phenyl 2,2,2-trideuterioacetate | 22705-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: phenyl 2,2,2-trideuterioacetate
• 英文别名: phenyl acetate-d₃；phenyl acetate-d3；2,2,2-trideuterio-acetic acid phenyl ester；<α,α,α-²H(3)>Phenylacetat；Phenyl-；Phenyl-2,2,2-trideuterioacetat
• CAS: 22705-27-7
• 化学式: C₈H₈O₂
• 分子量: 139.126
• InChiKey: IPBVNPXQWQGGJP-FIBGUPNXSA-N

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：

  phenyl 2,2,2-trideuterioacetate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 20.0h， 以5.4%的产率得到乙醇-2,2,2-d3
  参考文献：
  名称：

  吡嗪的研究。第8部分。2-烷氧基吡嗪的热解；取代基效应和立体特异性

  摘要：

  十二个2-烷氧基吡嗪（R = Pr i，Bu s，1,2-二甲基丙基，1,2,2-三甲基丙基，叔丁基，叔戊基，1,1,2-三甲基丙基，1,1,2,2 -四甲基丙基，辛基，新戊基，±-赤-和±-苏-2-（氘-1,2-二苯乙基）已被热解，以阐明取代基对反应速率和立体特异性的影响。确定了列出的前八种化合物的活化参数（log A和E a）。通过α取代促进了反应。这是极性和空间效应的结合。反应的立体特异性很高。

  DOI：

  10.1039/p29840000641
• 作为产物：
  描述：

  乙酰氯-d3 、 苯酚 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 phenyl 2,2,2-trideuterioacetate
  参考文献：
  名称：

  The .beta.-hydrogen secondary isotope effect in acyl transfer reactions. Origins, temperature dependence, and utility as a probe of transition-state structure

  摘要：

  DOI：

  10.1021/ja00526a039

文献信息

• A correlation between .beta.-hydrogen isotope effects on carbon-13 NMR chemical shifts in unsaturated systems and the strength of hyperconjugative interactions
  作者：Cheryl H. Arrowsmith、A. Jerry. Kresge

  DOI：10.1021/ja00285a006

  日期：1986.12

  ..beta..-Hydrogen isotope effects on the carbon-13 NMR chemical shifts of the trigonal carbon in CL/sub 3/C(R)=X (L = H or D) are reported for 15 substances in which the positive charge density at the trigonal carbon is regulated through systematic variation of R and X. A linear relationship is found between these isotope effects and the chemical shifts of the trigonal carbons, and this is taken as

  ..β..-氢同位素对 CL/sub 3/C(R)=X（L = H 或 D）中三角碳的碳 13 NMR 化学位移的影响报告了 15 种物质，其中正电荷三方碳的密度通过 R 和 X 的系统变化来调节。在这些同位素效应和三方碳的化学位移之间发现了线性关系，这被视为这些同位素效应的大小依赖于CL/sub 3/ 和 C(R)=X 之间超共轭相互作用的强度。提出了根据非谐碳氢键弯曲振动对超共轭 NMR 同位素效应的解释。
• Reaction progress at the transition state for nucleophilic attack on esters
  作者：Ildiko M. Kovach、James P. Elrod、Richard L. Schowen

  DOI：10.1021/ja00545a023

  日期：1980.12
• A Uranium(IV) Triamide Species with Brønsted Basic Ligand Character: Metal–Ligand Cooperativity in the f Block
  作者：John J. Kiernicki、Selena L. Staun、Matthias Zeller、Suzanne C. Bart

  DOI：10.1021/acs.organomet.6b00861

  日期：2017.2.13

  Deprotonation of the tridentate triamine ligand H3N3Mes((2,4,6-Me3C6H2N(H)CH2CH2)(2)NH) with 2 equiv of KCH2Ph followed by treatment with 1 equiv of UCl4 afforded the diamidoamine uranium complex (THF)(2)UCl2(HN3Mes) (1-THF). This species was further derivatized with either O=PPh3 or KCp* to generate (Ph3PO)UCI2(HN3Mes) (1-OPPh3) or Cp*UCl(HN3Mes) (2-Cl), respectively. Deprotonation of 2-Cl with "BuLi furnished the uranium(IV) triamido compound Cp*U(N-3(Mes)-LiCl(THF)(2)) (3-LiC1), which is stabilized by the presence of LiCl. 3-LiCl reacts readily with alcohols and thiols, including HOPh, HSPh, and HOtBu, to furnish the respective products Cp*U(OPh)(HN3Mes) (2-OPh), Cp*U(SPh)(FfN(3)(Mes)) (2-SPh), and Cp*U(O'Bu)(HN3Mes) (2-O'Bu); which show cooperative addition of the H-E (E = 0, S) bond across the U-N bond, serving to regenerate the diamidoamine ligand: Similar cooperative addition was noted for 3-LiC1 with benzophenone, furnishing Cp*U(N-3(Mes)-OCPh2) (3-OCPh2), which features new U-O and N-C bonds. The Bronsted basicity of the central nitrogen of 3-LiCI was illustrated by addition of PhOAc, which favored alpha-carbon deprotonation over nucleophilic attack at the carbonyl. All species were subject to a complete spectroscopic and crystallographic analysis, confirming that the reactivity of 3-LiCI in fact involves cooperation from the triamido ligand and uranium center.
• Transition-state structures for ester aminolysis with and without rate-limiting proton transfer
  作者：Ildiko M. Kovach、Michael Belz、Mark Larson、Steven Rousy、Richard L. Schowen

  DOI：10.1021/ja00311a024

  日期：1985.12
• KONAKAHARA, TAKAO;SATO, KENJI;TAKAGI, YUKIO;KUWATA, KAZUHIKO, J. CHEM. SOC. PERKIN TRANS., 1984, N 4, 641-646
  作者：KONAKAHARA, TAKAO、SATO, KENJI、TAKAGI, YUKIO、KUWATA, KAZUHIKO

  DOI：——

  日期：——