monoxide. The scope of the reaction of alkynes and formic acid has been delineated. Hydrocarbon alkynes were found to be reactive in the absence of catalyst. Functionalized alkynes, in particular oxygenated alkynes, are inert toward formic acid but can be activated catalytically with Ru3(CO)12. Consequently, all the tested types of alkynes were found to give oxo products and CO with formic acid. The mechanism of the reaction was examined. With some alkynes, the primary oxo products underwent secondary reactions that gave rise to unexpected products.