苯基乙酸酯-d5 | 22705-26-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 苯基乙酸酯-d5
• 中文别名: 乙酸苯酯-d5
• 英文名称: pentadeuterophenylacetate
• 英文别名: [D5]phenyl acetate；acetic acid pentadeuteriophenyl ester；-acetat；(2,3,4,5,6-Pentadeuteriophenyl) acetate
• CAS: 22705-26-6
• 化学式: C₈H₈O₂
• 分子量: 141.111
• InChiKey: IPBVNPXQWQGGJP-VIQYUKPQSA-N

物化性质

• 溶解度：
  氯仿（少量溶解）、DMSO（少量溶解）、乙酸乙酯（少量溶解）、甲醇（少量溶解）

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  苯基乙酸酯-d5 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 ortho-hydroxyacetophenone-d4
  参考文献：
  名称：

  Semi-empirical and vibrational studies of flavone and some deuterated analogues

  摘要：

  The infrared solid state, Raman solid state and tetrachloride solution spectra of flavone have been obtained. Assignments of most of the vibrational data have been performed by comparison between the spectra of flavone and three isotopic species, deuterated on the A, B and C rings, respectively. The vibrational frequencies for all the investigated compounds have been calculated from the conformational analysis of flavone using the semi-empirical AM1 method and compared with experimental values. The correlation is more or less satisfactory; however, for some vibrational modes, the calculated isotopic shifts agree better with experiment than do the frequencies themselves, Specific vibrational modes which retain a benzene ring monosubstituted and ortho-distributed character have been recognized in the spectra, according to literature data, isotopic frequency shifts and graphic representation of the atomic displacements.

  DOI：

  10.1016/0584-8539(93)e0033-s
• 作为产物：
  描述：

  氘代苯 、 乙酸酐 在 碘苯二乙酸 、 palladium diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 3.02h， 以10.47%的产率得到苯基乙酸酯-d5
  参考文献：
  名称：

  Pd（OAc）2 /吡啶催化剂的反应性极高：非定向C ？芳烃的H氧合

  摘要：

  少即是多：描述了催化体系Pd（OAc）2 /吡啶的合理优化和一般适用性（请参阅方案）。该催化剂在简单的芳香族底物的CH氧化反应中显示出极好的反应性。Pd /吡啶比是至关重要的，因为与单独的Pd（OAc）2相比，每个Pd中心使用一当量的吡啶会导致反应性和位点选择性的显着提高。

  DOI：

  10.1002/anie.201103327

文献信息

• Silver-Catalyzed Functionalization of Esters by Carbene Transfer: The Role of Ylide Zwitterionic Intermediates
  作者：Riccardo Gava、M. Ángeles Fuentes、Maria Besora、Tomás R. Belderrain、Kane Jacob、Feliu Maseras、Michel Etienne、Ana Caballero、Pedro J. Pérez

  DOI：10.1002/cctc.201402241

  日期：2014.8

  The reaction of esters with ethyl diazoacetate catalyzed by the complex [F27–TpAg(acetone)] generates α‐(acyloxy)acetates in moderate to high yields. This is a novel transformation in the context of carbene‐transfer reactions from diazo compounds that, according to experimental and theoretical data, is suggested to occur through zwitterionic intermediates.

  络合物[F 27 -Tp Ag（丙酮）]催化的酯类与重氮乙酸乙酯反应生成α-（酰氧基）乙酸酯，产率中等至高。在重氮化合物进行卡宾转移反应的背景下，这是一种新颖的转变，根据实验和理论数据，该转变建议通过两性离子中间体发生。
• Mechanism of the Palladium-Catalyzed Arene C–H Acetoxylation: A Comparison of Catalysts and Ligand Effects
  作者：Amanda K. Cook、Melanie S. Sanford

  DOI：10.1021/jacs.5b00238

  日期：2015.3.4

  This article describes detailed mechanistic studies focused on elucidating the impact of pyridine ligands on the Pd-catalyzed C-H acetoxylation of benzene. Three different catalysts, Pd(OAc)2, Pd(OAc)2/pyridine (1:1), and Pd(OAc)2/pyridine (1:2), are compared using a combination of mechanistic tools, including rate and order studies, Hammett analysis, detailed characterization of catalyst resting states

  本文介绍了详细的机理研究，重点是阐明吡啶配体对 Pd 催化的苯的 CH 乙酰氧基化的影响。三种不同的催化剂，Pd(OAc)2、Pd(OAc)2/吡啶 (1:1) 和 Pd(OAc)2/吡啶 (1:2)，使用包括速率和顺序在内的机械工具的组合进行比较研究、哈米特分析、催化剂静止状态的详细表征和同位素效应。这些实验的数据表明 CH 激活是所有情况下的限速步骤。三种催化剂之间的主要区别被认为是 Pd 的静止状态。在反应条件下，Pd(OAc)2 以乙酸酯桥接二聚体形式存在，而 Pd(OAc)2/吡啶 (1:2) 催化剂以单体 (吡啶)2Pd(OAc)2 形式存在。相比之下，
• COUCH, M. W.;GABRIELSEN, B. M.;MIDGLEY, J. M., J. LABELLED COMPOUNDS AND RADIOPHARM., 1983, 20, N 8, 933-949
  作者：COUCH, M. W.、GABRIELSEN, B. M.、MIDGLEY, J. M.

  DOI：——

  日期：——
• Remarkably High Reactivity of Pd(OAc)2/Pyridine Catalysts: Nondirected CH Oxygenation of Arenes
  作者：Marion H. Emmert、Amanda K. Cook、Yushu J. Xie、Melanie S. Sanford

  DOI：10.1002/anie.201103327

  日期：2011.9.26

  general applicability of the catalytic system Pd(OAc)2/pyridine is described (see scheme). The catalyst shows excellent reactivity in the CH oxygenation of simple aromatic substrates. The Pd/pyridine ratio is critical as the use of one equivalent of pyridine per Pd center leads to dramatic enhancements in both reactivity and site selectivity in comparison to Pd(OAc)2 alone.

  少即是多：描述了催化体系Pd（OAc）2 /吡啶的合理优化和一般适用性（请参阅方案）。该催化剂在简单的芳香族底物的CH氧化反应中显示出极好的反应性。Pd /吡啶比是至关重要的，因为与单独的Pd（OAc）2相比，每个Pd中心使用一当量的吡啶会导致反应性和位点选择性的显着提高。
• Semi-empirical and vibrational studies of flavone and some deuterated analogues
  作者：L. Vrielynck、J.P. Cornard、J.C. Merlin、M.F. Lautie

  DOI：10.1016/0584-8539(93)e0033-s

  日期：1994.11

  The infrared solid state, Raman solid state and tetrachloride solution spectra of flavone have been obtained. Assignments of most of the vibrational data have been performed by comparison between the spectra of flavone and three isotopic species, deuterated on the A, B and C rings, respectively. The vibrational frequencies for all the investigated compounds have been calculated from the conformational analysis of flavone using the semi-empirical AM1 method and compared with experimental values. The correlation is more or less satisfactory; however, for some vibrational modes, the calculated isotopic shifts agree better with experiment than do the frequencies themselves, Specific vibrational modes which retain a benzene ring monosubstituted and ortho-distributed character have been recognized in the spectra, according to literature data, isotopic frequency shifts and graphic representation of the atomic displacements.