3-氟-5-碘苯酚 | 939771-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-氟-5-碘苯酚
• 英文名称: 3-fluoro-5-iodophenol
• CAS: 939771-60-5
• 化学式: C₆H₄FIO
• mdl: MFCD16999911
• 分子量: 238.0
• InChiKey: OGZQPUORKLLIGI-UHFFFAOYSA-N

物化性质

• 沸点：
  272.9±25.0 °C(Predicted)
• 密度：
  2.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险类别：
  8
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P310,P330,P332+P313,P362,P403+P233,P405,P501
• 危险品运输编号：
  1759
• 危险性描述：
  H302,H315,H318,H335
• 包装等级：
  III
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3-氟-5-碘苯酚 在 bis(triphenylphosphine)palladium(II) dichloride 、 铁粉 、 potassium carbonate 、 氯化铵 、 三乙胺 作用下， 以 乙醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (E)-4-amino-2-(3-(2-cyanovinyl)-5-fluorophenoxy)benzonitrile
  参考文献：
  名称：

  Efficient Discovery of Potent Anti-HIV Agents Targeting the Tyr181Cys Variant of HIV Reverse Transcriptase

  摘要：

  Non-nucleoside reverse transcriptase inhibitors (NNRTIs) that interfere with the replication of human immunodeficiency virus (HIV) are being pursued with guidance from molecular modeling including free-energy perturbation (FEP) calculations for protein inhibitor binding affinities. The previously reported pyrimidinylphenylamine 1 and its chloro analogue 2 are potent anti-HIV agents; they inhibit replication of wild-type HIV-1 in infected human T-cells with EC50 values of 2 and 10 nM, respectively. However, they show no activity against viral strains containing the Tyr181Cys (Y181C) mutation in HIV-RT. Modeling indicates that the problem is likely associated with extensive interaction between the dimethylallyloxy substituent and Tyr181. As an alternative, a phenoxy group is computed to be oriented in a manner diminishing the contact with Tyr181. However, this replacement leads to a roughly 1000-fold loss of activity for 3 (2.5 mu M). The present report details the efficient, computationally driven evolution of 3 to novel NNRTIs with sub-10 nM potency toward both wild-type HIV-1 and Y181C-containing variants. The critical contributors were FEP substituent scans for the phenoxy and pyrimidine rings and recognition of potential benefits of addition of a cyanovinyl group to the phenoxy ring.

  DOI：

  10.1021/ja2058583
• 作为产物：
  描述：

  3-氟-5-甲氧基苯胺 在 盐酸 、 三溴化硼 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 14.75h， 生成 3-氟-5-碘苯酚
  参考文献：
  名称：

  Efficient Discovery of Potent Anti-HIV Agents Targeting the Tyr181Cys Variant of HIV Reverse Transcriptase

  摘要：

  Non-nucleoside reverse transcriptase inhibitors (NNRTIs) that interfere with the replication of human immunodeficiency virus (HIV) are being pursued with guidance from molecular modeling including free-energy perturbation (FEP) calculations for protein inhibitor binding affinities. The previously reported pyrimidinylphenylamine 1 and its chloro analogue 2 are potent anti-HIV agents; they inhibit replication of wild-type HIV-1 in infected human T-cells with EC50 values of 2 and 10 nM, respectively. However, they show no activity against viral strains containing the Tyr181Cys (Y181C) mutation in HIV-RT. Modeling indicates that the problem is likely associated with extensive interaction between the dimethylallyloxy substituent and Tyr181. As an alternative, a phenoxy group is computed to be oriented in a manner diminishing the contact with Tyr181. However, this replacement leads to a roughly 1000-fold loss of activity for 3 (2.5 mu M). The present report details the efficient, computationally driven evolution of 3 to novel NNRTIs with sub-10 nM potency toward both wild-type HIV-1 and Y181C-containing variants. The critical contributors were FEP substituent scans for the phenoxy and pyrimidine rings and recognition of potential benefits of addition of a cyanovinyl group to the phenoxy ring.

  DOI：

  10.1021/ja2058583

文献信息

• Trifunctionalization of Aryl Iodides with Two Distinct Nitrogen and Carbon Electrophiles by Palladium/Norbornene Catalysis
  作者：Jing Wang、Hui Wang、Zihan Wang、Linqiang Li、Cheng Qin、Xinjun Luan

  DOI：10.1002/cjoc.202100467

  日期：2021.10

  highly chemo- and regioselective vicinal trifunctionalization of aryl iodides by palladium/norbornene (Pd/NBE) catalysis. The key feature of this new method is the introduction of two distinct nitrogen and carbon electrophiles, with a large gap in reactivity, for ortho-unsubstituted aryl iodides via an intermolecular and intramolecular C―H functionalization, respectively. Eight types of ipso terminations

  在此，我们报告了通过钯/降冰片烯 (Pd/NBE) 催化对芳基碘化物进行高度化学和区域选择性的邻位三官能化。这种新方法的关键特征是引入了两个不同的氮和碳亲电子的，在反应性有很大的差距，对邻-未被取代的芳基碘经由分别的分子内和分子CA€•ħ官能化，。八种类型的本位终端可以与两个邻位-amination和邻烷基化，得到多种多取代的苯并杂环支架。硅系衬底可以通过以下方式产生多官能芳烃单步操作。值得注意的是，这些产品表现出具有大斯托克斯位移的全色可调强荧光发射，并且产品 7r 可以作为荧光探针来特异性靶向活细胞中的溶酶体。
• 8-Azabicyclo[3.2.1]octane derivatives
  申请人：Napier Elizabeth Susan

  公开号：US20070185156A1

  公开（公告）日：2007-08-09

  The present invention relates to a 8-azabicyclo[3.2.1]octane derivative of Formula I, wherein each of the substituents is given the definition as set forth in the specification and claims, or a pharmaceutically acceptable salt thereof or solvate thereof. The present invention also relates to a pharmaceutical composition comprising an 8-azabicyclo[3.2.1]octane derivative in admixture with one or more pharmaceutically acceptable auxiliaries and to the use of the 8-azabicyclo[3.2.1]octane derivative in therapy.

