methyl 2-[(2-methoxy-2-oxoethyl)thio]benzoate | 6287-88-3

• 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: methyl 2-[(2-methoxy-2-oxoethyl)thio]benzoate
• 英文别名: methyl 2-carbomethoxy-methyl-thio-benzoate；S-Methoxycarbonylmethyl-thiosalicylsaeure-methylester；2-Carbomethoxymethylthio-benzoesaeuremethylester；2-methoxycarbonylmethylsulfanyl-benzoic acid methyl ester；(S-Phenyl-thioglykolsaeuremethylester)-o-carbonsaeuremethylester；[(S-Phenyl-thioglykolsaeure)-o-carbonsaeure]-dimethylester；2-Methoxycarbonylmethylmercapto-benzoesaeure-methylester；Thiosalicylsaeuremethylester-S-essigsaeuremethylester；methyl 2-(2-methoxy-2-oxoethyl)sulfanylbenzoate
• CAS: 6287-88-3
• 化学式: C₁₁H₁₂O₄S
• mdl: MFCD03855443
• 分子量: 240.28
• InChiKey: VXMQJUUBNSATNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2-methoxy-2-oxoethyl)thio]benzoate 在 potassium tert-butylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 24.0h， 生成 3-hydroxy-benzo[b]thiophene-2-carboxylic acid
  参考文献：
  名称：

  Efficient synthesis and 5-LOX/COX-inhibitory activity of some 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives

  摘要：

  A series of 3-hydroxybenzo[b]thiophene-2-carboxylic acid derivatives has been prepared and subsequently evaluated with regards to the inhibition of 5-LOX/COX. Structure optimization furnished derivatives with promising in vitro activity as dual 5-LOX/COX inhibitors with submicromolar IC50 values for inhibition of 5-LOX and COX-1, respectively. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.012
• 作为产物：
  描述：

  o-Carboxybenzenediazonium 在 硫酸 作用下， 生成 methyl 2-[(2-methoxy-2-oxoethyl)thio]benzoate
  参考文献：
  名称：

  Wegscheider; Joachimowitz, Monatshefte fur Chemie, 1914, vol. 35, p. 1046

  摘要：

  DOI：

文献信息

• Application of Magnesium Alkoxides to Syntheses of Benzoheterocyclic Compounds
  作者：Jiří Svoboda、Miloslav Nič、Jaroslav Paleček

  DOI：10.1135/cccc19930592

  日期：——

  The Dieckmann condensation of methyl [(2-methoxycarbonyl)phenyl]-X-acetates Ia-Ih (X = O, S, SO₂, NH, NCH₃) initiated by action of magnesium methoxide, ethoxide, isopropoxide and other basic reagents have been studied under various conditions. Whereas magnesium methoxide has comparable efficiency as sodium methoxide and potassium tert-butoxide in syntheses of benzoheterocyclic compounds IIa-IIh, magnesium ethoxide gives the ethyl ester IIb in medium yield, and magnesium isopropoxide is quite inefficient in the condensation reaction. The alkylation of the esters IIa, IId, and IIg with methyl chloroacetate in the presence of sodium hydride in dimethylformamide gives the diesters IIi - IIk which on action by potassium tert-butoxide undergo the cyclization reaction to give esters III.

  甲基[(2-甲氧羰基)苯基]-X-乙酸酯（X = O，S，SO₂，NH，NCH₃）在镁甲氧基、乙氧基、异丙氧基和其他碱性试剂的作用下进行的Dieckmann缩合反应在各种条件下进行了研究。镁甲氧基在合成苯杂环化合物方面具有与甲基钠和叔丁基钾相当的效率，而镁乙氧基以中等产率给出乙酸乙酯，镁异丙氧基在缩合反应中效率较低。在二甲基甲酰胺中，酯与氯乙酸甲酯在氢化钠存在下发生烷基化反应，得到二酯，经叔丁基钾作用发生环化反应，生成酯。
• Electrosynthesis of Fluorinated Benzo[b]thiophene Derivatives
  作者：Toshio Fuchigami、Bin Yin、Shinsuke Inagi

  DOI：10.1055/s-0030-1260549

  日期：2011.6

  Anodic fluorination of benzo[b]thiophene derivatives provided a complex mixture of di- and trifluorinated products. On the other hand, anodic fluorination of 3-oxo-2,3-dihydrobenzo[b]thiophene and methyl 3-oxo-2,3-dihydrobenzo[b]thiophene-2-carboxylate gave the corresponding monofluorinated products ­selectively in moderate yields. Anodic fluorination of methyl α-(2-cyanophenylthio)acetate followed by intramolecular cyclization provided 3-amino-2-fluorobenzo[b]thiophene in excellent yield.

  苯并[b]噻吩衍生物的阳极氟化反应产生了一种复杂的二氟和三氟混合物。另一方面，3-氧代-2,3-二氢苯并[b]噻吩和 3-氧代-2,3-二氢苯并[b]噻吩-2-甲酸甲酯的阳极氟化反应以中等产率选择性地得到了相应的单氟化产物。对δ-(2-氰基苯硫基)乙酸甲酯进行阳极氟化，然后进行分子内环化，可以得到产率极高的 3-氨基-2-氟苯并[b]噻吩。
• Friedlaender, Chemische Berichte, 1906, vol. 39, p. 1062
  作者：Friedlaender

  DOI：——

  日期：——
• A convenient synthesis of benzothiophene derivatives
  作者：M.Grazia Cabiddu、Salvatore Cabiddu、Enzo Cadoni、Stefania Demontis、Claudia Fattuoni、Stefana Melis

  DOI：10.1016/s0040-4020(02)00399-x

  日期：2002.5

  (Methylthio)- and 2-bromo-1-(methylthio)benzene are useful synthons to prepare monometallated and bimetallated intermediates which lead to 1-benzothiophenes functionalized in the three and/or two positions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• v. Auwers, Justus Liebigs Annalen der Chemie, 1912, vol. 393, p. 358
  作者：v. Auwers

  DOI：——

  日期：——