N,N,3-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | 1421275-63-9

• 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: N,N,3-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS: 1421275-63-9
• 化学式: C₁₅H₂₄BNO₂
• 分子量: 261.172
• InChiKey: PNTRVGPVAQURRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N,3-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 、 5-溴-2-碘甲苯 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 以86%的产率得到4-bromo-4'-(N,N-dimethylamino)-2,2'-dimethyl-1,1'-biphenyl
  参考文献：
  名称：

  Design of donor–acceptor geometry for tuning excited-state polarization: fluorescence solvatochromism of push–pull biphenyls with various torsional restrictions on their aryl–aryl bonds

  摘要：

  In this work, push pull biphenyl analogs (4-(N,N-dimethylamino)-4'-formylbiphenyl) with a modulated dihedral angle of the aryl aryl bond, using a bridged structure or methyl groups, were synthesized. Photophysical measurements of the synthesized compounds revealed the effect of the torsion between N,N-dimethylaniline (donor) and benzaldehyde moieties (acceptor) on their solvatochromic properties. Our data showed that the sensitivity of the fluorescence maxima to solvent polarity gradually increases as the biphenyl chromophore was restricted to a twisted conformation. This finding indicates that changing the torsional restrictions on the donor acceptor system can be a factor to take into account for the development of novel solvatochromic dyes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.08.002
• 作为产物：
  描述：

  N,N-二甲基-间甲基苯胺 在 三(五氟苯基)硼烷 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 49.0h， 生成 N,N,3-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
  参考文献：
  名称：

  富电子芳烃的催化Friedel–Crafts CH硼氢化反应：增加的烯烃加速速率

  摘要：

  在富电子芳族化合物与儿茶酚硼烷的亲电CHH硼化反应中，亲电硼的催化生成是由各种Lewis和Brønsted酸对BH键的杂化作用引发的，它仅形成硼离子。配体解离后，相应的硼离子在苯胺衍生物以及含氮杂环上进行区域选择性亲电芳香取代。使用B（C 6 F 5）3来优化催化作用作为引发剂，并且在不添加外部碱或二氢受体的情况下进行。为了确保这些Friedel-Crafts型反应的有效转换，通常需要高于80°C的温度。机理实验表明，释放氢的硼/硼离子的再生是决定速率的。这一发现最终导致人们发现，添加烯烃后，催化CHH硼化可以首次在室温下进行。

  DOI：

  10.1002/anie.201611536

文献信息

• Synthesis and Biological Activity of New 4-(Pyridin-4-yl)-(3-methoxy-5-methylphenyl)-1H-pyrazoles Derivatives as ROS Receptor Tyrosine Kinase Inhibitors
  作者：Byung Sun Park、Ibrahim M. El-Deeb、Kyung Ho Yoo、Dong Keun Han、Jin Sung Tae、So Ha Lee

  DOI：10.5012/bkcs.2012.33.11.3629

  日期：2012.11.20

  A series of new 4-(pyridin-4-yl)-(3-methoxy-5-methylphenyl)-1H-pyrazoles (6a-k & 7a-l) has been rationally designed based on the structure of the lead compound KIST301080, a selective ROS receptor tyrosine kinase inhibitor, in order to study the activity of ROS of this new class of inhibitors. The compounds were synthesized and screened against ROS kinase, where compound 6h showed moderate inhibitory

  基于先导化合物KIST301080的结构，合理设计了一系列新型4-(pyridin-4-yl)-(3-methoxy-5-methylphenyl)-1H-pyrazoles (6a-k & 7a-l)，一种选择性ROS受体酪氨酸激酶抑制剂，以研究这类新型抑制剂的ROS活性。合成化合物并针对 ROS 激酶进行筛选，其中化合物 6h 显示出中等抑制活性，IC50 值为 6.25 卮 该研究强调了吡唑环上乙腈基团的重要性以及远端氢键供体的重要性与吡啶部分相连的苯环。
• [EN] PYRROLOPYRIDAZINE COMPOUNDS AS KINASE INHIBITORS<br/>[FR] COMPOSÉS DE PYRROLOPYRIDAZINE UTILISÉS COMME INHIBITEURS DE KINASE
  申请人：GOSSAMER BIOSERVICES INC

  公开号：WO2022109492A1

  公开（公告）日：2022-05-27

  Described herein are inhibitors of JAK kinases, pharmaceutical compositions comprising them, processes for preparing them and uses of such inhibitors to treat or prevent diseases, disorders and conditions associated with kinase function.

