6-ethoxy-2-phenylbenzothiazole | 101096-95-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 6-ethoxy-2-phenylbenzothiazole
• 英文别名: 6-ethoxy-2-phenylbenzo[d]thiazole；6-Ethoxy-2-phenyl-1,3-benzothiazole
• CAS: 101096-95-1
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: CBOLVOKGYICTJS-UHFFFAOYSA-N

物化性质

• 沸点：
  405.6±37.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 、 对乙氧基苯胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 氧气 、 potassium iodide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以79%的产率得到6-ethoxy-2-phenylbenzothiazole
  参考文献：
  名称：

  Assembly of 2-Arylbenzothiazoles through Three-Component Oxidative Annulation under Transition-Metal-Free Conditions

  摘要：

  Highly efficient methods for the synthesis of 2-arylbenzothiazoles and 2-arylnaphtho[2,1-d]thiazoles have been developed. Readily available aromatic amines, benzaldehydes, and elemental sulfur were directly assembled through oxidative annulation and C-H functionalization under transition-metal-free conditions, where DMSO or oxygen served as the oxidant. NH4I or KI as the catalyst was found to be effective to promote the transformations to give the annulation products in good to excellent yields with wide functional group tolerance.

  DOI：

  10.1021/acs.orglett.7b02168

文献信息

• [EN] PROTEOLYSIS TARGETING CHIMERIC (PROTAC) COMPOUND WITH E3 UBIQUITIN LIGASE BINDING ACTIVITY AND TARGETING ALPHA-SYNUCLEIN PROTEIN FOR TREATING NEURODEGENERATIVE DISEASES<br/>[FR] COMPOSÉ CHIMÈRE CIBLANT LA PROTÉOLYSE (PROTAC) AYANT UNE ACTIVITÉ DE LIAISON À L'UBIQUITINE LIGASE E3 ET CIBLANT UNE PROTÉINE ALPHA-SYNUCLÉINE POUR LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：ARVINAS OPERATIONS INC

  公开号：WO2020041331A1

  公开（公告）日：2020-02-27

  The present disclosure relates to bifunctional compounds, which find utility as modulators of alpha-synuclein (target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand which binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/ inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure. Such diseases or disorders are alpha-synucleinopathies or neurodegenerative diseases associated with alpha-synuclein accumulation and aggregation, such as e.g. Parkinson Disease, Alzheimer's Disease, dementia, dementia with Lewy bodies or multiple system atrophy, in particular Parkinson's Disease.

  本公开涉及双功能化合物，其作为α-突触核蛋白（目标蛋白）的调节剂具有实用性。具体而言，本公开涉及包含一端为Von Hippel-Lindau、cereblon、凋亡抑制蛋白或鼠双分子同源物2配体的双功能化合物，该配体与相应的E3泛素连接酶结合，另一端为与目标蛋白结合的基团，使得目标蛋白靠近泛素连接酶以促使目标蛋白的降解（和抑制）。本公开展示了与目标蛋白的降解/抑制相关的广泛药理活性范围。本公开的化合物和组合物用于治疗或预防由目标蛋白聚集或积累导致的疾病或紊乱。这些疾病或紊乱是与α-突触核蛋白积累和聚集相关的α-突触核蛋白病或神经退行性疾病，例如帕金森病、阿尔茨海默病、痴呆症、带有Lewy小体的痴呆症或多系统萎缩，特别是帕金森病。
• Copper-Catalyzed Oxidative Decarboxylative Arylation of Benzothiazoles with Phenylacetic Acids and α-Hydroxyphenylacetic Acids with O₂ as the Sole Oxidant
  作者：Qiuling Song、Qiang Feng、Mingxin Zhou

  DOI：10.1021/ol402871f

  日期：2013.12.6

  A Cu(II)-catalyzed oxidative decarboxylative synthesis of 2-aryl benzothiazole from phenylacetic acids and α-hydroxyphenylacetic acids has been developed. This reaction proceeds via Cu(II)-catalyzed decarboxylation, C–H bond oxidation, ring-opening, and condensation steps in a one-pot protocol with dioxygen as the sole terminal oxidant. Various functional groups were tolerated under standard conditions

  已经开发了一种由Cu（II）催化的由苯基乙酸和α-羟基苯基乙酸氧化合成2-芳基苯并噻唑的方法。该反应通过Cu（II）催化的脱羧反应，CH键的氧化，开环反应和一键操作规程中的缩合步骤进行，其中双氧为唯一的末端氧化剂。在标准条件下可以耐受各种官能团，分离的产率高达95％。
• Iron-catalyzed arylation of benzoazoles with aromatic aldehydes using oxygen as oxidant
  作者：Saiwen Liu、Ru Chen、Xiangyu Guo、Huiqiong Yang、Guojun Deng、Chao-Jun Li

  DOI：10.1039/c2gc35457h

  日期：——

  An iron-catalyzed arylation of azoles with aromatic aldehydes using oxygen as oxidant has been discovered. The reaction proceeded well for a range of different substrates under oxidative conditions.

  发现了一种使用氧气作为氧化剂的铁催化芳基化反应，可以将杂环化合物与芳香醛进行反应。在氧化条件下，该反应对多种不同底物表现良好。
• KI-catalyzed arylation of benzothiazoles from the coupling of aryl aldehydes with benzothiazoles in neat water
  作者：Yuyu Gao、Qiuling Song、Guolin Cheng、Xiuling Cui

  DOI：10.1039/c3ob42318b

  日期：——

  A KI-catalyzed oxidative coupling of benzothiazoles with aryl aldehydes using TBHP as an oxidant in neat water under metal free conditions is described.

  一种在无金属条件下使用TBHP作为氧化剂，在纯水中，由KI催化的苯并噻唑与芳基醛之间的氧化偶联反应被描述。
• Ligand Combination Approach in Pd‐Catalyzed Direct C−H Arylation of Benzothiazole and Benzoxazole
  作者：Sneha Prasad Bakare、Mahendra Patil

  DOI：10.1002/ejoc.202301013

  日期：2024.1.8

  Two is better than one! A combination of two ligands (Phen.H2O and PPh3) with Pd catalyst offers a highly efficient catalytic system for the direct C−H arylation of benzothiazole and benzoxazole with aryl halides. Mechanistic studies including kinetic isotope effect experiments and computational investigations suggests that two ligands may work cooperatively to enhance the catalytic activity in the

  两个比一个好！两种配体（Phen.H 2 O和PPh 3）与Pd催化剂的组合为苯并噻唑和苯并恶唑与芳基卤化物的直接CH芳基化提供了高效的催化系统。包括动力学同位素效应实验和计算研究在内的机理研究表明，两个配体可能协同作用以增强反应中的催化活性。