[2'-²H]acetanilide | 169214-12-4

• 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: [2'-²H]acetanilide
• 英文别名: N-(2-deuteriophenyl)acetamide
• CAS: 169214-12-4
• 化学式: C₈H₉NO
• 分子量: 136.158
• InChiKey: FZERHIULMFGESH-UICOGKGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  [2'-²H]acetanilide 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 甲基溴化镁 、 copper diacetate 、 silver carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙醇 为溶剂， 反应 26.5h， 生成 普拉朵林
  参考文献：
  名称：

  Synthesis of indoles through Rh(III)-catalyzed C–H cross-coupling with allyl carbonates

  摘要：

  A practical Rh-catalyzed reaction was developed to achieve 2-alkyl-substituted indole synthesis. The reaction can tolerate a variety of synthetically important functional groups. The indole products can also be transformed into other important skeletons. Two bioactive compounds, that is indomethacin and pravadoline were prepared using the new method. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.11.065
• 作为产物：
  描述：

  N-乙酰苯胺 在 (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate 氘 作用下， 以 二氯甲烷 为溶剂， 生成 [2'-²H]acetanilide
  参考文献：
  名称：

  Organoiridium catalyzed hydrogen isotope exchange: ligand effects on catalyst activity and regioselectivity

  摘要：

  Several iridium complexes [Ir(cod)L(2)]X (L = phosphine ligand) were used as precatalysts for the exchange labeling of a range of model compounds with deuterium gas. Complexes with monodentate L (e.g. PMePh(2), PPh(3) and substituted derivatives thereof) catalyzed exchange selectively of hydrogens four bonds away from a coordinative heteroatom in the substrate, while those with bidentate L (bis(diphenylphosphino)ethane (dppe) and bis(diphenylphosphino)butane) catalyzed exchange of hydrogens both four and five bonds away from a coordinative heteroatom. At heavier loadings, some monodentate complexes also catalyzed five-bond labeling of some substrates. [Ir(cod)(dppe)]BF4 catalyzed the tritium labeling of methyl 6-methoxynaphth-2-ylacetate at C1 and C3.

  DOI：

  10.1016/s0022-328x(96)06413-3

文献信息

• Studies of hydrogen isotope scrambling during the dehalogenation of aromatic chloro‐compounds with deuterium gas over palladium catalysts
  作者：William J.S. Lockley、Niccolò A. E. Venanzi、Georgie J. Crane

  DOI：10.1002/jlcr.3878

  日期：2020.11

  catalyst with one prepared in situ by reduction of palladium trifluoroacetate with deuterium gas and dispersed upon micronised polytetrafluoroethylene led to much reduced scrambling (typically 0–6% compared with up to 40% for palladium on carbon) and to high atom% abundance, regiospecific labelling. The improved catalytic system now enables efficient polydeuteration via the dehalogenation of polyhalogenated

  使用同位素氢气对芳族卤化物进行催化脱卤是标记药物、生物化学品、环境试剂等的重要策略。为了扩展、改进和进一步了解这一过程，在四氢呋喃溶液中使用氘气和钯碳催化剂对模型芳基氯进行催化氘代脱卤过程中，对氘同位素与氚的扰乱进行了研究。富电子氯芳烃环的加扰程度最大。四氢呋喃溶剂和三乙胺碱不是不想要的朊的来源；相反，它主要来自催化剂的水含量，尽管其他来源的朊也可能存在于催化剂上。用一种制备的催化剂代替 Pd/C 催化剂通过用氘气原位还原三氟乙酸钯并分散在微粉化聚四氟乙烯上，可显着减少乱序（通常为 0-6%，而碳载钯最高可达 40%）和高原子百分比丰度，区域特异性标记。改进后的催化系统现在可以通过多卤化前体的脱卤实现高效的多氘化，使该过程可用于制备 MS 内标，并可能用于高比活性氚标记。
• Highly Effective Pd-Catalyzed ortho Olefination of Acetanilides: Broad Substrate Scope and High Tolerability
  作者：Byung Seok Kim、Chungsik Jang、Dong Jin Lee、So Won Youn

  DOI：10.1002/asia.201000613

  日期：2010.11.2

  Bring it on! An effective Pd‐catalyzed ortho olefination of various acetanilides has been developed. This transformation has a broad substrate scope and wide functional‐group tolerability, regardless of the electronic and steric properties of acetanilide substrates, providing a straightforward access to highly functionalized arenes.

