2-(ethylglyoxyl)benzothiophene | 98800-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(ethylglyoxyl)benzothiophene
• 英文别名: ethyl 2-(benzo[b]thiophen-2-yl)-2-oxoacetate；ethyl-2-oxo-2-(2-benzothienyl)acetate；ethyl 2-(1-benzothiophen-2-yl)-2-oxoacetate
• CAS: 98800-63-6
• 化学式: C₁₂H₁₀O₃S
• 分子量: 234.276
• InChiKey: OQQOAMBJRWQASM-UHFFFAOYSA-N

物化性质

• 沸点：
  367.2±15.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(ethylglyoxyl)benzothiophene 在 palladium on activated charcoal sodium hydroxide 、 甲酸 、 盐酸羟胺 、 氢气 、 sodium acetate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 17.0h， 生成 (6R,7R)-7-(2-Benzo[b]thiophen-2-yl-2-tert-butoxycarbonylamino-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Orally absorbable cephalosporin antibiotics. 1. Structure-activity relationships of benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid

  摘要：

  A structure-activity relationship study of a number of orally absorbed cephalosporins together with their syntheses is described. These new cephalosporins are benzothienyl- and naphthylglycine derivatives of 7-aminodeacetoxycephalosporanic acid. Several different synthetic methods for the glycine side chains, their protection, and the final acylations are reported. Several of these analogues were more active than cephalexin both in vitro and in vivo against commonly encountered Gram-positive bacteria. (R)-7-(3-Benzothienylglycylamido)-3-methyl-3-cephem-4-carboxylic acid (1R) has emerged as a potent antibacterial agent and is currently undergoing preclinical evaluation.

  DOI：

  10.1021/jm00150a022
• 作为产物：
  描述：

  2-乙酰基苯并噻吩 在 吡啶 、 selenium(IV) oxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(ethylglyoxyl)benzothiophene
  参考文献：
  名称：

  单齿瞬态导向基团促进 Pd 催化的 α-酮酯的直接邻 C-H 芳基化和氯化三步合成氯吡格雷外消旋体

  摘要：

  通过使用单齿瞬时导向基团策略和钯催化的组合，成功地实现了 α-酮酯的前所未有的直接邻位C-H 芳基化和氯化。原位形成的亚胺将α-酮酯的双齿配位模式改变为单齿配位，从而实现邻位C-H活化。重要的是，由乙酸根阴离子桥接的关键双核环钯中间体通过 X 射线衍射得到了明确的特征，这有力地支持了所提出的机制。实用性进一步描述为通过随后的两步衍生化轻松获得口服抗血小板药物氯吡格雷消旋体。

  DOI：

  10.1016/j.tet.2022.132980

文献信息

• [EN] GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES<br/>[FR] INHIBITEURS DE LA GLUCOSYLCÉRAMIDE SYNTHASE POUR LE TRAITEMENT DE MALADIES
  申请人：BIOMARIN PHARM INC

  公开号：WO2015042397A1

  公开（公告）日：2015-03-26

  Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

  本文描述了一种I式化合物，制备这种化合物的方法，含有这种化合物的药物组合物和药物，以及使用这种化合物治疗或预防与葡萄糖酰胺合成酶（GCS）相关的疾病或症状的方法。
• .beta.-thiopropionyl-aminoacid derivatives and their use as
  申请人：SmithKline Beecham p.l.c.

  公开号：US06048852A1

  公开（公告）日：2000-04-11

  A method of treatment of bacterial infections in humans or animals which comprises administering, in combination with a .beta.-lactam antibiotic, a therapeutically effective amount of an amino acid derivative of Formula (I) or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof, ##STR1## wherein: R is hydrogen, a salt forming cation or an in vivo hydrolysable ester-forming group; R.sub.1 is hydrogen, (C.sub.1-6)alkyl optionally substituted by up to three halogen atoms or by a mercapto, (C.sub.1-6)alkoxy, hydroxy, amino, nitro, carboxy, (C.sub.1-6)alkylcarbonyloxy, (C.sub.1-6)alkoxycarbonyl, formyl or (C.sub.1-6)alkylcarbonyl group, (C.sub.3-7)cycloalkyl, (C.sub.3-7)cycloalkyl(C.sub.2-6)alkyl, (C.sub.2-6)alkenyl, (C.sub.2-6)alkynyl, aryl, aryl(C.sub.1-6)alkyl, heterocyclyl or heterocyclyl(C.sub.1-6)alkyl; R.sub.2 is hydrogen, (C.sub.1-6)alkyl or aryl(C.sub.1-6)alkyl; R.sub.3 is hydrogen, (C.sub.1-6)alkyl optionally substituted by up to three halogen atoms, (C.sub.3-7)cycloalkyl, fused aryl(C.sub.3-7)cycloalkyl, (C.sub.3-7)cycloalkyl(C.sub.2-6)alkyl, (C.sub.2-6)alkenyl, (C.sub.2-6)alkynyl, aryl, aryl-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n, heterocyclyl or heterocyclyl-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n, where m is 0 to 3, n is 1 to 3, each R.sub.10 and R.sub.11 is independently hydrogen or (C.sub.1-4)alkyl and X is O, S(O).sub.x where x is 0-2, or a bond; R.sub.4 is hydrogen, or an in vivo hydrolysable acyl group; and R.sub.5 and R.sub.6 are independently hydrogen and (C.sub.1-6)alkyl or together represent (CH.sub.2).sub.p where p is 2 to 5. Some compounds are claimed per se.

