3,3-dideutero-3-phenylpropionic acid | 23094-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3-dideutero-3-phenylpropionic acid
• 英文别名: 3,3-dideuterio-3-phenyl-propionic acid；Hydrocinnamic-β,β-d(2)-acid；3,3-Dideutero-hydrozimtsaeure
• CAS: 23094-22-6
• 化学式: C₉H₁₀O₂
• 分子量: 152.161
• InChiKey: XMIIGOLPHOKFCH-NCYHJHSESA-N

物化性质

• 熔点：
  46-48 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3,3-dideutero-3-phenylpropionic acid 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-phenyl-N-(quinolin-8-yl)propanamide-3,3-D₂
  参考文献：
  名称：

  配体辅助的钯（II）/（IV）氧化sp3 C吗？H氟化

  摘要：

  的惰性的直接官能SP 3个Ç  H键被限制到几个键的类型。虽然活化SP 3 Ç H键可以使用钯催化剂在温和的条件下完成，由于将钯（II）转化为钯（IV）需要高能量，因此随后的官能化并非无关紧要。我们已经使用计算指导性实验系统地研究了钯的氧化，以进行涉及强螯合控制的反应。我们发现，温和的外部配体可以显着加速强二齿导向基团的钯（II）氧化为钯（IV）。认为该加速是钯（II）和钯（IV）中间体的配体稳定化的结果。

  DOI：

  10.1002/adsc.201600015
• 作为产物：
  描述：

  2,2-d₂-phenethyl bromide 在 magnesium 作用下， 生成 3,3-dideutero-3-phenylpropionic acid
  参考文献：
  名称：

  On the generation and characterization of the spiro[2,5]octadienyl anion in the gas phase

  摘要：

  AbstractThree routes have been explored in both a high‐pressure chemical ionization (CI) source and a low‐pressure Fourier transform ion cyclotron resonance (FT‐ICR) cell to generate the spiro[2,5]octadienyl anion in the gas phase: (i) proton abstraction from spiro[2,5]octa‐4,6‐diene; (ii) expulsion of trimethysilyl fluoride by phenyl ring participation following fluoride anion attack upon the silicon centre of 2‐phenylethyl trimethylsilane; and (iii) collisionally induced dissociation (CID) of the carboxylate anion of 3‐phenylpropanoic acid via carbon dioxide loss. From comparison of the CID spectra of various reference [C8H9]− ions with those of the [C8H9]− ions which could be generated via the routes (i) and (iii) in the CI source it can be concluded that only the third route yields a [C8H9]−ion whose CID spectrum is not inconsistent with the one expected for the spiro[2,5]octadienyl anion. In the FT‐ICR cell [C8H9]− ions are generated along all three routes; their structures have been identified by specific ion‐molecule reactions and appear to be different. Route (i) yields an α‐methyl benzyl anion, probably due to isomerization within the ion‐molecule complex formed. An ortho‐ethylphenyl anion is formed along route (ii), presumably due to an intramolecular ortho proton abstraction in the generated trimethylsilyl fluoride solvated 2‐phenylethyl primary carbanion. The [C8H9]− ion formed along route (iii) shows reactions similar to those of the 1,1‐dimethylcyclohexadienyl anion which is structurally related to the spiro[2,5]octadienyl anion. Furthermore, the [C8H9]− ion generated via route (iii) reacts with hexafluorobenzene under expulsion of only one hydrogen fluoride molecule which contains exclusively one of the original phenyl ring hydrogen atoms. On the basis of all these observations it is therefore quite likely that the spiro[2,5]octadienyl anion is formed by collisionally induced decarboxylation of the 3‐phenylpropanoic acid carboxylate anion and can be a long‐lived and stable species in the gas phase.

  DOI：

  10.1002/oms.1210240807

文献信息

• Iron-Catalyzed α,β-Dehydrogenation of Carbonyl Compounds
  作者：Xiao-Wei Zhang、Guo-Qing Jiang、Shu-Hui Lei、Xiang-Huan Shan、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.orglett.1c00043

  日期：2021.3.5

  An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.

