2,2,2-trifluoro-N-(2-methoxybenzyl)acetamide | 197235-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,2,2-trifluoro-N-(2-methoxybenzyl)acetamide
• 英文别名: 2-Methoxybenzylamine, N-trifluoroacetyl-；2,2,2-trifluoro-N-[(2-methoxyphenyl)methyl]acetamide
• CAS: 197235-34-0
• 化学式: C₁₀H₁₀F₃NO₂
• 分子量: 233.19
• InChiKey: RWHLYFHQJWZXNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-(2-methoxybenzyl)acetamide 在 sodium hydroxide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2,6-dichloro-3-[N-(2-methoxyphenyl)methyl]aminomethyl-5-phenylpyridine
  参考文献：
  名称：

  Generation of 3-piperidine(methan)amines and cyclic 3-piperidine-methanamines as potential substance P antagonists

  摘要：

  A general method is described for the synthesis of 3-piperidine(methan)amines and their cyclic analogues. The 3,5-dichloro-2H-1,4-oxazin-2-ones 6 and 3-aryl substituted analogues are reacted with acetylenic dienophiles yielding pyridines. Further catalytic hydrogenation and functional group transformation (1) or substitution (2-3) with ring closure reactions (4) followed by hydrogenation provided the 2,3,5-cis substituted piperidines 1-3 and a cis substituted [3,4-c]pyrrolopiperidine 4. These compounds have recently raised great interest due to their Substance P antagonist profiles. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00791-6
• 作为产物：
  描述：

  邻甲氧基苄胺 、 三氟乙酸酐 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以63%的产率得到2,2,2-trifluoro-N-(2-methoxybenzyl)acetamide
  参考文献：
  名称：

  由单一阴离子配体实现的苄胺，苯乙胺和苯丙胺衍生的酰胺的亚选择性CH硼化

  摘要：

  巧妙的定位：结合有远端阴离子磺酸盐基团的联吡啶配体可将铱催化的硼化反应引导至一系列含酰胺芳烃的间位。提出该选择性是氢键相互作用的结果，该氢键相互作用将铱金属中心正确定位在关键的CH活化中。

  DOI：

  10.1002/anie.201708967

文献信息

• Iridium-Catalyzed Benzylamine C–H Alkenylation Enabled by Pentafluorobenzoyl as the Directing Group
  作者：Xiao Yang、Rui Sun、Chunchun Zhang、Xueli Zheng、Maolin Yuan、Haiyan Fu、Ruixiang Li、Hua Chen

  DOI：10.1021/acs.orglett.8b04005

  日期：2019.2.15

  The first iridium-catalyzed oxidative alkeynylation of benzylamines with acrylates enabled by a new directing group pentafluorobenzoyl has been developed. The reaction proceeded efficiently in the presence of silver acetate as oxidant and chlorobenzene as solvent. A good range of benzylamines could be selectively monoalkenylated without interfering with further aza-Michael addition. The kinetic isotope

  已经开发出了由新的指向性基团五氟苯甲酰基实现的，首个铱催化的苄胺与丙烯酸酯的氧化炔基化反应。在乙酸银作为氧化剂和氯苯作为溶剂的存在下，反应有效地进行。大量的苄胺可以被选择性地单烯基化而不干扰进一步的氮杂-迈克尔加成。动力学同位素效应实验表明，CH活化不是限速步骤。此外，分离并确定了五元的iridacycle物种，并将其确定为可能的关键中间体。
• Quantitative Silylation Speciations of Primary Phenylalkyl Amines, Including Amphetamine and 3,4-Methylenedioxyamphetamine Prior to Their Analysis by GC/MS
  作者：Borbála Molnár、Blanka Fodor、Imre Boldizsár、Ibolya Molnár-Perl

  DOI：10.1021/acs.analchem.5b02599

  日期：2015.10.20

  nitrogen prior to their injection. Efficiences of the novel catalyzed trimethylsilylation (MSTFA) and our recently introduced (now, for A and MDA extended) acylation principle were contrasted. Catalyzed trimethylsilylation led to diTMS derivatives resulting in on average a 1.7 times larger response compared to the corresponding acylated species. Catalyzed trimethylsilylation of PPAAs, A, and MDA were characterized