  本发明涉及一种式I的8-氮杂双环[3.2.1]辛烷衍生物，其中每个取代基的定义如规范和声明中所述，或其药学上可接受的盐或溶剂。本发明还涉及一种药物组合物，其包括8-氮杂双环[3.2.1]辛烷衍生物与一种或多种药学上可接受的辅助剂混合，并且涉及在治疗中使用8-氮杂双环[3.2.1]辛烷衍生物。
• [EN] MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR<br/>[FR] MODULATEURS DU RÉGULATEUR DE LA CONDUCTANCE TRANSMEMBRANAIRE DE LA FIBROSE KYSTIQUE
  申请人：VERTEX PHARMA

  公开号：WO2022032068A1

  公开（公告）日：2022-02-10

  This disclosure provides modulators of Cystic Fibrosis Transmembrane Conductance Regulator (CFTR), pharmaceutical compositions containing at least one such modulator, methods of treatment of cystic fibrosis using such modulators and pharmaceutical compositions, and processes for making such modulators.

  这份披露提供了囊性纤维化跨膜传导调节因子（CFTR）的调节剂，包含至少一种这种调节剂的药物组合物，使用这种调节剂和药物组合物治疗囊性纤维化的方法，以及制造这种调节剂的过程。
• [EN] DIAMINOTRIAZINE COMPOUNDS AND THEIR USE AS HERBICIDES<br/>[FR] COMPOSÉS DE DIAMINOTRIAZINE ET LEUR UTILISATION EN TANT QU'HERBICIDES
  申请人：BASF SE

  公开号：WO2015162166A1

  公开（公告）日：2015-10-29

  The present invention relates to diaminotriazine compounds and to their use as herbicides. It also relates to agrochemical compositions for crop protection and to method for controlling unwanted vegetation. Formula (I) wherein p is 1 or 2; q is 0, 1, 2 or 3 provided that p+q is 1, 2, 3 or 4; Q is inter alia a chemical bond, O, S(O)m, CRq1 Rq2, NRq3, C(O), C(O)O, Ar is phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals RA, Ra is inter alia hydrogen, halogen, OH, CN, amino, NO2, C1-C6-alkyl, etc; Rb is inter alia halogen, OH, CN, amino, NO2, C1-C6-alkyl, etc.; R1 and R2 are inter alia H, OH, S(O)2NH2, CN, C1-C6-alkyI, etc; X is a radical selected from the group consisting of CR3R4R5, phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 radicals RAr; NR3aR3b, OR3c, S(O)kR3d, k being 1, 2 or 3; and including their agriculturally acceptable salts.

  该发明涉及二氨基三嗪类化合物及其作为除草剂的用途。还涉及用于作物保护的农药组合物以及控制不受欢迎植被的方法。其中p为1或2；q为0、1、2或3，但要求p+q为1、2、3或4；Q包括化学键、O、S(O)m、CRq1 Rq2、NRq3、C(O)、C(O)O，Ar为苯基，未取代或携带1、2、3、4或5个基团RA，Ra包括氢、卤素、羟基、氰基、氨基、硝基、C1-C6-烷基等；Rb包括卤素、羟基、氰基、氨基、硝基、C1-C6-烷基等；R1和R2包括H、羟基、S(O)2NH2、氰基、C1-C6-烷基等；X为从CR3R4R5、未取代或携带1、2、3、4或5个基团RAr的苯基、NR3aR3b、OR3c、S(O)kR3d中选择的基团，其中k为1、2或3；包括它们的农业上可接受的盐。
• 8-azabicyclo[3.2.1]octane derivatives
  申请人：N.V. Organon

  公开号：US07605170B2

  公开（公告）日：2009-10-20

  The present invention relates to a 8-azabicyclo[3.2.1] octane derivative of Formula I, wherein each of the substituents is given the definition as set forth in the specification and claims, or a pharmaceutically acceptable salt thereof or solvate thereof. The present invention also relates to a pharmaceutical composition comprising an 8-azabicyclo [-3.2.1] octane derivative in admixture with one or more pharmaceutically acceptable auxiliaries and to the use of the 8-azabicyclo[3.2.1] octane derivative in therapy.

  本发明涉及一种式I的8-氮杂双环[3.2.1]辛烷衍生物，其中每个取代基的定义如规范和权利要求中所述，或其药学上可接受的盐或溶剂。本发明还涉及一种药物组合物，其中包括8-氮杂双环[3.2.1]辛烷衍生物与一个或多个药学上可接受的辅助剂混合，并且涉及在治疗中使用8-氮杂双环[3.2.1]辛烷衍生物。