  本文描述了JAK激酶抑制剂，包括它们的制药组合物、制备它们的过程以及使用这些抑制剂来治疗或预防与激酶功能相关的疾病、紊乱和病况。
• Discovery of (<i>E</i>)-3-(3-((2-Cyano-4′-dimethylaminobiphenyl-4-ylmethyl)cyclohexanecarbonylamino)-5-fluorophenyl)acrylic Acid Methyl Ester, an Intestine-Specific, FXR Partial Agonist for the Treatment of Nonalcoholic Steatohepatitis
  作者：Soyeon Shim、Maddeboina Krishnaiah、Madhusudana Reddy Sankham、Inha Kim、Yoseob Lee、Irin Shin、A Reum Oh、Hwa Jeong Lee、Thi Ngoc Lan Vu、Jongmi Park、Sun Choi、Seojeong Park、Youngjoo Kwon、Sungsoon Fang、Dae-Kee Kim

  DOI：10.1021/acs.jmedchem.2c00641

  日期：2022.7.28
• Catalytic Friedel–Crafts C−H Borylation of Electron‐Rich Arenes: Dramatic Rate Acceleration by Added Alkenes
  作者：Qin Yin、Hendrik F. T. Klare、Martin Oestreich

  DOI：10.1002/anie.201611536

  日期：2017.3.20

  In the electrophilic C−H borylation of electron‐rich aromatic compounds with catecholborane, the catalytic generation of the boron electrophile is initiated by heterolysis of the B−H bond by various Lewis and Brønsted acids, with a boronium ion formed exclusively. After ligand dissociation, the corresponding borenium ion undergoes regioselective electrophilic aromatic substitution on aniline derivatives

  在富电子芳族化合物与儿茶酚硼烷的亲电CHH硼化反应中，亲电硼的催化生成是由各种Lewis和Brønsted酸对BH键的杂化作用引发的，它仅形成硼离子。配体解离后，相应的硼离子在苯胺衍生物以及含氮杂环上进行区域选择性亲电芳香取代。使用B（C 6 F 5）3来优化催化作用作为引发剂，并且在不添加外部碱或二氢受体的情况下进行。为了确保这些Friedel-Crafts型反应的有效转换，通常需要高于80°C的温度。机理实验表明，释放氢的硼/硼离子的再生是决定速率的。这一发现最终导致人们发现，添加烯烃后，催化CHH硼化可以首次在室温下进行。
• Design of donor–acceptor geometry for tuning excited-state polarization: fluorescence solvatochromism of push–pull biphenyls with various torsional restrictions on their aryl–aryl bonds
  作者：Shunsuke Sasaki、Yosuke Niko、Andrey S. Klymchenko、Gen-ichi Konishi

  DOI：10.1016/j.tet.2014.08.002

  日期：2014.10

  In this work, push pull biphenyl analogs (4-(N,N-dimethylamino)-4'-formylbiphenyl) with a modulated dihedral angle of the aryl aryl bond, using a bridged structure or methyl groups, were synthesized. Photophysical measurements of the synthesized compounds revealed the effect of the torsion between N,N-dimethylaniline (donor) and benzaldehyde moieties (acceptor) on their solvatochromic properties. Our data showed that the sensitivity of the fluorescence maxima to solvent polarity gradually increases as the biphenyl chromophore was restricted to a twisted conformation. This finding indicates that changing the torsional restrictions on the donor acceptor system can be a factor to take into account for the development of novel solvatochromic dyes. (C) 2014 Elsevier Ltd. All rights reserved.