(2-苯基苯基)乙酸酯 | 3271-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2-苯基苯基)乙酸酯
• 英文名称: 2-acetoxybiphenyl
• 英文别名: o-acetoxybiphenyl；(2-phenylphenyl) acetate
• CAS: 3271-80-5
• 化学式: C₁₄H₁₂O₂
• mdl: MFCD00447698
• 分子量: 212.248
• InChiKey: UZUGIHHGLRFGMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  63-63.5 °C
• 沸点：
  139-141 °C(Press: 1 Torr)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  (2-苯基苯基)乙酸酯 在 aluminum (III) chloride 作用下， 以 邻二氯苯 为溶剂， 反应 24.0h， 以64%的产率得到1-(2-羟基联苯-3-基)乙酮
  参考文献：
  名称：

  从头合成三环5,5-苯环螺缩酮

  摘要：

  三环5,5-苯基环化的螺缩酮骨架的合成从2'-羟基苯乙完成和宝石-dibromoalkenes涉及一釜骨牌策略。迄今未知的转化以高收率和广泛的底物范围提供了三环5,5-苯甲酰化螺环酮，为单一非对映异构体。

  DOI：

  10.1021/acs.orglett.1c01109
• 作为产物：
  描述：

  (2E,4e)-5-苯基-2,4-戊二烯酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 苯 为溶剂， -30.0~140.0 ℃ 、5.07 MPa 条件下， 反应 8.0h， 生成 (2-苯基苯基)乙酸酯
  参考文献：
  名称：

  Novel synthesis of phenol derivatives by palladium-catalyzed cyclocarbonylation of 2,4-pentadienyl acetates

  摘要：

  Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140-degrees-C under 50 atm of CO. No five-membered ring products were observed. A platinum complex PtCl2(PPh3)2 was also effective as a catalyst. The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3, 5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51% yield on heating to 160-degrees-C under 50 atm of CO in the presence of NEt3 and Ac2O. Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates. On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)-benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO molecules, respectively.

  DOI：

  10.1021/jo00076a051

文献信息

• Rice husk: Introduction of a green, cheap and reusable catalyst for the protection of alcohols, phenols, amines and thiols
  作者：Farhad Shirini、Somayeh Akbari-Dadamahaleh、Ali Mohammad-Khah、Ali-Reza Aliakbar

  DOI：10.1016/j.crci.2013.01.018

  日期：2014.2

  eco-friendly protocol for the chemoselective protection of benzylic and primary and less hindered secondary aliphatic alcohols and phenols as trimethylsilyl ethers and different types of amines as N-tert-butylcarbamates is developed using rice husk (RiH) as the catalyst. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols and amines with acetic anhydride. Easy work-up, relatively

  摘要 以稻壳 (RiH) 为原料，开发了一种温和、高效、环保的方案，用于化学选择性保护苄基和伯和受阻较小的仲脂肪醇和酚作为三甲基甲硅烷基醚以及不同类型的胺作为 N-叔丁基氨基甲酸酯。催化剂。该试剂还能够催化醇、酚、硫醇和胺与乙酸酐的乙酰化反应。该方法的显着特点是后处理简单、反应时间相对较短、收率高、成本低、催化剂的可用性和可重复使用性是该方法的显着特点，可被认为是保护醇、酚的最佳和通用方法之一、硫醇和胺。此外，
• Formation and reactivity of 1,3-benzodioxol-2-yl, 1,3-benzodioxan-2-yl, and related radicals. A search for an aromatic analog of the radical acetoxy rearrangement (Surzur–Tanner reaction)
  作者：Fereidoon Shahidi、Thomas T. Tidwell

  DOI：10.1139/v82-162

  日期：1982.5.1

  Reaction of the 1,3-dioxole, 9, the 1,3-dioxan, 18, and the 1,3-dioxepin, 29, with tert-butoxy radicals gave evidence in each case for formation of the corresponding 1,1-dioxyethyl radicals. No conclusive evidence for formation of any of these radicals by cyclization of acetoxyaryl radicals could be obtained. Several of the 1,1-dioxyethyl radicals reacted by rearrangement.

