1-(4-(三氟甲基)苯基)乙酮O-甲基肟 | 107496-43-5

• 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: 1-(4-(三氟甲基)苯基)乙酮O-甲基肟
• 英文名称: 1-(4-(trifluoromethyl)phenyl)ethan-1-one O-methyl oxime
• 英文别名: N-methoxy-1-[4-(trifluoromethyl)phenyl]ethanimine
• CAS: 107496-43-5
• 化学式: C₁₀H₁₀F₃NO
• mdl: MFCD28011027
• 分子量: 217.191
• InChiKey: ALGCFBPHBQMGTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  217.5±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-(三氟甲基)苯基)乙酮O-甲基肟 在 palladium on activated charcoal 氨 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (Rs)-1-[4-(三氟甲基)苯基]乙胺
  参考文献：
  名称：

  α-Methylation at benzylic fragment of N-aryl-N′-benzyl ureas provides TRPV1 antagonists with better pharmacokinetic properties and higher efficacy in inflammatory pain model

  摘要：

  SAR studies for N-aryl-N '-benzyl urea class of TRPV1 antagonists have been extended to cover alpha-benzyl alkylation. Alkylated compounds showed weaker in vitro potencies in blocking capsaicin activation of TRPV1 receptor, but possessed improved pharmacokinetic properties. Further structural manipulations that included replacement of isoquinoline core with indazole and isolation of single enantiomer led to TRPV1 antagonists like (R)-16a with superior pharmacokinetic properties and greater potency in animal model of inflammatory pain. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.105
• 作为产物：
  描述：

  4'-三氟甲基苯乙酮 、 甲氧基胺盐酸盐 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 1-(4-(三氟甲基)苯基)乙酮O-甲基肟
  参考文献：
  名称：

  铑（III）催化的磺胺酮对酮肟的氧化环化：吲唑的直接方法

  摘要：

  在吲哚合成中，铑（III）催化了酮肟的分子间CH-H胺化反应和碘代苯二乙酸酯使N-N键形成。各种官能团的耐受性良好，可提供中等至良好收率的相应产物。此外，硝基取代的酮肟在该反应中具有良好的相容性，从而以中等至良好的收率得到相应的产物。

  DOI：

  10.1021/acs.orglett.8b03488

文献信息

• Access to Branched Allylarenes via Rhodium(III)-Catalyzed C–H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate
  作者：Shang-Shi Zhang、Yi-Chuan Zheng、Zi-Wu Zhang、Shao-Yong Chen、Hui Xie、Bing Shu、Jia-Lin Song、Yan-Zhi Liu、Yao-Fu Zeng、Luyong Zhang

  DOI：10.1021/acs.orglett.1c01832

  日期：2021.8.6

  A rhodium(III)-catalyzed C–H allylation of (hetero)arenes by using 2-methylidenetrimethylene carbonate as an efficient allylic source has been developed for the first time. Five different directing groups including oxime, N-nitroso, purine, pyridine, and pyrimidine were compatible, delivering various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields.

  首次开发了使用 2-亚甲基亚甲基碳酸酯作为有效烯丙基来源的铑（III）催化（杂）芳烃的 C-H 烯丙基化反应。五种不同的导向基团包括肟、N-亚硝基、嘌呤、吡啶和嘧啶是相容的，以中等至极好的产率提供带有烯丙基羟基的各种支链烯丙基芳烃。
• Rhodium-Catalyzed Intermolecular Amidation of Arenes with Sulfonyl Azides via Chelation-Assisted C–H Bond Activation
  作者：Ji Young Kim、Sae Hume Park、Jaeyune Ryu、Seung Hwan Cho、Seok Hwan Kim、Sukbok Chang

  DOI：10.1021/ja303527m

  日期：2012.6.6

  We report the direct amidation of arene C-H bonds using sulfonyl azides as the amino source to release N(2) as the single byproduct. The reaction is catalyzed by a cationic rhodium complex under external oxidant-free conditions in the atmospheric environment. A broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thus opening a new avenue

  我们报告使用磺酰叠氮化物作为氨基源释放 N(2) 作为单一副产品的芳烃 CH 键的直接酰胺化。该反应在大气环境中的外部无氧化剂条件下由阳离子铑络合物催化。广泛的含螯合基团的芳烃被选择性酰胺化，具有优异的官能团耐受性，从而为实际分子间 CN 键的形成开辟了新途径。
• Palladium-Catalyzed C(sp²)–H Acetoxylation via Electrochemical Oxidation
  作者：Yi-Qian Li、Qi-Liang Yang、Ping Fang、Tian-Sheng Mei、Dayong Zhang

  DOI：10.1021/acs.orglett.7b01138

  日期：2017.6.2

  Palladium-catalyzed arene C(sp2)–H acetoxylation has emerged as a powerful tool to construct a carbon–oxygen (C–O) bond. However, the requirement of stoichiometric chemical oxidants for this transformation possesses a significant disadvantage. To solve this fundamental problem, we now report an anodic oxidation strategy to achieve arene C(sp2)–H acetoxylation.

  钯催化的芳烃C（sp 2）-H乙酰氧基化已成为构建碳-氧（C-O）键的强大工具。然而，这种转化需要化学计量的化学氧化剂具有明显的缺点。为了解决这个基本问题，我们现在报告一种阳极氧化策略，以实现芳烃C（sp 2）–H乙酰氧基化。
• Palladium-catalyzed decarboxylative acylation of O-methyl ketoximes with α-keto acids
  作者：Minyoung Kim、Jihye Park、Satyasheel Sharma、Aejin Kim、Eonjeong Park、Jong Hwan Kwak、Young Hoon Jung、In Su Kim

  DOI：10.1039/c2cc38433g

  日期：——

  A mild, practical and efficient palladium-catalyzed decarboxylative ortho-acylation of O-methyl ketoximes with α-keto acids via C–H bond activation is described. In these reactions, a broad range of O-methyl ketoximes and α-keto acids undergoes the decarboxylative cross-coupling reactions with high selectivities and good tolerance.

  描述了一种温和、实用且高效的钯催化脱羧邻位酰基化反应，该反应通过C‒H键活化实现了O-甲基酮肟与α-酮酸的转化。在这些反应中，广泛的O-甲基酮肟和α-酮酸都能以高选择性和良好的耐受性进行脱羧交叉偶联反应。
• Direct CH Amination of Arenes with Alkyl Azides under Rhodium Catalysis
  作者：Kwangmin Shin、Yunjung Baek、Sukbok Chang

  DOI：10.1002/anie.201302784

  日期：2013.7.29

  New horizons in the utility of azides: The rhodium‐catalyzed intermolecular direct CH amination of arenes with alkyl azides provides a convenient route to N‐alkyl anilines (see scheme; DG=directing group). Alkyl azides with a wide range of functional groups reacted readily with various substrates, including benzamides, aromatic ketones, and flavones.

  叠氮化物应用的新视野：用烷基叠氮化物进行铑催化的芳烃分子间直接CH胺化反应可提供一条通往N烷基苯胺的便捷途径（参见方案； DG =导向基团）。具有多种官能团的烷基叠氮化物易于与各种底物反应，包括苯甲酰胺，芳族酮和黄酮。