2-Methoxy-5-methylsulfonylbenzoyl chloride | 54110-33-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Methoxy-5-methylsulfonylbenzoyl chloride
• 英文别名: 2-methoxy-5-methyl sulphonyl-benzoyl chloride
• CAS: 54110-33-7
• 化学式: C₉H₉ClO₄S
• 分子量: 248.687
• InChiKey: RCFGFTLCCWRMTI-UHFFFAOYSA-N

物化性质

• 沸点：
  443.2±45.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methoxy-5-methylsulfonylbenzoyl chloride 在 盐酸 、 伯吉斯试剂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 5.17h， 生成 2-(2-methoxy-5-(methylsulfonyl)phenyl)oxazole
  参考文献：
  名称：

  Color Tuning of Efficient Electroluminescence in the Blue and Green Regions Using Heteroleptic Iridium Complexes with 2-Phenoxyoxazole Ancillary Ligands

  摘要：

  A rational molecular design strategy for tuning the emission color of phosphorescent complexes by functionalization of the bis(2-phenylpyridine)(2-(2'-oxypheny1)-2-oxazoline/oxazole)iridium(III) framework is reported. Five new complexes (2-6) have been synthesized in good yields and characterized by cyclic voltamrnetry, absorption, and photoluminescence studies, by time-dependent density functional theory (TD-DFT) calculations, and by single-crystal Xray diffraction studies for complexes 2, 4, and 6. An interesting feature of the complexes is that the HOMO is localized on the Ir d-orbitals and the phenoxylate part of the "ancillary" ligand, while the LUMO is located on the pyridyl ring of the ppy ligands. A few other complexes containing 2'-oxyphenyl-2-oxazoline/oxazole ancillary ligands have been reported previously; however, until now there has not been a systematic investigation into manipulating this unusual frontier orbital distribution to tune the emissive properties. It is shown that exchanging the phenylpyridine (ppy) ligand for 2,4-difluoro-ppy gives a blue shift of 21-22 nm (from 1 to 2 and from 4 to 5), and the introduction of electron-withdrawing substituents (SO2Me, CF3) onto the phenoxylate ring of the (2'-oxyphenyl)-2-oxazole ligand results in a further blue shift of 13-20 nm. Combining these functionalizations gives sky-blue emission with lambda(pl)(max) 476 and 479 run for complexes 5 and 6 in dichloromethane solution. The solution quantum yields of all the complexes are within the range phi(PL), 0.42-0.73. The observed lifetimes (tau(obs) = 1.52-3.01 mu s) and spectral profiles are indicative of phosphorescence from a mixture of ligand-centered and MLCT excited states. (TD-)DFT calculations are in close agreement with the observed photophysical and electrochemical properties of the complexes. Phosphorescent organic light-emitting diodes have been fabricated using complexes 2, 3, 5, and 6 as the emitter, doped in a 4,4'bis(N-carbazolyl)biphenyl host, giving efficient emission in the blue-green region. Notably, complex 5 gives lambda(EL)(max) 480 nm with a maximum brightness of 26150 cd m(-2)

  DOI：

  10.1021/acs.organomet.7b00161
• 作为产物：
  描述：

  硫比利 在 氯化亚砜 作用下， 反应 1.0h， 生成 2-Methoxy-5-methylsulfonylbenzoyl chloride
  参考文献：
  名称：

  Rational approach to highly potent and selective apoptosis signal-regulating kinase 1 (ASK1) inhibitors

  摘要：

  Many diseases are believed to be driven by pathological levels of reactive oxygen species (ROS) and oxidative stress has long been recognized as a driver for inflammatory disorders. Apoptosis signal regulating kinase 1 (ASK1) has been reported to be activated by intracellular ROS and its inhibition leads to a down regulation of p38-and JNK-dependent signaling. Consequently, ASK1 inhibitors may have the potential to treat clinically important inflammatory pathologies including renal, pulmonary and liver diseases. Analysis of the ASK1 ATP-binding site suggested that Gln756, an amino acid that rarely occurs at the GK+2 position, offered opportunities for achieving kinase selectivity for ASK1 which was applied to the design of a parallel medicinal chemistry library that afforded inhibitors of ASK1 with nanomolar potency and excellent kinome selectivity. A focused optimization strategy utilizing structure-based design resulted in the identification of ASK1 inhibitors with low nanomolar potency in a cellular assay, high selectivity when tested against kinase and broad pharmacology screening panels, and attractive physicochemical properties. The compounds we describe are attractive tool compounds to inform the therapeutic potential of ASK1 inhibition. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.12.041

文献信息

• New substituted heterocyclic benzamides, methods of preparing them and
  申请人：Societe d'Etudes Scientifiques et Industrielle de l'Ile de France

  公开号：US04673686A1

  公开（公告）日：1987-06-16

  There are provided new substituted heterocyclic benzamides and derivatives hereof which provide modifications on the central nervous system.

  这里提供了新的替代杂环苯甲酰胺及其衍生物，这些化合物对中枢神经系统产生改变。
• 2-alkoxy-N-(1-azabicyclo(2.2.2)oct-3-yl) benzamides and thiobenzamides
  申请人：A. H. Robins Company, Inc.