  开发了铁催化羰基化合物的α，β-脱氢反应。广谱的羰基化合物或类似物，例如醛，酮，内酯，内酰胺，胺和醇，可通过简单的一步反应以高收率转化为它们的α，β-不饱和对应物。
• Diagnostic fragmentations of adducts formed between carbanions and carbon disulfide in the gas phase. A joint experimental and theoretical study
  作者：Micheal J. Maclean、Scott Walker、Tianfang Wang、Peter C. H. Eichinger、Patrick J. Sherman、John H. Bowie

  DOI：10.1039/b916477d

  日期：——

  react with carbon disulfide in a modified LCQ ion trap mass spectrometer to form adducts, which when collisionally activated, decompose by processes which in some cases identify the structures of the original carbanions. For example (i) C6H5− + CS2→ C6H5CS2−→ C6H5S− + CS, occurs through a 3-membered ring ipso transition state, and (ii) the reaction between C6H5CH2− and CS2 gives an adduct which loses

  选定的碳负离子会与 二硫化碳 在修改后 立法会离子阱质谱仪形成加合物，当被碰撞活化时，加合物会通过某些过程分解，该过程在某些情况下可识别原始碳负离子的结构。例如（ⅰ）C 6 H ^ 5 - + CS 2 →C 6 H ^ 5 CS 2 - →C 6 H ^ 5小号- + CS，发生通过一个3元环本位过渡状态，以及（ii）C之间的反应6 ħ 5 CH 2 -和CS 2给出了失去H成加合物2 S，而之间形成的加合物（S）ø-CH 3 Ç 6 ħ 5 -和CS 2失去ħ 2 S和CS。最后，它表明的C脱羧6 ħ 5 CH 2 CH 2 CO 2 -产生β苯乙基阴离子（的PhCH 2 CH 2 - ），以及与CS此热能化阴离子反应2形成C 6 ħ 5 CH 2 CH 2 CS 2 -其在通电时通过处理C片段特异性6 ħ 5CH 2 CH 2 CS 2 - →C 6 H ^ 5 CH 2 - CHC（S）SH→[（C
• Photoinduced Desaturation of Amides by Palladium Catalysis
  作者：Sen Yang、Huike Fan、Licheng Xie、Guangbin Dong、Ming Chen

  DOI：10.1021/acs.orglett.2c02594

  日期：2022.9.9

  their α,β-unsaturated counterparts is reported. The reaction does not require strong base/acid or sulfur/selenium and oxidant reagents and can be carried out at room temperature through a simple one-step operation. The protocol exhibits great scalability and functional group tolerance. The reaction mechanism has been investigated through deuterium labeling experiments, radical clock, radical capture

  报道了一种适用于将线性酰胺转化为其 α,β-不饱和对应物的光诱导钯催化去饱和方法。该反应不需要强碱/酸或硫/硒和氧化剂试剂，可通过简单的一步操作在室温下进行。该协议表现出极大的可扩展性和功能组耐受性。反应机理已通过氘标记实验、自由基时钟、自由基捕获和动力学研究进行了研究。机理研究表明涉及芳基/烷基钯自由基中间体的自由基途径。
• Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes
  作者：Michael P. Stanton、Jessica M. Hoover

  DOI：10.1021/acs.joc.2c02705

  日期：2023.2.3

  A copper-catalyzed decarboxylative elimination reaction of (hetero)aromatic propionic acids to vinyl (hetero)arenes has been developed. This method furnishes alkenes from carboxylic acids without the need for stochiometric Pb or Ag additives or expensive or specialized photocatalysts. A series of mechanistic experiments indicate that the reaction proceeds via benzylic deprotonation and subsequent radical

  已经开发了铜催化的（杂）芳族丙酸到乙烯基（杂）芳烃的脱羧消除反应。该方法无需化学计量的 Pb 或 Ag 添加剂或昂贵或专门的光催化剂即可从羧酸中提供烯烃。一系列机理实验表明，该反应通过苄基去质子化和随后的自由基脱羧进行；一种不同于涉及相关脱羧消除反应的单电子转移机制的途径。
• Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles
  作者：Yifeng Chen、Justin P. Romaire、Timothy R. Newhouse

  DOI：10.1021/jacs.5b02243

  日期：2015.5.13

  A highly practical and general palladium-catalyzed methodology for the alpha,beta-dehydrogenation of esters and nitriles is repotted. Generation of a zinc enolate or (cyanoalkyl)zinc species followed by the addition of an allyl oxidant and a palladium catalyst results in synthetically useful yields of alpha,beta-unsaturated esters, lactones, and nitriles. Preliminary mechanistic investigations are consistent with reversible beta-hydride elimination and turnover-limiting, propene-forming reductive elimination.