1-chloronaphthalen-2-yl trifluoromethanesulfonate | 288399-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-chloronaphthalen-2-yl trifluoromethanesulfonate
• 英文别名: (1-chloronaphthalen-2-yl) trifluoromethanesulfonate
• CAS: 288399-62-2
• 化学式: C₁₁H₆ClF₃O₃S
• 分子量: 310.681
• InChiKey: OMYBTWZBKCKEBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-chloronaphthalen-2-yl trifluoromethanesulfonate 在 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 盐酸 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 9.0h， 生成 2-[(1-chloronaphthalen-2-yl)amino]ethanaminium chloride
  参考文献：
  名称：

  TRPM8 receptor antagonists

  摘要：

  作为Transient Receptor Potential阳离子通道亚家族M成员8（以下简称为TRPM8）的选择性拮抗剂的化合物，其化学式为：其中R选择自：- H、CN、NO2、SO2NH2、SO2NHR'和SO2NR'2，其中R'选择自直链或支链的C1-C4烷基；X选择自：- F、Cl、CH3、NH2和OHY选择自：- O、CH2、NH和SO2R1、R2、R3和R4，独立地选择自- H和直链或支链的C1-C4烷基；Z选择自：- NR6和R6R7N+，其中R6和R7独立地选择自：• H和直链或支链的C1-C4烷基R5是选择自：- H和直链或支链的C1-C4烷基Het是选择自：- 取代或未取代的吡咯基、取代或未取代的N-甲基吡咯基、取代或未取代的噻吩基、取代或未取代的呋喃基和取代或未取代的吡啶基。这些化合物在治疗依赖于TRPM8活性的病理病变如疼痛、癌症、炎症、缺血、神经退行性疾病、中风、精神障碍、炎症性疾病、泌尿系统疾病方面是有用的。

  公开号：

  EP2481727A1
• 作为产物：
  描述：

  2-萘酚 在 N-氯代丁二酰亚胺 、 氯化锆(IV) 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-chloronaphthalen-2-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Multicomponent Multicatalyst Reactions (MC)²R: One-Pot Synthesis of 3,4-Dihydroquinolinones

  摘要：

  A Rh/Pd/Cu catalyst system led to an efficient synthesis of dihydroquinolinones in one-pot, two operations. The reaction features the first triple metal-catalyzed transformations in one reaction vessel, without any intermediate workup. The conjugate-addition/amidation/amidation reaction sequence is highly modular, divergent, and practical.

  DOI：

  10.1021/ol4006008

文献信息

• [EN] TRPM8 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DES RÉCEPTEURS TRPM8
  申请人：DOMPE SPA

  公开号：WO2012101244A1

  公开（公告）日：2012-08-02

  Compounds acting as selective antagonists of Transient Receptor Potential cation channel subfamily M member 8 (hereinafter referred to as TRPM8), having formula (I), wherein R is selected from: - H, Br, CN, NO2, SO2NH2, SO2NHR' and SO2NR'2, where R' is selected from linear or branched C1-C4 alkyl; X is selected from: - F, C1, C1-C3 alkyl, NH2 and OH Y is selected from: - O, CH2, NH and SO2 R1 and R2, independently one from the other, are selected from - H, F and linear or branched C1-C4 alkyl; R3 and R4, independently one from the other, are selected from - H and linear or branched C1-C4 alkyl; Z is selected from: - NR6 and R6R7N+, where R6 and R7 independently one from the other, are selected from: • H and linear or branched C1-C4 alkyl R5 is a residue selected from: - H and linear or branched C1-C4 alkyl Het is a heteroaryl group selected from - a substituted or not substituted pyrrolyl, a substituted or not substituted N- methylpyrrolyl, a substituted or not substituted thiophenyl, a substituted or not substituted furyl and a substituted or not substituted pyridinyl. Said compounds are useful in the prevention and treatment of pathologies depending on TRPM8 activity such as pain, inflammation, ischaemia, neurodegeneration, stroke, psychiatric disorders, inflammatory conditions and urological disorders.

  作为Transient Receptor Potential阳离子通道亚家族M成员8（以下简称为TRPM8）的选择性拮抗剂的化合物，具有以下式（I），其中R选自：- H、Br、CN、NO2、SO2NH2、SO2NHR'和SO2NR'2，其中R'选自线性或支链的C1-C4烷基；X选自：- F、C1、C1-C3烷基、NH2和OH；Y选自：- O、CH2、NH和SO2；R1和R2，彼此独立地选自- H、F和线性或支链的C1-C4烷基；R3和R4，彼此独立地选自- H和线性或支链的C1-C4烷基；Z选自：- NR6和R6R7N+，其中R6和R7彼此独立地选自：• H和线性或支链的C1-C4烷基；R5是从- H和线性或支链的C1-C4烷基中选出的残基；Het是从- 取代或未取代的吡咯基、取代或未取代的N-甲基吡咯基、取代或未取代的噻吩基、取代或未取代的呋喃基和取代或未取代的吡啶基中选出的杂环芳基团。所述化合物在预防和治疗依赖于TRPM8活性的病理病变中具有用途，如疼痛、炎症、缺血、神经退行性、中风、精神障碍、炎症性疾病和泌尿系统疾病。
• Enantioselective Synthesis of Axially Chiral Biaryls by the Pd-Catalyzed Suzuki−Miyaura Reaction: Substrate Scope and Quantum Mechanical Investigations
  作者：Xiaoqiang Shen、Gavin O. Jones、Donald A. Watson、Brijesh Bhayana、Stephen L. Buchwald

