5-(trifluoromethoxy)biphenyl-2-ylamine | 131395-27-2

• 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: 5-(trifluoromethoxy)biphenyl-2-ylamine
• 英文别名: 2-Amino-5-(trifluoromethoxy)biphenyl；2-phenyl-4-(trifluoromethoxy)aniline
• CAS: 131395-27-2
• 化学式: C₁₃H₁₀F₃NO
• 分子量: 253.224
• InChiKey: DNSUFAAFDZLIJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(trifluoromethoxy)biphenyl-2-ylamine 在 吡啶 、 silver(I) acetate 、 palladium diacetate 作用下， 以 乙腈 为溶剂， 反应 26.0h， 生成 5-tosyl-2-(trifluoromethoxy)phenanthridin-6(5H)-one
  参考文献：
  名称：

  Palladium-Catalyzed Oxidative Insertion of Carbon Monoxide to N-Sulfonyl-2-aminobiaryls through C–H Bond Activation: Access to Bioactive Phenanthridinone Derivatives in One Pot

  摘要：

  Palladium-catalyzed oxidative carbonylation of N-sulfonyl-2-aminobiaryls through C-H bond activation and C-C, C-N bond formation under TFA-free and milder conditions has been developed. The reaction tolerates a variety of substrates and provides biologically important phenanthrldlnone derivatives in yields up to 94%.

  DOI：

  10.1021/ol4001922
• 作为产物：
  描述：

  2-溴-4-三氟甲氧基苯胺 、 苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以92%的产率得到5-(trifluoromethoxy)biphenyl-2-ylamine
  参考文献：
  名称：

  钯催化和杂酸辅助在温和条件下在一锅中合成[60]富拉氮平：通过顺序C-H键活化，C-C和C-N使N-磺酰基-2-氨基联芳基与[60]富勒烯环化债券形成

  摘要：

  一个非常高效的混合酸辅助，钯-催化的和螯合基团的辅助Ç 的H键活化Ñ磺酰基-2- aminobiaryls及其与[60]富勒烯annulations经由连续的C语言 C和C  N键形成在室温下可得到[60]富勒氮杂。[60]富勒氮杂的形成具有高度的区域选择性，并且对芳基部分的吸电子基团和给电子基团都具有耐受性，并且该反应以良好的收率得到单官能化的富勒烯（分离出的C高达54％，基于转化的C 60高达92％）。

  DOI：

  10.1002/adsc.201200314

文献信息

• INDOLE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF
  申请人：Tatani Kazuya

  公开号：US20120129890A1

  公开（公告）日：2012-05-24

  A compound (I) of the present invention, which has an EP 1 receptor antagonism: [wherein A represents a benzene ring or the like; Y 1 represents a C 1-6 alkylene group; Y 2 represents a single bond or the like; R 1 represents a hydrogen atom, a C 1-6 alkyl group or the like; R 2 represents a phenyl group which may have a substituent, a 5-membered aromatic heterocyclic ring which may have a substituent, a 6-membered aromatic heterocyclic ring which may have a substituent or the like; R 3 represents a halogen atom, a C 1-6 alkoxy group or the like; R 4 represents a hydrogen atom or the like; and R 5 represents a hydrogen atom or the like] or a pharmaceutically acceptable salt thereof is provided. Furthermore, the compound (I) of the present invention can be used as an agent for treating or preventing LUTS, in particular, various symptoms of OABs.

  本发明提供了一种具有EP1受体拮抗作用的化合物（I）[其中A代表苯环或类似结构；Y1代表C1-6烷基亚基；Y2代表单键或类似结构；R1代表氢原子、C1-6烷基团或类似结构；R2代表可能含有取代基的苯基、可能含有取代基的5元芳香杂环、可能含有取代基的6元芳香杂环或类似结构；R3代表卤素原子、C1-6烷氧基团或类似结构；R4代表氢原子或类似结构；R5代表氢原子或类似结构]或其药物可接受的盐。此外，本发明的化合物（I）可用作治疗或预防LUTS的药物，特别是OAB的各种症状。
• Palladium-Catalyzed C–H Bond Activation by Using Iminoquinone as a Directing Group and an Internal Oxidant or a Co-oxidant: Production of Dihydrophenanthridines, Phenanthridines, and Carbazoles
  作者：Selvam Raju、Pratheepkumar Annamalai、Pei-Ling Chen、Yi-Hung Liu、Shih-Ching Chuang

