methyl 2-phenylacetate-d₂ | 501416-52-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-phenylacetate-d₂
• 英文别名: Methyl 2-Phenylacetate-d2；methyl 2,2-dideuterio-2-phenylacetate
• CAS: 501416-52-0
• 化学式: C₉H₁₀O₂
• 分子量: 152.161
• InChiKey: CRZQGDNQQAALAY-RJSZUWSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl 2-phenylacetate-d₂ 在 lithium aluminium tetrahydride 作用下， 以68%的产率得到2,2-dideuterio-2-phenyl-ethanol
  参考文献：
  名称：

  Dua, Suresh; Adams, Gregory W.; Sheldon, John C., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1996, vol. 6, p. 1251 - 1256

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酸甲酯 在 氘代氯仿 、 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 反应 12.0h， 生成 methyl 2-phenylacetate-d₂
  参考文献：
  名称：

  Triazabicyclodecene:  An Effective Isotope Exchange Catalyst in CDCl₃

  摘要：

  We describe the first effective H/D exchange reaction with acidic substrates in CDCl3 at room temperature. The particularly mild reaction conditions involved (solvent, base, and temperature) allow the chemoselective deuteration of ketones over esters. An NMR study was conducted with the aim of rationalizing the results obtained in the presence of TBD as catalyst.

  DOI：

  10.1021/jo070307h

文献信息

• Copper on charcoal: Cu⁰ nanoparticle catalysed aerobic oxidation of α-diazo esters
  作者：Rong Zhao、Jiangge Teng、Zhiwei Wang、Wenwen Dong、Jia Lin、Changhu Chu

  DOI：10.1039/d1ob00811k

  日期：——

  By using a charcoal supported nano Cu0 catalyst (Cu/C), a highly efficient oxidation of α-diazo esters to α-ketoesters with molecular oxygen as the sole oxidant has been developed. In the presence of the Cu/C catalyst, 2-aryl-α-diazo esters with both electron-donating and electron-withdrawing groups can be oxidized to the corresponding α-ketoesters efficiently. Furthermore, this Cu/C catalyst can catalyse

  通过使用木炭负载纳米Cu 0催化剂（Cu / C），已开发出一种以分子氧为唯一氧化剂将α-重氮酯高效氧化为α-酮酯的方法。在Cu/C催化剂存在下，具有给电子基团和吸电子基团的2-芳基-α-重氮酯可以有效地氧化成相应的α-酮酯。此外，该Cu/C催化剂可以催化芳基α-重氮酯与水反应生成芳基酮酯、2-芳基-2-羟基乙酸酯和2-芳基乙酸酯。在这种情况下，水被α-重氮酯分解，重氮基团被水中的氧或氢原子取代。机理研究表明，α-重氮酯与氧的反应通过自由基途径进行。在 2,2,6,6-四甲基哌啶氮氧化物存在下，α-重氮酯与氧的反应被显着抑制。此外，通过同位素示踪法研究了α-重氮酯与水的反应，GCMS检测表明α-重氮酯与水发生了歧化反应。
• Nitrone/Imine Selectivity Switch in Base‐Catalysed Reaction of Aryl Acetic Acid Esters with Nitrosoarenes: Joint Experimental and Computational Study
  作者：Chiara Volpe、Sara Meninno、Angelo Roselli、Michele Mancinelli、Andrea Mazzanti、Alessandra Lattanzi

  DOI：10.1002/adsc.202000855

  日期：2020.12.8

  2‐diazaphosphorine (BEMP) at room temperature. Depending on the substitution pattern and nature of the aryl moiety, a switch toward the formation of imines can be observed. The mechanistic framework is put to scrutiny by experimental and theoretical studies, pointing to the formation of a nitroso aldol intermediate, whose fate toward one of the competing pathways, namely hydride transfer or elimination

  在此，我们报告了在2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基过氢-1,3，室温下使用2-重氮磷（BEMP）。取决于取代模式和芳基部分的性质，可以观察到向亚胺形成的转换。在机械框架由实验和理论研究投入推敲，指向形成亚硝基羟醛中间体，其命运朝向竞争性途径，即氢化物转移或消除一个，将取决于NOH / CH α相对酸度。
• Visible-Light-Induced Dual C(sp³)–H Bond Functionalization of Tertiary Amine via Hydrogen Transfer to Carbene and Subsequent Cycloaddition
  作者：Kaixiu Luo、Yongqiang Zhao、Zhiliang Tang、Weina Li、Jun Lin、Yi Jin

  DOI：10.1021/acs.orglett.2c02557

  日期：2022.9.2

  we describe the dual C(sp3)–H bond functionalization of a tertiary amine through hydride-transfer-induced dehydrogenation, followed by cycloaddition, using an easily preparable diazoester as a new type hydride-acceptor precursor under mild, redox-neutral conditions. With carbene as a hydrogen acceptor, this method was demonstrated by the preparation of a broad range of functionalized isoxazoldines in

  在此，我们描述了叔胺的双 C(sp 3 )-H 键功能化，通过氢化物转移诱导的脱氢，然后是环加成，使用易于制备的重氮酯作为新型氢化物受体前体，在温和的氧化还原中性下条件。以卡宾为氢受体，该方法通过以中等至高产率制备多种官能化异恶唑烷来证明。
• Resolution of secondary alcohols using 2-acyl-3-phenyl-l-menthopyrazoles as enantioselective acylating agents
  作者：Choji Kashima、Saori Mizuhara、Yohei Miwa、Yukihiro Yokoyama

  DOI：10.1016/s0957-4166(02)00472-x

  日期：2002.8

  The chelation of AlCl3 with N-acylpyrazoles leads to structural fixation of the acyl moiety and an acceleration in the rate of acylation of secondary alcohols. The chiral environment of the fixed acyl moiety of 2-acyl-3-phenyl-1-menthopyrazole 2 causes diastereofacial selectivity in the reaction with secondary alcohols, and thus 2 behaves as an enantioselective acylating agent. By the use of 2.4 molar equivalents of racemic 1-phenylethanol 3a, 2-acetyl-3-phenyl-1-menthopyrazole 2a afforded (S)-1-phenylethyl acetate (S)-4aa enantioselectively and unreacted 3a was recovered with (R)-configuration. Furthermore, the inverse configurational preferences were observed to give (R)-4aa and (S)-3a by the addition of strongly basic amines, which sometimes behaved as catalysts for enolate formation from 2 and AlCl3. These dramatic changes in stereoselective preference should be useful properties of 2-acyl-3-phenyl-1-menthopyrazole 2 as an enantioselective acylating agent. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Adams, Gregory W.; Bowie, John H.; Hayes, Roger N., Journal of the Chemical Society. Perkin transactions II, 1989, p. 2159 - 2168
  作者：Adams, Gregory W.、Bowie, John H.、Hayes, Roger N.

  DOI：——

  日期：——