  注意到一种新颖的定量三甲基甲硅烷基化方法，可衍生11种伯苯烷基胺（PPAA），包括苯丙胺（A）和3,4-亚甲二氧基苯丙胺（MDA）。用N-甲基-N触发完全衍生化的二三甲基甲硅烷基（diTMS）物种-（三甲基甲硅烷基）-三氟乙酰胺（MSTFA）试剂，随后通过GC / MS识别了新原理。在方法优化过程中，研究了溶剂（乙腈，ACN；乙酸乙酯，ETAC；吡啶，PYR）和催化剂（三甲基氯硅烷，TMCS；三甲基碘硅烷，TMIS）的互补影响：溶剂和催化剂的作用被证明是同等的至关重要的。使用MSTFA / PYR = 2 / 1–9 / 1（v / v）的试剂施加催化剂可获得最佳的，成比例的，巨大的响应。A和MDA需要TMIS，而其余的PPAA向diTMS产品也提供TMCS。类似于Molnar等用六甲基二和全氟羧酸（HMDS和PFCA）生成的衍生物（Anal.Chem.31：426-428中。 2015年
• Hexamethyldisilazane as an Acylation Generator for Perfluorocarboxylic Acids in Quantitative Derivatization of Primary Phenylalkyl Amines Confirmed by GC/MS and Computations
  作者：Borbála Molnár、Antal Csámpai、Ibolya Molnár-Perl

  DOI：10.1021/ac503786j

  日期：2015.1.20

  derivatization processes were determined by gas chromatography/mass spectrometry. Reaction conditions were optimized depending on reagents’ molar ratios, solvents, and temperatures applied. The new acylation method, in comparison to the traditional ones, obtained with trifluoroacetic anhydride, heptafluorobutyric anhydride, and N-methyl-bis(trifluoroacetamide), offers numerous advantages. Derivatives

  注意到使用六甲基二硅氮烷（HMDS）和全氟羧酸（PFCA）对伯苯基烷基胺（PPAA）进行新颖的选择性酰化。HMDS和三氟乙酸，HMDS和五氟丙酸或HMDS和七氟丁酸之类的偶合物触发PPAA的定量酰化反应。通过应用所有偶对衍生化苄基，2-苯基乙基，3-苯基丙基，4-苯基丁基胺及其相关取代形式，来表征工艺的选择性。脂肪胺是不反应的。通过气相色谱/质谱法确定衍生化过程中的鉴定，定量，比例和化学计量。根据试剂的摩尔比，溶剂和施加的温度对反应条件进行了优化。与传统方法相比，新的酰化方法N-甲基-双（三氟乙酰胺）具有许多优点。夫妻提供的衍生物可以直接注入到色谱柱中，避免了物种损失，节省了制备过程中的时间，工作和成本。由于传统试剂由于氮气干燥而过度蒸发，因此三氟酰化物质的损失证明为65％或更少。关于七氟丁酰基物质，它们的损失在25％至5％之间变化。用HMDS和PFCA对获得的统一的巨大响应归因于它们直接
• Generation of 3-piperidine(methan)amines and cyclic 3-piperidine-methanamines as potential substance P antagonists
  作者：Nele Knoops、Geert Deroover、Zhang Jidong、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(97)00791-6

  日期：1997.9

  A general method is described for the synthesis of 3-piperidine(methan)amines and their cyclic analogues. The 3,5-dichloro-2H-1,4-oxazin-2-ones 6 and 3-aryl substituted analogues are reacted with acetylenic dienophiles yielding pyridines. Further catalytic hydrogenation and functional group transformation (1) or substitution (2-3) with ring closure reactions (4) followed by hydrogenation provided the 2,3,5-cis substituted piperidines 1-3 and a cis substituted [3,4-c]pyrrolopiperidine 4. These compounds have recently raised great interest due to their Substance P antagonist profiles. (C) 1997 Elsevier Science Ltd.
• <i>meta</i> -Selective C−H Borylation of Benzylamine-, Phenethylamine-, and Phenylpropylamine-Derived Amides Enabled by a Single Anionic Ligand
  作者：Holly J. Davis、Georgi R. Genov、Robert J. Phipps

  DOI：10.1002/anie.201708967

  日期：2017.10.16

  Clever positioning: A bipyridine ligand incorporating a remote anionic sulfonate group directs iridium-catalyzed borylation to the meta-position on a range of amide-containing arenes. It is proposed that this selectivity is a result of a hydrogen bonding interaction to correctly position the iridium metal centre in the crucial C−H activation.

  巧妙的定位：结合有远端阴离子磺酸盐基团的联吡啶配体可将铱催化的硼化反应引导至一系列含酰胺芳烃的间位。提出该选择性是氢键相互作用的结果，该氢键相互作用将铱金属中心正确定位在关键的CH活化中。