  1,3-二氧杂环戊烷（9）、1,3-二氧杂环己烷（18）和1,3-二氧杂环庚烷（29）与叔丁氧基自由基反应，在每种情况下都证明了相应1,1-二氧乙基自由基的形成。没有获得任何这些自由基是通过乙酰氧基芳基自由基环化形成的结论性证据。其中几种1,1-二氧乙基自由基通过重排反应。

• Rice Husk Ash: A New, Cheap, Efficient, and Reusable Reagent for the Protection of Alcohols, Phenols, Amines, and Thiols
  作者：F. Shirini、Somayeh Akbari-Dadamahaleh、Ali Mohammad-Khah

  DOI：10.1080/10426507.2013.844142

  日期：2014.5.4

  Abstract A mild, efficient, and eco-friendly protocol for the protection of alcohols and phenols as trimethylsilyl ethers has been developed using rice husk ash as a reagent. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols, and amines with acetic anhydride. All reactions were performed under mild conditions in good to high yields. [Supplementary materials are available

  摘要 以稻壳灰为试剂，开发了一种温和、高效、环保的三甲基甲硅烷基醚类醇类和酚类保护方案。该试剂还能够催化醇、酚、硫醇和胺与乙酸酐的乙酰化反应。所有反应均在温和条件下以良好至高产率进行。[本文提供补充材料。访问出版商的在线版磷、硫和硅及相关元素，获取以下免费补充文件：附加文本、表格和数字。] 图形摘要
• Polymer-Supported Palladium(II) Carbene Complexes: Catalytic Activity, Recyclability, and Selectivity in C−H Acetoxylation of Arenes
  作者：Maitham H. Majeed、Payam Shayesteh、L. Reine Wallenberg、Axel R. Persson、Niclas Johansson、Lei Ye、Joachim Schnadt、Ola F. Wendt

  DOI：10.1002/chem.201700777

  日期：2017.6.22

  naphthalene compared to the best homogeneous catalysts. The new polymer-supported catalysts maintain the original oxidation state of PdII after repeated catalytic reactions, and exhibit no significant leaching of palladium. In addition, the new catalysts have been successfully recovered and reused without loss of activity over several cycles of reactions.

  通过新型N-杂环卡宾-钯（II）（NHC-Pd II）单体与二乙烯基苯的共聚反应，合成了用于CH键选择性氧化的非均相催化剂。聚合物支持的NHC-Pd II催化的简单和甲基化的芳烃以及聚芳烃的无方向C-H乙酰氧基化，与它们的均相类似物相比具有相似或更高的效率。特别地，与最佳均相催化剂相比，联苯和萘的乙酰氧基化反应的区域选择性得到了改善。新的聚合物负载型催化剂保持了Pd II的原始氧化态经过反复的催化反应，并没有显示出明显的钯浸出。此外，新催化剂已经成功回收并重复使用，并且在多个反应循环中都没有损失活性。
• Aryne cycloaddition reactions of benzodioxasilines as aryne precursors generated by catalytic reductive ortho-C H silylation of phenols with traceless acetal directing groups
  作者：Parham Asgari、Udaya Sree Dakarapu、Hiep H. Nguyen、Junha Jeon

  DOI：10.1016/j.tet.2016.12.002

  日期：2017.7

  Diversely substituted arylsilyl triflates, as aryne precursors for aryne cycloaddition reactions, were accessed from benzodioxasilines. Catalytic reductive C-H ortho-silylation of phenols with traceless acetal directing groups was exploited to prepare benzodioxasilines. Sequential addition of MeLi and then trifluoromethanesulfonic anhydride to benzodioxasilines provided arylsilyl triflates in a single

  多取代的芳基甲硅烷基三氟甲磺酸酯作为芳基环加成反应的芳基前体，是从苯并二氧杂硅烷中获得的。利用无痕缩醛导向基团对苯酚进行催化还原 CH 邻位硅烷化反应来制备苯并二氧杂硅烷。将MeLi、然后三氟甲磺酸酐依次添加至苯并二恶硅烷中，在单锅中提供芳基甲硅烷基三氟甲磺酸酯。值得注意的是，该方法成功地用于制备空间位阻的1,2,3-三取代芳基甲硅烷基三氟甲磺酸酯，并最终进行氟化物介导的芳基环加成。