2-thiophenecarbothioic acid O-ethyl ester | 13749-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-thiophenecarbothioic acid O-ethyl ester
• 英文别名: thiophene-2-carbothioic acid O-ethyl ester；2-Thiophenecarbothioic acid, O-ethyl ester；O-ethyl thiophene-2-carbothioate
• CAS: 13749-76-3
• 化学式: C₇H₈OS₂
• 分子量: 172.272
• InChiKey: APLVEDADPXPMGB-UHFFFAOYSA-N

物化性质

• 沸点：
  230.0±32.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-thiophenecarbothioic acid O-ethyl ester 在 镍 作用下， 以 乙醚 为溶剂， 生成 戊基乙基醚
  参考文献：
  名称：

  A new conversion of esters to ethers and its application to the preparation of furano-18-crown-6

  摘要：

  DOI：

  10.1021/jo00317a045
• 作为产物：
  描述：

  2-噻吩羧酸乙酯 在 劳森试剂 作用下， 反应 0.05h， 以89%的产率得到2-thiophenecarbothioic acid O-ethyl ester
  参考文献：
  名称：

  Microwave-Accelerated Solvent-Free Synthesis of Thioketones, Thiolactones, Thioamides, Thionoesters, and Thioflavonoids

  摘要：

  [GRAPHICS]An expeditious, solvent free, and high yield conversion of ketones, flavones, isoflavones, lactones, amides, and esters to the corresponding thio analogues is described utilizing Lawesson's reagent in a process that circumvents the use of dry solvents and excess of the reagent.

  DOI：

  10.1021/ol990629a

文献信息

• Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters
  作者：Tomoya Miura、Yuuta Funakoshi、Yoshikazu Fujimoto、Junki Nakahashi、Masahiro Murakami

  DOI：10.1021/acs.orglett.5b00960

  日期：2015.5.15

  A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with thionoesters in the presence of a rhodium(II) catalyst. The resulting 3-sulfonyl-4-thiazolines subsequently aromatize

  据报道从末端炔烃，磺酰基叠氮化物和硫代磺酸酯合成2，5-二取代的噻唑的顺序方法。末端炔烃与磺酰基叠氮化物的铜（I）催化的1,3-偶极环加成反应生成1-磺酰基-1,2,3-三唑，然后在铑（II）催化剂存在下与硫磺酸酯反应。随后通过消除磺酰基基团将所得的3-磺酰基-4-噻唑啉芳香化为相应的2，5-二取代的噻唑。
• A Short Synthesis of 2,3-Di(hetero)arylpyrido[3,2-f]thiazepines
  作者：Axel Couture、Eric Deniau、Pierre Grandclaudon、Cristian Simion

  DOI：10.1055/s-1996-4329

  日期：1996.8

  A reaction sequence leading to the new title compounds is described, the key step of which is the treatment of anions of N-arylmethyl(2-chloropyridyl) methylidene amines with aromatic and heteroaromatic O-ethyl thiocarboxylates.

  描述了一种导致新标题化合物的反应序列，其中关键步骤是使用芳香族和杂芳香族O-ethyl硫代羧酸酯处理N-芳基甲基（2-氯吡啶基）亚胺的阴离子。
• A Facile and Concise Synthesis of 2-Alkyl- and 2-Aryl-4-oxo- 4<i>H</i>thiopyrano[2,3-<i>b</i>]pyridines
  作者：Axel Couture、Pierre Grandclaudon、Eric Huguerre

  DOI：10.1055/s-1989-27288

  日期：——

  2-Alkyl- and 2-aryl-4-oxo-4H-thiopyrano[2,3-b]pyridine can be conveniently prepared by reacting the appropriate aromatic and aliphatic O-ethyl thiocarboxylates with the sodium derivative of various alkyl 3-(2-bromopyridyl) ketones.

  2-烷基和2-芳基-4-氧代-4H-噻吡啶[2,3-b]吡啶可通过与适当的芳香和脂肪族O-乙基硫代羧酸酯反应，制备得到各种烷基3-(2-溴吡啶基)酮的钠衍生物，从而方便地合成。
• A New and Concise Synthesis of 3-Aryl- and 3-Alkyl-1<i>H</i>-2-benzothiopyran-1-ones (Thioisocoumarins)
  作者：Axel Couture、Hélène Cornet、Pierre Grandclaudon

  DOI：10.1055/s-1990-27113

  日期：——

  3-Aryl- and 3-alkyl-1H-2-benzothiopyran-1-ones are readily accessible by reaction of the lithiated N,N-diethyl-o-toluamide (N,N-diethyl-2-methylbenzenecarboxamide) with appropriate aromatic, heteroaromatic and aliphatic thioesters.

  3-芳基和3-烷基-1H-2-苯并噻吩-1-酮可以通过锂化的N,N-二乙基邻甲苯酰胺（N,N-二乙基-2-甲基苯甲酰胺）与合适的芳香、杂芳香和脂肪族硫酯反应制备。
• Simple Preparation of Polyhydro-6-aryl(heteroaryl)cycloalka[<i>b</i>][1,5]naphthyridines
  作者：Axel Couture、Eric Deniau、Pierre Grandclaudon、Cristian Simion

  DOI：10.1055/s-1993-26030

  日期：——

  A variety of polyhydro-6-aryl- and heteroarylcycloalka[b][1,5] naphthyridines have been efficiently prepared by thermally induced ring contraction of pyrido[2,3-b][1,5]thiazepines obtained by reacting lithiated 2-chloro-N-cycloalkylidene-3-pyridinimines with suitable O-ethyl thiocarboxylates.

  各种多氢-6-芳基-和杂芳基环烷[b][1,5]萘啶已通过热诱导环收缩有效地制备了通过锂化2-反应获得的吡啶并[2,3-b][1,5]硫氮杂卓类化合物。氯-N-亚环烷基-3-吡啶亚胺与合适的O-硫代羧酸乙酯。