  DOI：10.1021/acs.orglett.7b01956

  日期：2017.8.4

  A palladium-catalyzed C–H bond activation reaction, via a redox-neutral pathway, for the preparation of dihydrophenanthridine, phenanthridine, and carbazole derivatives from biaryl 2-iminoquinones is developed. The preinstalled iminoquinone was designed to act as a directing group for ortho C–H activation and an internal oxidant or a co-oxidant. This catalysis proceeded through the following sequence:

  通过氧化还原中性途径开发了钯催化的CH键活化反应，用于从联芳基2-亚氨基醌制备二氢菲啶，菲啶和咔唑衍生物。预先安装的亚氨基醌被设计成可作为邻位C–H活化的引导基团和内部氧化剂或助氧化剂。该催化过程按以下顺序进行：C–H键活化，活化烯烃的配位和插入，β-氢化物消除，H-移位，插入和质子化或β-氢化物消除。另外，通过使用该方法可以有效地制备咔唑，而无需添加外部氧化剂。
• Palladium(II)-Catalyzed Mono- and Bis-alkenylation of <i>N</i>-Acetyl-2-aminobiaryls through Regioselective C–H Bond Activation
  作者：Pratheepkumar Annamalai、Kou-Chi Hsu、Selvam Raju、Huan-Chang Hsiao、Chih-Wei Chou、Gu-Ying Lin、Cheng-Ming Hsieh、Pei-Ling Chen、Yi-Hung Liu、Shih-Ching Chuang

  DOI：10.1021/acs.joc.8b00194

  日期：2018.4.6

  We developed palladium-catalyzed oxidative coupling of olefins with N-acyl 2-aminobiaryls through a sequence of ortho C–H bond activation/alkene insertion/reductive elimination. Furthermore, we controlled the selectivity of mono- and bis-alkenylation products with the solvent effect. The developed protocol was promising for a broad substrate scope ranging from activated olefins with a wide variety

  我们通过一系列邻位碳氢键活化/烯烃插入/还原消除的过程，开发了钯与N-酰基2-氨基联芳基的钯催化氧化偶联反应。此外，我们通过溶剂效应控制了单链和双链烯基化产物的选择性。所开发的方案有望在从具有各种官能团的活化烯烃到未活化烯烃的广泛底物范围内进行。
• Palladium-Catalyzed Selective Aryl Ring C-H Activation of<i>N</i>-Acyl-2-aminobiaryls: Efficient Access to Multiaryl-Substituted Naphthalenes
  作者：Pratheepkumar Annamalai、Wu-Yin Chen、Selvam Raju、Kou-Chi Hsu、Nitinkumar Satyadev Upadhyay、Chien-Hong Cheng、Shih-Ching Chuang

  DOI：10.1002/adsc.201600488

  日期：2016.11.17

  Palladium‐catalyzed cycloaromatization of N‐acyl‐2‐aminobiaryls, through a sequence of ortho C−H bond activation/alkyne insertion/meta C−H bond activation/alkyne insertion, was developed. An efficient synthesis of multiaryl‐substituted naphthalenes, N‐[2‐(5,6,7,8‐tetraarylnaphthalen‐1‐yl)aryl]acetamides, was demonstrated using molecular oxygen as the sole oxidant. Furthermore, through Buchwald's synthetic

  通过一系列邻位CH键活化/炔烃插入/间位CH键活化/炔烃插入的过程，开发了N-酰基-2-氨基联芳基的钯催化环芳构化。使用分子氧作为唯一的氧化剂，证明了多芳基取代的萘，N- [2-（5,6,7,8-四芳基萘-1-基）芳基]乙酰胺的有效合成。此外，通过布赫瓦尔德（Buchwald）的合成方案，通过分子内C-N键的形成，两种化合物以30–40％的产率转化为相应的荧光咔唑。
• Dual role of ethyl bromodifluoroacetate in the formation of fluorine-containing heteroaromatic compounds
  作者：Xingxing Ma、Shaoyu Mai、Yao Zhou、Gui-Juan Cheng、Qiuling Song

  DOI：10.1039/c8cc04298e

  日期：——

  BrCF2COOEt plays a dual role as a C1 synthon and a difluoroalkylating reagent for the first time. Mechanistic studies supported by DFT calculations suggest that a base plays an active role in the formation of the key intermediate isocyanides generated in situ from primary amines and difluorocarbene.

  描述了一种有效的一锅级联过程，该过程通过将BrCF 2 COOEt与伯胺进行空前的四次裂解以提供有价值的含氟杂环，其中BrCF 2 COOEt首次扮演了C1合成子和二氟烷基化试剂的双重角色。DFT计算支持的机理研究表明，碱在伯胺和二氟卡宾就地生成的关键中间异氰酸酯的形成中起着积极作用。