2-chloro-1-(thiophen-3-yl)ethan-1-one | 50460-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-1-(thiophen-3-yl)ethan-1-one
• 英文别名: thien-3-yl chloromethyl ketone；2-chloro-1-thiophen-3-ylethanone
• CAS: 50460-10-1
• 化学式: C₆H₅ClOS
• 分子量: 160.624
• InChiKey: DUVRDRIDUGKOHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-1-(thiophen-3-yl)ethan-1-one 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 (1S,2S)-(+)-N-对甲苯磺酰基-1,2-二苯基乙二胺 甲酸 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 Methyl-carbamic acid (R)-2-chloro-1-thiophen-3-yl-ethyl ester
  参考文献：
  名称：

  Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols

  摘要：

  As part of medicinal chemistry efforts we found it necessary to develop general syntheses of highly enantiomerically enriched 1-aryl-2-chloroethanols and 1-aryl-2-methylaminoethanols. A survey of literature methods suggested that a truly general approach had not yet been reported, encouraging us to undertake the development of such a methodology. This study describes the design, development, and reduction to practice of a general synthesis of chiral 1-aryl-2-chloroethanols and the transformation of these entities to highly enantiomerically enriched 1-aryl-2-methylaminoethanols. Of particular importance were observations of the impact of solvent and the method of catalyst preparation on the yield and enantiomerical excess of chlorohydrins prepared via Noyori transfer hydrogenations of aryl-chloromethyl ketones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.017
• 作为产物：
  描述：

  3-乙酰基噻吩 在 N,N,N-trimethylbenzenemethanaminium dichloroiodate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2-chloro-1-(thiophen-3-yl)ethan-1-one
  参考文献：
  名称：

  Enantioselective synthesis of heteroaromatic epoxyketones under phase-transfer catalysis using d-glucose- and d-mannose-based crown ethers

  摘要：

  Heteroaromatic epoxyketones have been synthesized in an asymmetric Darzens condensation of 2-chloroacetylfuran or 2- and 3-chloroacetylthiophene with aromatic aldehydes and in the enantioselective epoxidation of alpha,beta-enones with an N-methylpyrrole unit, in both cases in the presence of D-glucose- 1 or D-mannose-based 2 crown ethers as phase transfer catalysts. The use of D-glucose-based 1 lariat ether as the catalyst gave the best results. The alpha,beta-epoxyketones with a furan or a thiophene moiety were obtained in good enantioselectivities (up to 86% ee) as well as excellent diastereoselectivities (up to 98:2), but the epoxyketones with a pyrrole-ring were formed in the Darzens condensation in low yields and enantioselectivities. The epoxyketones with an N-methylpyrrole moiety isolated from the epoxidation of the corresponding alpha,beta-enones were obtained in significant enantioselectivities (in ee values up to 81%) in the presence of catalyst 1 under mild reaction conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.001

文献信息

• An efficient heterogeneous gold(I)-catalyzed hydration of haloalkynes leading to α-halomethyl ketones
  作者：Sifan Hu、Dayi Liu、Chenyu Yan、Mingzhong Cai

  DOI：10.1080/00397911.2018.1528616

  日期：2018.12.2

  Abstract A highly efficient heterogeneous gold(I)-catalyzed hydration of haloalkynes has been developed that proceeds smoothly under mild and neutral conditions and provides a general and practical route for the synthesis of a variety of α-halomethyl ketones with high atom-economy, excellent yield, and recyclability of the gold(I) catalyst. The presented method delivers an attractive alternative to

  摘要 开发了一种高效的多相金（I）催化卤代炔烃的水合反应，在温和、中性条件下顺利进行，为合成多种高原子经济性、优异的α-卤代甲基酮提供了一条通用实用的途径。金（I）催化剂的产率和可回收性。所提出的方法为酮的经典 α-卤化提供了一种有吸引力的替代方法。图形概要
• Pyridoquinoxaline antivirals
  申请人：——

  公开号：US20030207877A1

  公开（公告）日：2003-11-06

  The present invention provides a compound of formula I 1 or a pharmaceutically acceptable salt thereof wherein R 1 , R 2 and R 3 are as defined in the specification. The compounds are useful for the treatment of viral infections.

  本发明提供了一种具有以下结构的化合物I或其药学上可接受的盐，其中R1、R2和R3如规范中定义。这些化合物对于治疗病毒感染是有用的。
• SUBSTITUTED PYRAZOLO[4,3-b]PYRIDINES AND THEIR USE AS GLUN2B RECEPTOR MODULATORS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：US20200392130A1

  公开（公告）日：2020-12-17

  Substituted pyrazolo[4,3-b]pyridines as GluN2B receptor ligands. Such compounds may be used in GluN2B receptor modulation and in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by GluN2B receptor activity.

  取代的吡唑并[4,3-b]吡啶作为GluN2B受体配体。这类化合物可用于GluN2B受体调节，以及用于治疗由GluN2B受体活性介导的疾病状态、疾病和症状的药物组合物和方法。
• [EN] SUBSTITUTED PYRAZOLO[4,3-b]PYRIDINES AND THEIR USE AS GLUN2B RECEPTOR MODULATORS<br/>[FR] PYRAZOLO[4,3-B]PYRIDINES SUBSTITUÉES ET LEUR UTILISATION EN TANT QUE MODULATEURS DU RÉCEPTEUR GLUN2B
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2020249791A1

  公开（公告）日：2020-12-17

  Substituted pyrazolo[4,3-b]pyridines as GluN2B receptor ligands. Such compounds may be used in GluN2B receptor modulation and in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by GluN2B receptor activity.

  取代的吡唑[4,3-b]吡啶作为GluN2B受体配体。这些化合物可用于GluN2B受体调节以及用于治疗由GluN2B受体活性介导的疾病状态、疾病和疾病的制药组合物和方法。
• Thiazolylaminomannosides As Potent Antiadhesives of Type 1 Piliated Escherichia coli Isolated from Crohn’s Disease Patients
  作者：Sami Brument、Adeline Sivignon、Tetiana I. Dumych、Nicolas Moreau、Goedele Roos、Yann Guérardel、Thibaut Chalopin、David Deniaud、Rostyslav O. Bilyy、Arlette Darfeuille-Michaud、Julie Bouckaert、Sébastien G. Gouin

  DOI：10.1021/jm400723n

  日期：2013.7.11

  Adherent-invasive Escherichia coli (AIEC) have previously been shown to induce gut inflammation in patients with Crohn’s disease (CD). We developed a set of mannosides to prevent AIEC attachment to the gut by blocking the FimH bacterial adhesin. The crystal structure of the FimH lectin domain in complex with a lead thiazolylaminomannoside highlighted the preferential position for pharmacomodulations

  粘附侵袭性大肠杆菌先前已证明（AIEC）可以诱发克罗恩病（CD）患者的肠道炎症。我们开发了一组甘露糖苷，通过阻断FimH细菌粘附素来防止​​AIEC附着在肠道上。FimH凝集素结构域与噻唑基氨基甘露糖苷铅复合的晶体结构突出显示了药物调制的优先位置。然后建立了一个小型的类似物库，该库显示出对FimH具有纳摩尔浓度的亲和力。值得注意的是，活性最高的化合物可有效防止AIEC附着于肠细胞，其浓度分别比甘露糖和强效FimH抑制剂庚基甘露糖苷低约10000倍和100倍。在CD转基因小鼠模型的结肠组织上进行的离体测定证实了这种抗粘连的潜力。