  来吧！已经开发出一种有效的Pd催化的各种乙酰苯胺的邻位烯烃化反应。不管乙酰苯胺底物的电子和位阻特性如何，这种转化都具有广泛的底物范围和宽泛的官能团耐受性，可直接进入高度官能化的芳烃。
• An improved bidentate complex of iridium as a catalyst for hydrogen isotope exchange
  作者：John M. Herbert、Andrew D. Kohler、Alan H. McNeill

  DOI：10.1002/jlcr.921

  日期：2005.3.30

  Iridium(I) complexes 1, containing bidentate phosphines, and 3, with arsine ligands, are generated in situ. These species mediate hydrogen isotope exchange in a variety of aromatic substrates including benzyl ketones. Although the catalytic activities of complexes 1 and 3 are generally unexceptional, a logical step leads to the use of [ethylene-1,2-bis(diphenylarsine)](cyclooctadiene)iridium(I) tetrafluoroborate

  铱 (I) 配合物 1（含有双齿膦）和 3（含有胂配体）是原位生成的。这些物质介导了包括苄基酮在内的各种芳香族底物中的氢同位素交换。尽管配合物 1 和 3 的催化活性通常不例外，但合乎逻辑的步骤导致使用 [乙烯-1,2-双（二苯基胂）]（环辛二烯）铱（I）四氟硼酸盐 (5)，这是一种有效的催化剂芳基酮和苄基酮，并在其他底物中介导交换。版权所有 © 2005 John Wiley & Sons, Ltd.
• Deuteration of acetanilides and other substituted aromatics using [Ir(COD)(Cy3P)(Py)]PF6 as catalyst
  作者：D. Hesk、P. R. Das、B. Evans

  DOI：10.1002/jlcr.2580360514

  日期：1995.5

  Deuterium exchange labelling using [Ir(COD)(Cy3P)(Py)]PF6 as catalyst and deuterium gas was studied on a number of substituted acetanilides. In most cases products containing deuterium ortho to the anilide group were obtained with a high degree of enrichment. With one exception no evidence for meta, para or anilide methyl labelling was seen. The catalyst was also effective in the ortho deuteration of acetophenone, benzophenone and the β-lactam containing compound Sch 48461.

  研究了使用[Ir(COD)(Cy3P)(Py)]PF6作为催化剂和氘气对多种取代乙酰苯胺进行氘交换标记。在大多数情况下，获得的产物含有邻位苯胺基团的氘并具有高度富集。除一例外，没有发现间位、对位或苯胺甲基标记的证据。该催化剂还可有效用于苯乙酮、二苯甲酮和含 β-内酰胺化合物 Sch 48461 的邻位氘化。
• Digitally enhanced thin layer chromatography: further development and some applications in isotopic chemistry
  作者：Daniel P. Manthorpe、William J. S. Lockley

  DOI：10.1002/jlcr.3052

  日期：2013.9

  Improvements to thin layer chromatography (TLC) analysis can be made easily and cheaply by the application of digital colour photography and image analysis. The combined technique, digitally enhanced TLC (DE-TLC), is applicable to the accurate quantification of analytes in mixtures, to reaction monitoring and to other typical uses of TLC. Examples are given of the application of digitally enhanced TLC to: the deuteromethylations of theophylline to [methyl−2H3]caffeine and of umbelliferone to [2H3]7-methoxycoumarin; the selection of tertiary amine bases in deuterodechlorination reactions; stoichiometry optimisation in the borodeuteride reduction of quinizarin (1,4-dihydroxyanthraquinone) and to the assessment of xanthophyll yields in Lepidium sativum seedlings grown in deuterated media.

  通过应用数字彩色摄影和图像分析，可以轻松且廉价地改进薄层色谱 (TLC) 分析。数字增强 TLC (DE-TLC) 组合技术适用于混合物中分析物的精确定量、反应监测以及 TLC 的其他典型用途。给出了数字增强薄层色谱应用的例子：茶碱至[甲基-2H3]咖啡因的氘甲基化以及伞形酮至[2H3]7-甲氧基香豆素的氘甲基化；氘代脱氯反应中叔胺碱的选择；醌茜（1,4-二羟基蒽醌）的硼氘化物还原的化学计量优化以及在氘化培养基中生长的独行菜幼苗叶黄素产量的评估。