  一种治疗人类或动物细菌感染的方法，包括与β-内酰胺类抗生素联合给药，给予公式(I)的氨基酸衍生物的治疗有效量或其药用可接受的盐、溶剂化合物或体内可水解酯的治疗有效量，其中：R为氢、形成盐的阳离子或体内可水解酯形成基团；R.sub.1为氢、(C.sub.1-6)烷基，可选地被高达三个卤素原子或巯基、(C.sub.1-6)烷氧基、羟基、氨基、硝基、羧基、(C.sub.1-6)烷基羰氧基、(C.sub.1-6)烷氧羰基、甲酰基或(C.sub.1-6)烷基羰基取代，(C.sub.3-7)环烷基，(C.sub.3-7)环烷基(C.sub.2-6)烷基，(C.sub.2-6)烯基，(C.sub.2-6)炔基，芳基，芳基(C.sub.1-6)烷基，杂环烷基或杂环烷基(C.sub.1-6)烷基；R.sub.2为氢，(C.sub.1-6)烷基或芳基(C.sub.1-6)烷基；R.sub.3为氢，(C.sub.1-6)烷基，可选地被高达三个卤素原子取代，(C.sub.3-7)环烷基，融合的芳基(C.sub.3-7)环烷基，(C.sub.3-7)环烷基(C.sub.2-6)烷基，(C.sub.2-6)烯基，(C.sub.2-6)炔基，芳基，芳基-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n，杂环烷基或杂环烷基-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n，其中m为0至3，n为1至3，每个R.sub.10和R.sub.11独立地为氢或(C.sub.1-4)烷基，X为O，S(O).sub.x，其中x为0-2，或键；R.sub.4为氢，或体内可水解的酰基；R.sub.5和R.sub.6独立地为氢和(C.sub.1-6)烷基，或一起代表(CH.sub.2).sub.p，其中p为2至5。一些化合物本身被要求。
• A New Class of Substituted Aryl Bis(oxazoline) Ligands for Highly Enantioselective Copper-Catalyzed Asymmetric Aldol Addition of Dienolsilane to Pyruvate and Glyoxylate Esters
  作者：Julie Cong-Dung Le、Brian L. Pagenkopf

  DOI：10.1021/ol048179w

  日期：2004.10.1

  [reaction: see text] A new class of bis(oxazoline) ligands are introduced that feature o-alkoxyaryl substituents and provide the highest enantioselectivities yet reported for the copper-catalyzed asymmetric dienosilane aldol addition to pyruvate and glyoxylate esters. Enantioselectivities up to 98% ee (before recrystallization) and isolated yields up to 91% were observed. Additionally, chloride counterions

  [反应：见正文]引入了新型的双（恶唑啉）配体，它们具有邻烷氧基芳基取代基，并提供了除丙酮酸和乙醛酸酯以外的铜催化不对称二烯硅烷醇醛醇缩醛的最高对映选择性。观察到高达98％ee的对映选择性（重结晶之前）和高达91％的分离产率。另外，对于该反应，发现氯离子抗衡离子优于三氟甲磺酸根。
• A General Asymmetric Aldol Reaction of Silyl Ketene Acetals Derived from Simple Esters to Aryl α-Keto Esters
  作者：Julie Le Engers、Brian L. Pagenkopf

  DOI：10.1002/ejoc.200901086

  日期：2009.12

  A general method for the enantioselective addition of O,O-ketene silyl acetals made from simple esters to α-keto esters catalyzed by a CuCl2·bis(oxazoline) complex is reported that overcomes the limitations of the classic aldol reaction, such as steric intolerance and the need for expensive thio esters. This method excels with aryl α-keto esters and provides products in good yield and high ee that

  报道了一种由简单酯制成的 O,O-烯酮甲硅烷基缩醛对映选择性加成到 α-酮酯的通用方法，该方法克服了经典羟醛反应的局限性，如空间不耐受以及需要昂贵的硫代酯。该方法在处理芳基 α-酮酯方面表现出色，可提供高产率和高 ee 的产品，这是替代策略不容易获得的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Synthesis of Sterically Hindered α-Hydroxycarbonyls through Radical–Radical Coupling
  作者：Kenji Ota、Kazunori Nagao、Hirohisa Ohmiya

  DOI：10.1021/acs.orglett.1c01358

  日期：2021.6.4

  describe a synthetic approach to sterically hindered α-hydroxy carbonyl compounds through radical–radical coupling. An organic photoredox catalysis reaction converts an aliphatic carboxylic acid and α-ketocarbonyl to a transient alkyl radical and a persistent ketyl radical, respectively, which couple selectively based on the persistent radical effect. This protocol allows the use of primary, secondary, and

  我们描述了一种通过自由基-自由基偶联合成位阻α-羟基羰基化合物的方法。有机光氧化还原催化反应将脂肪族羧酸和α-酮羰基分别转化为瞬态烷基和持久性羰基自由基，它们基于持久性自由基效应选择性地偶联。该协议允许使用一级、二级和三级脂肪族羧酸在温和的反应条件下将各种烷基取代基引入 α-ketocarbonyls 的酮部分。