  公开号：US04717563A1

  公开（公告）日：1988-01-05

  A method of controlling emesis caused by non-platinum anti-cancer drugs with 2-alkoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamides and thiobenzamides having the formula ##STR1## wherein X is oxygen or sulfur; R.sub.1 is loweralkyl; and R.sub.2 is selected from the group consisting of hydrogen, halo, 4,5-benzo, methylsulfonyl, loweralkoxy or Am and n is 1 or 2, and the pharmaceutically acceptable acid addition salts thereof is disclosed.

  一种控制由非铂类抗癌药物引起的呕吐的方法，使用具有通式##STR1##的2-烷氧基-N-(1-氮杂双环[2.2.2]辛-3-基)苯甲酰胺和噻吩甲酰胺，其中X为氧或硫；R1为低级烷基；R2选自氢、卤素、4,5-苯并、甲磺酰基、低级烷氧基或Am，n为1或2，以及其药学上可接受的酸加成盐。
• Method of enhancing memory or correcting memory deficiency with
  申请人：A. H. Robins Company, Inc.

  公开号：US04605652A1

  公开（公告）日：1986-08-12

  A pharmaceutical method for improving memory or correcting memory deficiency is disclosed, utilizing compounds having the formula: ##STR1## wherein n.sup.1, n.sup.2, n.sup.3, and n.sup.4 =0 to 3; R.sup.1, R.sup.2, R.sup.3, and R.sup.4 =H, loweralkyl or phenyl; R.sup.5 =H or loweralkyl; X=O or S; Ar=phenyl, substituted phenyl, pyridinyl, furanyl, thienyl, methoxy-1H-benzotriazolyl, indolinyl, methoxyindolinyl, methoxypyrimidinyl, amino-methoxypyrimadinyl, 1,3-benzodioxolyl, or naphthalenyl, and the pharmaceutically acceptable acid addition salts, hydrates and alcoholates thereof.

  本发明公开了一种改善记忆或纠正记忆缺陷的药物方法，采用具有以下通式的化合物：##STR1##其中n1、n2、n3和n4=0至3；R1、R2、R3和R4=H、低级烷基或苯基；R5=H或低级烷基；X=O或S；Ar=苯基、取代苯基、吡啶基、呋喃基、噻吩基、甲氧基-1H-苯并三唑基、吲哚啉基、甲氧基吲哚啉基、甲氧基嘧啶基、氨基-甲氧基嘧啶基、1,3-苯并二氧杂环己二烯基或萘基，以及它们的药学上可接受的酸加成盐、水合物和醇盐。
• Method of using
  申请人：A. H. Robins Company, Incorporated

  公开号：US04722834A1

  公开（公告）日：1988-02-02

  A method of controlling emesis caused by anticancer drugs with 2-alkoxy-N-(1-azabicyclo[2.2.2]oct-3-yl) benzamide-N-oxides having the formula: ##STR1## wherein R.sub.1 is loweralkyl, and R.sub.2 is selected from the group consisting of hydrogen, halo, 4,5-benzo, methylsulfonyl, loweralkoxy or Am and n is 1 or 2, and the pharmaceutically acceptable acid addition salts thereof is disclosed.

  揭示了一种控制由抗癌药物引起的呕吐的方法，其中具有以下结构的2-烷氧基-N-(1-氮杂双环[2.2.2]辛-3-基)苯甲酰胺-N-氧化物：其中R.sub.1是较低的烷基，R.sub.2选自氢、卤素、4,5-苯基、甲磺酰基、较低的烷氧基或Am的群，n为1或2，以及其药用可接受的酸盐。
• Synthesis and Central Dopaminergic Effects of N-(4,6-Dimethyl-2-pyridinyl)benzamides
  作者：Saïd Bouhayat、Sylvie Piessard、Guillaume Le Baut、Louis Sparfel、Jean-Yves Petit、François Piriou、Lucien Welin

  DOI：10.1021/jm50001a004

  日期：1985.5

  N-(4,6-Dimethyl-2-pyridinyl)benzamides 1-24 and the corresponding tertiary derivatives 29-33 were synthesized and studied for possible dopamine-inhibitory properties by testing their effect on motility of naive and reserpinized mice. Unlike the orthopramides, they failed to show any antidopaminergic properties, but some of the secondary derivatives showed instead effects of postsynaptic dopaminergic

  合成了N-（4,6-二甲基-2-吡啶基）苯甲酰胺1-24和相应的三级衍生物29-33，并通过测试它们对幼稚和再固定化小鼠运动的影响来研究其对多巴胺的抑制作用。与原丙酰胺不同，它们没有显示出任何抗多巴胺能的特性，但是一些二级衍生物反而显示了突触后多巴胺能激动作用。随后研究了后一种化合物对利血平诱导的运动障碍的阿扑吗啡逆转以及对大鼠脑HVA水平的影响。化合物11在6-羟基多巴胺损伤的小鼠中引起的相反盘旋表明涉及直接机制。