ethyl 2-(5-acetylthiophen-2-yl)acetate | 342422-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(5-acetylthiophen-2-yl)acetate
• 英文别名: ethyl 5-acetylthiophene-2-acetate；5-Acetyl-2-thiopheneacetic acid ethyl ester
• CAS: 342422-46-2
• 化学式: C₁₀H₁₂O₃S
• mdl: MFCD30290431
• 分子量: 212.269
• InChiKey: KRJBLQSIRBRBES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  ethyl 2-(5-acetylthiophen-2-yl)acetate 在 三乙基硅烷 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Design, synthesis and evaluation of benzo[a]thieno[3,2-g]quinolizines as novel l-SPD derivatives possessing dopamine D1, D2 and serotonin 5-HT1A multiple action profiles

  摘要：

  A novel scaffold derived from l-SPD with a substituted thiophene group in the D ring were designed, synthesized, and evaluated for their binding affinities at dopamine (D-1, D-2 and D-3) and serotonin (5-HT1A and 5-HT2A) receptors. Most of the tetracyclic compounds exhibited higher affinities for D-2 and 5-HT1A receptors than l-SPD, while compound 23e showed the highest K-i value of 7.54 nM at D-2 receptor which was 14 times more potent than l-SPD. Additionally, compounds 23d and 23e were more potent than l-SPD at D-3 receptor. According to the functional assays, 23d and 23e were demonstrated as full antagonists at D-1 and D-2 receptors and full agonists at 5-HT1A receptor. Since the combination of D-2 antagonism and 5-HT1A agonism is considered effective in treating both the positive and negative symptoms of schizophrenia, these novel compounds are implicated as potential therapeutic agents. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.09.024
• 作为产物：
  描述：

  5-乙酰基-2-噻吩硼酸 在 potassium fluoride 、 (三氟甲基)三甲基硅烷 、 三氟乙酸 作用下， 以 乙二醇二甲醚 为溶剂， 反应 20.58h， 生成 ethyl 2-(5-acetylthiophen-2-yl)acetate
  参考文献：
  名称：

  Reactions of CF3-substituted boranes with α-diazocarbonyl compounds

  摘要：

  Boranes substituted with a CF3-group can be generated from methyl boronic esters RB(OMe)(2) and Me3SiCF3/KF followed by treatment with Me3SiCl. These boranes are stable only in coordinating solvents, and due to the increased Lewis acidity of boron, react rapidly with alpha-diazocarbonyl compounds to give the products of transfer of the organic group from boron. Alkyl, aryl, vinyl, and alkynyl boronic esters can be used in this reaction. (C) 2011 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tetlet.2011.07.141

文献信息

• Organo-photoredox-Catalyzed Selective Mono- and Bis-C–H Alkylation of Electron-Rich (Hetero)Arenes
  作者：Shyamal Pramanik、Partha Pratim Mondal、Soumitra Maity

  DOI：10.1021/acs.joc.3c01757

  日期：2023.11.3

  under mild conditions. The extent of alkylation with alkyl bromides was found to be controlled by introducing Zn(OAc)2 as a bromide scavenger, ensuring the blocking of potential bromo-arene byproduct formation under photoredox conditions. In addition, a sequential C–H alkylation strategy for selective bis-alkylation has also been developed via chronological incorporation of different alkyl radical precursors

  在此，我们公开了一种利用可见光介导的有机光催化SET过程用烷基​​溴对富电子（杂）芳烃进行C-H烷基化的简单策略。该方法的通用性已通过在温和条件下包含各种烷基（α-烷基羰基、苄基、氰甲基）以及各种具有生物活性的富电子芳烃和（杂）芳烃得到证明。发现用烷基溴进行烷基化的程度可以通过引入Zn(OAc) 2作为溴化物清除剂来控制，确保阻止光氧化还原条件下潜在的溴代芳烃副产物的形成。此外，通过按时间顺序将不同的烷基自由基前体在一锅中相当有效地结合，还开发了用于选择性双烷基化的顺序C-H烷基化策略。
• DIARYL[A, G]QUINOLIZIDINE COMPOUND, PREPARATION METHOD THEREFOR, PHARMACEUTICAL COMPOSITION, AND USES THEREOF
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP2848617B1

  公开（公告）日：2022-01-12
• MAILLARD J.; LANGLOIS M.; DELAUNAY P.; VAN TRI VO; MEINGAN J.-P.; RAPIN M+, EUR. I. MED. CHEM., 1977,
  作者：MAILLARD J.、 LANGLOIS M.、 DELAUNAY P.、 VAN TRI VO、 MEINGAN J.-P.、 RAPIN M+

  DOI：——

  日期：——
• US9751882B2
  申请人：——

  公开号：US9751882B2

  公开（公告）日：2017-09-05
• Reactions of CF3-substituted boranes with α-diazocarbonyl compounds
  作者：Pavel K. Elkin、Vitalij V. Levin、Alexander D. Dilman、Marina I. Struchkova、Pavel A. Belyakov、Dmitry E. Arkhipov、Alexander A. Korlyukov、Vladimir A. Tartakovsky

  DOI：10.1016/j.tetlet.2011.07.141

  日期：2011.10

  Boranes substituted with a CF3-group can be generated from methyl boronic esters RB(OMe)(2) and Me3SiCF3/KF followed by treatment with Me3SiCl. These boranes are stable only in coordinating solvents, and due to the increased Lewis acidity of boron, react rapidly with alpha-diazocarbonyl compounds to give the products of transfer of the organic group from boron. Alkyl, aryl, vinyl, and alkynyl boronic esters can be used in this reaction. (C) 2011 Elsevier Ltd. All rights reserved,