3-三氟甲基甲酰苯胺 | 657-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-三氟甲基甲酰苯胺
• 中文别名: 3-三氟甲基甲酰苯胺α,α,α-Trifluoro-m-formotoluidide；3-(三氟甲基)甲酰苯胺
• 英文名称: N-(3-(trifluoromethyl)phenyl)formamide
• 英文别名: 3'-Trifluoromethylformanilide；N-[3-(trifluoromethyl)phenyl]formamide
• CAS: 657-78-3
• 化学式: C₈H₆F₃NO
• 分子量: 189.137
• InChiKey: PPECHNDWLRNHEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 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
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2924299090

制备方法与用途

类别：有毒物品
毒性分级：高毒
急性毒性：静脉-小鼠LD50为56毫克/公斤
可燃性危险特性：明火可燃；高温分解能释放氮氧化物和氟化物气体
储运特性：应存放在库房中，保持通风、低温和干燥，并与氧化剂及酸类分开存放
灭火剂：使用干粉、泡沫、二氧化碳或砂土进行灭火。

反应信息

• 作为反应物：
  描述：

  3-三氟甲基甲酰苯胺 在 1,3-di-tert-butyl-1,3,2-diaza phospholidine 2-oxide 、 bis(1,5-cyclooctadiene)nickel (0) 、 三甲基铝 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 1-methyl-3,4-dipropyl-7-(trifluoromethyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Ligand-Enabled Ni–Al Bimetallic Catalysis for Nonchelated Dual C–H Annulation of Arylformamides and Alkynes

  摘要：

  A bifunctional secondary phosphine oxide (SPO) ligand-controlled method was developed for Ni-Al-catalyzed nonchelated dual C-H annulation of arylformamides with alkynes, providing a series of substituted amide-containing heterocycles in <= 97% yield. The SPO-bound bimetallic catalysis proved to be critical to the reaction efficiency.

  DOI：

  10.1021/acs.orglett.0c00432
• 作为产物：
  描述：

  N-(2-(5-nitropyridin-2-yl)ethyl)-3-(trifluoromethyl)aniline 在 copper(l) iodide 、 2,2,6,6-四甲基哌啶氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以48%的产率得到3-三氟甲基甲酰苯胺
  参考文献：
  名称：

  Copper Promoted Aerobic Oxidative C(sp³)–C(sp³) Bond Cleavage of N-(2-(Pyridin-2-yl)-ethyl)anilines

  摘要：

  A strategy of aerobic oxidative C(sp³)-C(sp³) bond cleavage of N-ethylaniline derivatives bearing azaarenes for the synthesis of N-aryl formamides has been developed. This approach was carried out smoothly with the CuI/TEMPO/air system to give N-aryl formamides in yields of 50-90%. With this methodology, a mutagenically active compound was constructed in 90% yield. Moreover, the reaction also provided a one-pot synthetic tool for accessing a promoter of hematopoietic stem cells by difunctionalization in 61% yield.

  DOI：

  10.1021/acs.joc.9b02919

文献信息

• Electrochemical <i>N</i>-Formylation of Amines via Decarboxylation of Glyoxylic Acid
  作者：Dian-Zhao Lin、Jing-Mei Huang

  DOI：10.1021/acs.orglett.8b00698

  日期：2018.4.6

  A new method for the synthesis of formamides has been developed through electrochemical decarboxylative N-formylation of amines with glyoxylic acid. This protocol provides an efficient approach to formamides with a broad range of functional group tolerance under ambient conditions.

  通过用乙醛酸对胺进行电化学脱羧N-甲酰化，已开发出一种新的甲酰胺合成方法。该协议为环境条件下具有宽泛的官能团耐受性的甲酰胺提供了一种有效的方法。
• Synthesis, characterization, antibacterial and catalytic activity of a nanopolymer supported copper(ii) complex as a highly active and recyclable catalyst for the formamidation of arylboronic acids under aerobic conditions
  作者：Mahmoud Nasrollahzadeh、Ali Zahraei、Ali Ehsani、Mehdi Khalaj

  DOI：10.1039/c4ra02052a

  日期：——

  This paper reports on the synthesis and use of a nanopolymer supported copper(II) complex, as a separable catalyst for the formamidation of arylboronic acids under aerobic conditions. The catalyst was characterized using powder XRD, SEM, EDS, TGA-DTG and FT-IR spectroscopy. This method has the advantages of high yields, elimination of homogeneous catalysts, simple methodology and easy work up. Catalytic efficiency remains unaltered even after several repeated cycles. The synthesized catalyst is found to be more highly toxic towards Gram-positive bacteria than Gram-negative bacteria.