  DOI：10.1021/ja104297g

  日期：2010.8.18

  computational studies used to determine the origin of stereoselectivity during the selectivity-determining reductive elimination step of the related coupling of tolyl boronic acid with naphthylphosphonate bromide that was reported in a previous publication (J. Am. Chem. Soc. 2000, 122, 12051-12052). These studies indicate that the stereoselectivity arises from a combination of weak -(C)H..O interactions

  我们报告了轴向手性联芳酰胺的有效合成，产率范围为 80-92%，对映选择性范围为 88-94% ee，采用不对称 Suzuki-Miyaura 工艺，Pd(OAc)(2) 和 KenPhos 作为配体。这些研究表明，富电子和缺电子的邻卤苯甲酰胺可以与 2-甲基-1-萘基硼酸和 2-乙氧基-1-萘基硼酸有效偶联。反应的产率和选择性与苯甲酰胺偶联伙伴上卤素取代基的性质无关。我们的研究表明，轴向手性杂环和联苯化合物也可以用这种方法合成。我们还报告了用于确定在甲苯基硼酸与萘基膦酸酯溴化物相关偶联的选择性决定还原消除步骤期间立体选择性起源的计算研究，该步骤在之前的出版物中报道过 (J. Am. Chem. Soc. 2000, 122 , 12051-12052)。这些研究表明，立体选择性源于弱 -(C)H..O 相互作用以及 CC 偶联过渡态中甲苯基和萘基膦酸酯加合物之间的空间相互作用。
• Aluminium-mediated aromatic C–F bond activation: regioswitchable construction of benzene-fused triphenylene frameworks
  作者：Naoto Suzuki、Takeshi Fujita、Konstantin Yu. Amsharov、Junji Ichikawa

  DOI：10.1039/c6cc07199f

  日期：——

  Aluminium-mediated selective synthesis of benzo[f]tetraphenes or benzo[g]chrysenes was achieved via aromatic C–F bond cleavage and regioselective C–C bond formation.

  通过芳香C-F键裂解和区域选择性C-C键形成，利用铝介导实现了苯并[f]四环或苯并[g]蒽的选择性合成。
• “On-Water,” Microwave-Assisted, Pd-Catalyzed Synthesis of Indoles from Imines and o-Difunctionalized Arenes
  作者：José Barluenga、Agustín Jiménez-Aquino、Fernando Aznar、Carlos Valdés

  DOI：10.1002/chem.201000753

  日期：——

  Regioselectively substituted indoles are prepared by a Pd‐catalyzed CC/CN bond‐forming sequence from imines and o‐dihaloarenes or o‐haloarene sulfonates. The heterogeneous reaction as a suspension in water and under microwave heating offers important advantages in comparison with the conventional reaction in an organic solvent, among them, operational simplicity, the employment of KOH solutions instead

  区域选择性取代的吲哚通过Pd催化的C中制备 C / C  N键形成序列从亚胺和ö -dihaloarenes或ö -haloarene磺酸盐。与在有机溶剂中的常规反应相比，在水中和微波加热下作为悬浮液的非均相反应具有重要的优势，其中包括操作简便，使用KOH溶液代替醇盐以及显着减少反应时间。
• Ligand exchange and stereodynamics in the cationic palladium(II)–π-allyl complex of 2,2′-bis(pyridyl)-1,1′-binaphthalene, a novel atropisomeric N,N-ligand
  作者：Jonathan P. H. Charmant、Ian A. Fallis、Neil J. Hunt、Guy C. Lloyd-Jones、Martin Murray、Thorsten Nowak

  DOI：10.1039/b000651n

  日期：——

  Racemic 2,2′-bis(pyridin-2-yl)-1,1′-binaphthalene (±)-6 was prepared in four synthetic steps from 2-naphthol. Resolution of the novel atropisomeric ligand 6 was effected by repeated preparation, recrystallisation and then liberation of the bis-tartrate salt (D and L). This affords both enantiomers of 6 (>96% enantiomeric excess, ee) whose absolute configurations were assigned by CD. The ligand 6 is stable towards racemisation (ΔG‡rac > 167 kJ mol−1) and the structure was confirmed by single crystal X-ray diffraction of the complex [ZnCl2(6)]. The structure and stereodynamics of the complex [Pd(η3-C3H5)(6)][OTf] (OTf = O3SCF3) which comprises a C2-symmetric ligand bound via Pd to a non-C2-symmetric allyl fragment was studied in detail in solution by 1-D and 2-D 1H NMR and in the solid state by single crystal X-ray diffraction. Apparent stereodynamic processes of the allyl ligand, as detected in solution by NMR, are shown to arise from ligand 6 stereodynamics and exchange. The ligand 6 represents the first compound/building block for a series of enantiomerically pure N,N-ligands that may be of utility in supramolecular co-ordination chemistry and in asymmetric catalysis.

  对映体2,2′-双(吡啶-2-基)-1,1′-双萘(±)-6是从2-萘酚通过四个合成步骤制备而成。新型的对映异构体配体6的分解是通过重复的制备、重结晶以及随后释放双酒石酸盐(D和L)实现的。这提供了6的两个对映体(对映体纯度超过96%，ee)，其绝对构型通过圆二色性(CD)被确定。配体6在对映互变方面是稳定的(ΔG‡rac > 167 kJ mol⁻¹)，其结构通过复合物[ZnCl2(6)]的单晶X射线衍射得到了确认。复合物[Pd(η³-C3H5)(6)][OTf](OTf = O3SCF3)的结构和立体动力学在溶液中通过一维和二维¹H NMR以及在固态中通过单晶X射线衍射进行了详细研究。通过NMR在溶液中检测到的烯丙基配体的明显立体动力学过程表明，源于配体6的立体动力学及其交换。配体6代表了一系列光学纯的N,N-配体的第一个化合物/构件，这些配体在超分子配位化学和不对称催化中可能具有应用价值。