5-氟-1H-苯并三唑 | 18225-90-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 5-氟-1H-苯并三唑
• 中文别名: 6-氟-1H-苯并噻唑
• 英文名称: 5-fluoro-1H-benzo[d][1,2,3]triazole
• 英文别名: 5-fluoro-2H-benzotriazole
• CAS: 18225-90-6
• 化学式: C₆H₄FN₃
• mdl: MFCD00760403
• 分子量: 137.116
• InChiKey: SYGGDXKMRDPIKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  362.8±15.0 °C(Predicted)
• 密度：
  1.481±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  5-氟-1H-苯并三唑 在 溴 、 硝酸 作用下， 以 水 为溶剂， 反应 15.0h， 以22%的产率得到5-fluoro-4,6,7-tribromo-1H-benzotriazole
  参考文献：
  名称：

  Relative Role of Halogen Bonds and Hydrophobic Interactions in Inhibition of Human Protein Kinase CK2α by Tetrabromobenzotriazole and Some C(5)-Substituted Analogues

  摘要：

  To examine the relative role of halogen bonding and hydrophobic interactions in the inhibition of human CK2 alpha by 4,5,6,7-tetrabromobenzotriazole (TBBt), we have synthesized a series of 5-substituted benzotriazoles (Bt) and the corresponding 5-substituted 4,6,7-tribromobenzotriazoles (Br(3)Bt) and examined their inhibition of human CK2 alpha relative to that of TBBt. The various C(5) substituents differ in size (H and CH3), electronegativity (NH2 and NO2), and hydrophobicity (COOH and Cl). Some substituents were halogen bond donors (Cl, Br), while others were fluorine bond donors (F and CF3). Most of the 5-substituted analogues of Br(3)Bt (with the exception of COOH and NH2) exhibited inhibitory activity comparable to that of TBBt, whereas the 5-substituted analogues of the parent Bt were only weakly active (Br, Cl, NO2, CF3) or inactive. The observed effect of the volume of a ligand molecule pointed to its predominant role in inhibitory activity, indicating that presumed halogen bonding, identified in crystal structures and by molecular modeling, is dominated by hydrophobic interactions. Extended QSAR analysis additionally pointed to the monoanion and a preference for the N(1)-H protomer of the neutral ligand as parameters crucial for prediction of inhibitory activity. This suggests that the monoanions of TBBt and its congeners are the active forms that efficiently bind to CK2 alpha, and the binding affinity is coupled with protomeric equilibrium of the neutral ligand.

  DOI：

  10.1021/jp102848y
• 作为产物：
  描述：

  4-氟-1,2-苯二胺 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 以85%的产率得到5-氟-1H-苯并三唑
  参考文献：
  名称：

  在混合半导体材料中混合离子键和配位键：实现稳健且可溶液加工的共价/配位网络结构的通用方法

  摘要：

  无机半导体材料以其卓越的物理性能以及结构刚性和稳定性而闻名。然而，这些共价键合网络结构的溶解性和溶液加工性差长期以来一直是一个严重的缺点，限制了它们在许多重要应用中的使用。在这里，我们提出了一种独特而通用的方法来合成建立在周期性和无限无机模块上的坚固、可溶液加工和高度发光的混合材料。结构分析证实，所有化合物均由碘化铜 (CumIm+22-) 的一维阴离子链组成，通过 Cu-N 键与阳离子有机配体配位。配体的选择在配位模式（μ1-MC 或 μ2-DC）和 Cu-N 键强度中起着重要作用。µ2-DC 结构实现了极大抑制的非辐射衰减。橙色发光的 1D-Cu4I6(L6) 获得了 85% (λex = 360 nm) 和 76% (λex = 450 nm) 的创纪录高量子产率。温度相关的 PL 测量表明，磷光和热激活延迟荧光都有助于这些 1D-AIO 化合物的发射，并且 µ2-DC 结构的非辐射衰减程度远小于

  DOI：

  10.1021/jacs.9b13772

文献信息

• [EN] NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF<br/>[FR] STÉROÏDES NEUROACTIFS, COMPOSITIONS ET UTILISATIONS
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2015027227A1

  公开（公告）日：2015-02-26

  Described herein are neuroactive steroids of the Formula (I): or a pharmaceutically acceptable salt thereof; wherein -------, R1, R2, R5, A and L are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.