  本论文报道了合成和使用一种纳米聚合物负载的铜（II）配合物，作为在有氧条件下对芳基硼酸进行甲酰胺化的可分离催化剂。该催化剂通过粉末XRD、SEM、EDS、TGA-DTG和FT-IR光谱进行表征。这种方法具有高产率、消除均相催化剂、方法简便和易于后处理的优点。催化效率即使在多次重复循环后仍保持不变。合成的催化剂对革兰氏阳性菌的毒性比革兰氏阴性菌更高。
• HCl-mediated transamidation of unactivated formamides using aromatic amines in aqueous media
  作者：Sanjeev Dhawan、Pankaj Sanjay Girase、Vishal Kumar、Rajshekhar Karpoormath

  DOI：10.1080/00397911.2021.1989597

  日期：2021.12.17

  Abstract We report transamidation protocol to synthesize a range of secondary and tertiary amides from weakly nucleophilic aromatic and hetero-aryl amines with low reactive formamide derivatives, utilizing hydrochloric acid as catalyst. This current acid mediated strategy is beneficial because it eliminates the need for a metal catalyst, promoter or additives in the reaction, simplifies isolation and

  摘要 我们报告了使用盐酸作为催化剂，从弱亲核芳香族和杂芳基胺与低反应性甲酰胺衍生物合成一系列仲酰胺和叔酰胺的转酰胺协议。这种当前的酸介导策略是有益的，因为它消除了反应中对金属催化剂、促进剂或添加剂的需要，简化了分离和纯化。值得注意的是，这种方法通常用于以克级规模合成具有优异产率和高官能团耐受性的分子。
• FUSED HETEROCYCLIC DERIVATIVE AND USE THEREOF
  申请人：Sakai Nozomu

  公开号：US20090137595A1

  公开（公告）日：2009-05-28

  The present invention provides a fused heterocyclic derivative having a potent kinase inhibitory activity and use thereof. A compound represented by the formula (I): wherein each symbol is as defined in the specification, except a particular compound, or a salt thereof, and a pharmaceutical agent containing the compound or a prodrug thereof, which is a kinase (VEGFR, VEGFR2, PDGFR, Raf) inhibitor, an angiogenesis inhibitor, an agent for the prophylaxis or treatment of cancer, a cancer growth inhibitor or a cancer metastasis suppressor.

  本发明提供了一种具有强大激酶抑制活性的融合杂环衍生物及其用途。 一种由以下式（I）表示的化合物： 其中除了特定化合物或其盐外，每个符号如规范中定义，以及含有该化合物或其前药的药用剂，该化合物是激酶（VEGFR、VEGFR2、PDGFR、Raf）抑制剂，血管生成抑制剂，用于癌症的预防或治疗的药剂，癌症生长抑制剂或癌症转移抑制剂。
• Catalyst free <i>N</i>-formylation of aromatic and aliphatic amines exploiting reductive formylation of CO₂ using NaBH₄
  作者：Arun Kumar、Pankaj Sharma、Nidhi Sharma、Yashwant Kumar、Dinesh Mahajan

  DOI：10.1039/d1ra04848a

  日期：——

  Herein, we report a sustainable approach for N-formylation of aromatic as well as aliphatic amines using sodium borohydride and carbon dioxide gas. The developed approach is catalyst free, and does not need pressure or a specialized reaction assembly. The reductive formylation of CO2 with sodium borohydride generates formoxy borohydride species in situ, as confirmed by 1H and 11B NMR spectroscopy.

  在此，我们报告了一种使用硼氢化钠和二氧化碳气体对芳香胺和脂肪胺进行 N-甲酰化的可持续方法。所开发的方法无需催化剂，并且不需要压力或专门的反应装置。 1H 和 11B NMR 光谱证实，CO2 与硼氢化钠的还原甲酰化会原位生成甲氧基硼氢化物物质。甲氧基硼氢化物的原位形成在甲酰胺基溶剂中非常突出，对于 N-甲酰化反应的成功至关重要。还发现甲氧基硼氢化物作为竞争途径促进转酰胺基反应，同时 与胺的还原官能化导致胺的 N-甲酰化。

表征谱图