(2-氯-6-氟-苯基)甲基磺酰氯 | 926257-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2-氯-6-氟-苯基)甲基磺酰氯
• 中文别名: (2-氯-6-氟苯基)甲烷磺酰氯
• 英文名称: (2-chloro-6-fluorophenyl)methanesulfonyl chloride
• CAS: 926257-07-0
• 化学式: C₇H₅Cl₂FO₂S
• mdl: MFCD09045976
• 分子量: 243.086
• InChiKey: VFDXEVWUTIVWCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2904909090

反应信息

• 作为反应物：
  描述：

  (2-氯-6-氟-苯基)甲基磺酰氯 在 palladium diacetate 、 sodium sulfate 、 三乙胺 、 silver carbonate 、 N-乙酰甘氨酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 2-cyano-5-methoxyphenyl (6-chloro-2-fluoro-3-(trimethylsilyl)phenyl)methanesulfonate
  参考文献：
  名称：

  Palladium-Catalyzed Remotemeta-Selective C–H Bond Silylation and Germanylation

  摘要：

  Selective meta-C-H activation of arenes to date has met with a limited number of functionalizations. Expanding the horizon of meta-C-H functionalization, herein we disclose an unprecedented meta-silylation and -germanylation protocol by employing a simple nitrile-based directing template. Longer linkers between the target site and the directing template were successfully explored for meta-silylation (sp(2)-epsilon and sp(2)-zeta). Additionally, synthetic utility was demonstrated with several postsynthetic elaborations and with a formal synthesis of TAC101, a promising drug for the treatment of lung cancer.

  DOI：

  10.1021/acs.organomet.7b00309
• 作为产物：
  描述：

  2-氯-6-氟氯苄 在 硫脲 、 盐酸 、 N-氯代丁二酰亚胺 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 4.25h， 生成 (2-氯-6-氟-苯基)甲基磺酰氯
  参考文献：
  名称：

  Palladium-Catalyzed Remotemeta-Selective C–H Bond Silylation and Germanylation

  摘要：

  Selective meta-C-H activation of arenes to date has met with a limited number of functionalizations. Expanding the horizon of meta-C-H functionalization, herein we disclose an unprecedented meta-silylation and -germanylation protocol by employing a simple nitrile-based directing template. Longer linkers between the target site and the directing template were successfully explored for meta-silylation (sp(2)-epsilon and sp(2)-zeta). Additionally, synthetic utility was demonstrated with several postsynthetic elaborations and with a formal synthesis of TAC101, a promising drug for the treatment of lung cancer.

  DOI：

  10.1021/acs.organomet.7b00309

文献信息

• <i>para</i> ‐Selective Arylation of Arenes: A Direct Route to Biaryls by Norbornene Relay Palladation
  作者：Uttam Dutta、Sandip Porey、Sandeep Pimparkar、Astam Mandal、Jagrit Grover、Adithyaraj Koodan、Debabrata Maiti

  DOI：10.1002/anie.202005664

  日期：2020.11.16

  components and pharmaceuticals. Selective synthesis of biaryls by distinguishing the subtle reactivity difference of distal arene C−H bonds are significantly challenging. Herein, we describe para‐selective C−H arylation, which is acheived by a unique combination of a meta‐directing group and norbornene as a transient mediator. Upon direct meta‐C−H palladation, one‐bond relay palladation occurs in presence of

  联芳基化合物是天然产物，生物活性成分和药物中极为重要的结构基序。通过区分远端芳烃CH键的微妙的反应性差异来选择性合成联芳基具有很大的挑战性。在本文中，我们描述了对位选择性CH芳基化，这是通过元导向基团和降冰片烯作为瞬时介体的独特组合而实现的。当直接元-C-H palladation，一键中继palladation发生在降冰片烯和随后的存在对带有2,6-二取代模式的磺酸盐，膦酸盐和苯酚可实现‐CH芳基化反应。该协议适用于缺电子的芳基碘化物。通过产物的后合成改性获得多取代的芳烃和苯酚。该协议允许通过顺序选择性的远端CH功能化来合成六取代的苯。
• Palladium‐Catalyzed Selective <i>meta</i> ‐C−H Deuteration of Arenes: Reaction Design and Applications
  作者：Sukdev Bag、Martin Petzold、Aishanee Sur、Suman Bhowmick、Daniel B. Werz、Debabrata Maiti