  本文描述了化学式（I）中的神经活性类固醇或其药用可接受盐；其中-------，R1，R2，R5，A和L如本文所定义。在某些实施例中，预期这些化合物将表现为GABA调节剂。本发明还提供了包括本发明化合物的药物组合物以及使用和治疗方法，例如用于诱导镇静和/或麻醉的方法。
• Zinc‐Catalysed N‐Iodosuccinimide‐Enabled Selective N2‐Olefination of Benzotriazoles with Alkenes
  作者：Lili Zhu、Lifang Tian、Hui Zhang、Lina Xiao、Wen Luo、Bin Cai、Haifeng Wang、Chunjie Wang、Guanglu Liu、Chaoyu Pei、Yahui Wang

  DOI：10.1002/adsc.201801303

  日期：——

  Herein, we describe a zinc‐catalysed N2‐selective olefination of benzotriazoles with unactivated alkenes and styrenes. The transformation is achieved by a N‐iodosuccinimide (NIS)‐mediated two‐step, one‐pot approach, proceeding through sequential regioselective β‐iodoalkylation of benzotriazoles with alkenes and a subsequent base‐promoted 1,2‐elimination. The N2‐selective β‐iodoalkylation of benzotriazoles

  在本文中，我们描述了苯并三唑与未活化的烯烃和苯乙烯的锌催化N 2选择性烯化反应。该转化是通过N碘代琥珀酰亚胺（NIS）介导的两步一锅法完成的，该方法通过依次进行苯并三唑与烯烃的区域选择性β碘烷基化和随后的碱促进的1,2消除。苯并三唑的N 2选择性β碘烷基化具有高度立体定向性，可在非常简单温和的条件下发挥作用，表现出出色的官能团耐受性。N 2的高选择性归因于N之间的分子间氢键碘代琥珀酰亚胺和苯并三唑的1位上的NH氢键供体。这种可扩展的过程，作为结构多样的N 2烯烃化苯并三唑的模块化组装的有效方法，将极大地促进苯并三唑的N 2功能化的化学反应。
• <i>tert</i>-Butyl nitrite mediated nitrogen transfer reactions: synthesis of benzotriazoles and azides at room temperature
  作者：Sadaf Azeez、Priyanka Chaudhary、Popuri Sureshbabu、Shahulhameed Sabiah、Jeyakumar Kandasamy

  DOI：10.1039/c8ob01950a

  日期：——

  A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.

  的A转换ö苯二胺为苯并三唑类是用在室温下实现叔丁基亚硝酸盐。优化的条件也非常适合将磺酰基和酰基肼转化为相应的叠氮化物。该协议不需要任何催化剂或酸性介质。在短时间内以优异的产率获得了所需的产物。
• [EN] COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS<br/>[FR] COMPOSITIONS ET MÉTHODES POUR TRAITER DES TROUBLES DU SNC
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2016061527A1

  公开（公告）日：2016-04-21

  Described herein are neuroactive steroids of the Formula (I): or a pharmaceutically acceptable salt thereof; wherein (II), A, R1, R2, R3a, R4a, R4b, R5, R7a, and R7b are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.

  本文描述了式(I)的神经活性类固醇，或其药用可接受盐；其中(II)，A，R1，R2，R3a，R4a，R4b，R5，R7a和R7b如本文所定义。在某些实施例中，这些化合物被设想为GABA调节剂。本发明还提供了包括本发明化合物的药物组合物，以及使用和治疗方法，例如用于诱导镇静和/或麻醉。
• Rhodium-catalyzed intermolecular hydroarylation of internal alkynes with N-1-phenylbenzotriazoles
  作者：Wang Zhou、Youqing Yang、Zhiwei Wang、Guo-Jun Deng

  DOI：10.1039/c3ob42007h

  日期：——

  A rhodium-catalyzed intermolecular hydroarylation of internal alkynes with N-1-phenylbenzotriazoles via C–H bond activation is described. This transformation offers an alternative method for the hydroarylation of internal alkynes with high stereoselectivity. The reaction mechanism was discussed according to the deuterium-labeling experiments.

  描述了一种铑催化的内炔与N-1-苯基苯并三嗪的分子间氢芳基化反应，采用C-H键活化。这一转化提供了一种高立体选择性的内炔氢芳基化的替代方法。根据氘标记实验讨论了反应机制。