(1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid | 208655-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid
• 英文别名: 1-(Triisopropylsilyl)-1H-indole-3-boronic acid；[1-tri(propan-2-yl)silylindol-3-yl]boronic acid
• CAS: 208655-73-6
• 化学式: C₁₇H₂₈BNO₂Si
• 分子量: 317.311
• InChiKey: UWIXBYHAFCWSKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  384.8±48.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid 在 四(三苯基膦)钯 、 (-)-1,2-bis(2R,5R)-2,5-dimethylphospholano(benzene)(cyclooctadiene)rhodium(I) trifluoromethanesulfonate 、 四丁基氟化铵 、 氢气 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 为溶剂， 20.0~80.0 ℃ 、275.79 kPa 条件下， 反应 24.0h， 生成 methyl (2R,3S)-2-acetamido-3-(1H-indol-3-yl)butanoate
  参考文献：
  名称：

  A highly enantioselective asymmetric hydrogenation route to β-(2R,3S)-methyltryptophan

  摘要：

  Asymmetric hydrogenation of a protected (Z)-dehydro-beta-methyltryptophan derivative 2 with (R,R)-Me-DuPHOS-Rh catalysis was achieved in 97 % ee. Deprotection then afforded (2R,3S)-beta-methyltryptophan 1. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00604-2
• 作为产物：
  描述：

  在 氯化铵 作用下， 生成 (1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid
  参考文献：
  名称：

  A highly enantioselective asymmetric hydrogenation route to β-(2R,3S)-methyltryptophan

  摘要：

  Asymmetric hydrogenation of a protected (Z)-dehydro-beta-methyltryptophan derivative 2 with (R,R)-Me-DuPHOS-Rh catalysis was achieved in 97 % ee. Deprotection then afforded (2R,3S)-beta-methyltryptophan 1. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00604-2

文献信息

• [EN] NOVEL PYRIDIN-2(1H)ONE DERIVATIVES, THEIR PREPARATION AND THEIR USE FOR THE TREATMENT OF PAIN<br/>[FR] NOUVEAUX DÉRIVÉS DE PYRIDIN-2(1H)ONE, LEUR PRÉPARATION ET LEUR UTILISATION POUR LE TRAITEMENT DE LA DOULEUR
  申请人：INST NAT SANTE RECH MED

  公开号：WO2021064186A1

  公开（公告）日：2021-04-08

  The present invention concerns novel pyridin-2(1H)one derivatives, their process of preparation and their use in therapeutics, in particular as agents for treating and/or preventing pain.

  这项发明涉及新型吡啶-2(1H)酮衍生物，它们的制备过程以及它们在治疗学中的用途，特别是作为治疗和/或预防疼痛的药物。
• Pyridin-2(1H)one derivatives: A possible new class of therapeutics for mechanical allodynia
  作者：Alexia Visseq、Amélie Descheemaeker、Nicolas Pinto-Pardo、Lionel Nauton、Vincent Théry、Francis Giraud、Isabelle Abrunhosa-Thomas、Alain Artola、Fabrice Anizon、Radhouane Dallel、Pascale Moreau

  DOI：10.1016/j.ejmech.2019.111917

  日期：2020.2

  Mechanical Allodynia (MA), a frequent chronic pain symptom caused by innocuous stimuli, constitutes an unmet medical need, as treatments using analgesics available today are not always effective and can be associated with important side-effects. A series of 3,5-disubstituted pyridin-2(1H)-ones was designed, synthesized and evaluated in vivo toward a rat model of inflammatory MA. We found that the series rapidly and strongly prevented the development of MA. 3-(2-Bromophenyl)-5-(phenylamino)pyridin-2(1H)-one 69, the most active compound of the series, was also able to quickly reverse neuropathic MA in rats. Next, when 69 was evaluated toward a panel of 50 protein kinases (PK) in order to identify its potential biological target(s), we found that 69 is a p38 alpha MAPK inhibitor, a PK known to contribute to pain hypersensitivity in animal models. 3,5-Disubstituted pyridin-2(1H)-ones thus could represent a novel class of analgesic for the treatment of MA. (C) 2019 Elsevier Masson SAS. All rights reserved.
• ORGANIC ELECTROLUMINESCENT DEVICE
  申请人：Nippon Steel & Sumikin Chemical Co., Ltd.

  公开号：EP2617724B1

  公开（公告）日：2017-07-05
• NITROGENATED AROMATIC COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC ELECTRONIC DEVICE
  申请人：Nippon Steel & Sumikin Chemical Co., Ltd.

  公开号：EP2628743B1

  公开（公告）日：2016-02-24
• Synthesis of (3-Indolyl)heteroaromatics by Suzuki-Miyaura Coupling and Their Inhibitory Activity in Lipid Peroxidation
  作者：Atsushi Nishida、Naoki Miyashita、Mihoko Fuwa、Masako Nakagawa

  DOI：10.3987/com-02-s64

  日期：——

  A variety of (3-indolyl)heteroaromatic compounds were synthesized by Suzuki-Miyaura coupling of 3-indolylboronic acid and halogenated heteroaromatics. 2-(3-Indolyl)thiophene showed potent inhibitory activity against lipid peroxidation by rat liver microsome.