  DOI：10.1002/chem.201901317

  日期：2019.7.17

  Deuterium‐labeled compounds find wide applications in kinetic studies, and within the pharmaceutical industry. An easily removable pyrimidine‐based auxiliary has been employed for the meta‐C−H deuteration of arenes. The scope of this Pd‐catalyzed deuteration using commercially available [D1]‐ and [D4]‐acetic acid has been demonstrated by its application in phenylacetic acid and phenylmethanesulfonate

  氘标记的化合物在动力学研究以及制药行业中都有广泛的应用。容易去除的基于嘧啶辅助已被用于该元芳烃的-C-H氘化。使用可商购获得的[D 1 ]-和[D 4 ]-乙酸的Pd催化氘代反应的范围已通过在苯乙酸和苯甲磺酸酯衍生物中的应用得到证明。详尽的机理研究使我们探索了非速率确定的CH活化步骤的可逆性。元的当前研究氘掺入以选择性的方式说明了模板的形态。通过将氘选择性掺入各种药物中已证明了该方法的适用性。
• Template-Assisted<i>meta</i>-C−H Alkylation and Alkenylation of Arenes
  作者：Sukdev Bag、Ramasamy Jayarajan、Rahul Mondal、Debabrata Maiti

  DOI：10.1002/anie.201611360

  日期：2017.3.13

  alcohols, by meta‐C−H activation of benzylsulfonyl esters is described. In addition, α,β‐unsaturated aldehydes were generated by in situ olefination and deprotection of allyl benzyl ethers. These new functionalizations at the meta‐position of an arene have also been successfully implemented in benzylphosphonate, phenethyl carbonyl, and phenethylsulfonyl ester scaffolds. Key to these successful new functionalizations

  到扩大的范围的元-functionalization，有效地形成β -芳基醛和酮的，使用烯丙基醇，通过基于嘧啶模板元苄酯的-C-H活化进行说明。此外，α，β-不饱和醛是通过烯丙基苄基醚的原位烯烃化和脱保护而生成的。元上的这些新功能芳烃的位置也已成功地用于苄基膦酸酯，苯乙基羰基和苯乙基磺酰基酯支架中。这些成功的新功能化的关键是通过接受从金属到嘧啶环的能量低的π轨道的电子云来创建正电的钯中心，它有利于烯丙醇与金属中心的配位。
• [EN] N-HYDROXYMETHANESULFONAMIDE NITROXYL DONORS<br/>[FR] DONNEURS DE NITROXYLE N-HYDROXYMETHANESULFONAMIDE
  申请人：CARDIOXYL PHARMACEUTICALS INC

  公开号：WO2015109210A1

  公开（公告）日：2015-07-23

  The disclosed subject matter provides N-hydroxymethanesulfonamide compounds, pharmaceutical compositions and kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the disclosed subject matter provides methods of using such compounds or pharmaceutical compositions for treating heart failure.

  公开的主题提供了N-羟甲磺酰胺化合物、包含这种化合物的制药组合物和试剂盒，以及使用这种化合物或制药组合物的方法。特别地，公开的主题提供了使用这种化合物或制药组合物治疗心力衰竭的方法。
• N-HYDROXYMETHANESULFONAMIDE NITROXYL DONORS
  申请人：Cardioxyl Pharmaceuticals, Inc.

  公开号：US20160046569A1

  公开（公告）日：2016-02-18

  The disclosed subject matter provides N-hydroxymethanesulfonamide compounds, pharmaceutical compositions and kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the disclosed subject matter provides methods of using such compounds or pharmaceutical compositions for treating heart failure.

  所披露的主题提供了N-羟甲磺酰胺化合物、包含这种化合物的制药组合物和试剂盒以及使用这种化合物或制药组合物的方法。特别地，所披露的主题提供了使用这种化合物或制药组合物治疗心力衰竭的方法。