(Z)-1-Acetoxy-2-(p-anisyl)ethene | 37973-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-1-Acetoxy-2-(p-anisyl)ethene
• 英文别名: (Z)-p-Methoxystyryl Acetate；(Z)-4-methoxystyryl acetate；[(Z)-2-(4-methoxyphenyl)ethenyl] acetate
• CAS: 37973-48-1
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: SPPXZWIFOATPRB-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 臭氧 作用下， 生成 (Z)-1-Acetoxy-2-(p-anisyl)ethene 、 (E)-1-Acetoxy-2-(p-anisyl)ethene
  参考文献：
  名称：

  Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone

  摘要：

  Ozonolysis of N-(arylidene(or alkylidene)amino)-2-azetidinones followed by NaBH4 workup yields enol ethers in good yields with high levels of stereoselectivity. Di- and trisubstituted olefin derivatives are available through this procedure. Chiral 2-azetidinones lead to enol ethers with a chiral moiety without racemization. The reaction is thought to occur through a novel B-type fragmentation of the 2-azetidinone ring. This process is closely related to the well-known N-nitrosoamide to ester rearrangement and the decarboxylation of oxetan-2-ones.

  DOI：

  10.1021/jo00124a008

文献信息

• Stereoselective Synthesis of Vinylboronates by Rh‐Catalyzed Borylation of Stereoisomeric Mixtures
  作者：Shenhuan Li、Jie Li、Tianlai Xia、Wanxiang Zhao

  DOI：10.1002/cjoc.201800575

  日期：2019.5

  The stereoselective preparation of vinylboronates via rhodium‐catalyzed borylation of E/Z mixtures of vinyl actetates is described, and this method was also extended to synthesis of vinyldiboronates. These transformations feature high functional group compatibility and mild reaction conditions. Control experiments support a mechanism that involved a Rh‐catalyzed borylation‐isomerization sequence. The

  描述了通过铑催化的乙酸乙烯酯的E / Z混合物的硼酸化硼酸立体选择性地制备乙烯基硼酸酯的方法，该方法还扩展到乙烯基二硼酸酯的合成。这些转变具有高官能团相容性和温和的反应条件。对照实验支持一种涉及Rh催化的硼酸酯化异构化序列的机制。还证明了（Z）-乙烯基硼酸酯的异构化为（E）-异构体。
• Carboxylic acid addition to terminal alkynes utilizing ammonium tagged Hoveyda-Grubbs catalyst supported on magnetically separable core/shell silica: A highly reusable and air compatible catalytic system
  作者：Bengi Özgün Öztürk、Didar Gürcü、Solmaz Karabulut Şehitoğlu

  DOI：10.1016/j.jorganchem.2019.01.005

  日期：2019.3

  core/shell silica gel was tested on carboxylic acid addition reactions to terminal alkynes using a variety of carboxylic acid derivatives under air atmosphere. The catalytic system was found to be compatible with air atmosphere and can tolerate even non-degassed solvents. The reaction parameters such as temperature, substrate/catalyst ratio and the effect of carboxylic acid on the selectivity and yield of

  在这项研究中，在空气气氛下，使用多种羧酸衍生物，在可磁分离的核/壳硅胶上负载有铵盐的Hoveyda-Grubbs催化剂，对羧酸加成至末端炔烃的反应进行了测试。发现该催化体系与大气兼容，甚至可以耐受非脱气溶剂。详细研究了反应参数，如温度，底物/催化剂比以及羧酸对反应的选择性和收率的影响。芳基乙炔与乙酸的反应生成相应的E-异构体，其转化率高达99％，催化负载率为1％Ru。在空气气氛下，使用乙酸/苯甲酸和苯乙炔在甲苯中的甲苯，在85°C下测试了催化剂的可重复使用性。
• Palladium catalysed β-selective oxidative Heck reaction of an electron-rich olefin
  作者：Lingkui Meng、Chao Liu、Wei Zhang、Chao Zhou、Aiwen Lei

  DOI：10.1039/c3cc47045h

  日期：——

  A palladium catalysed oxidative beta-arylation of an electron-rich olefin is described. The reaction was under mild conditions; meanwhile, additives and directing groups are not needed. Various arylboronic acids worked well under the standard conditions.

  描述了富电子烯烃的钯催化的氧化β-芳基化。反应在温和的条件下进行。同时，不需要添加剂和导向基团。各种芳基硼酸在标准条件下效果很好。
• Heck,R.F., Organometallics in Chemical Synthesis, 1972, vol. 1, p. 455 - 462
  作者：Heck,R.F.

  DOI：——

  日期：——