1-(furan-2-yl)-2-thiocyanatoethan-1-one | 200621-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(furan-2-yl)-2-thiocyanatoethan-1-one
• 英文别名: 2-(Furan-2-yl)-2-oxoethyl thiocyanate；[2-(furan-2-yl)-2-oxoethyl] thiocyanate
• CAS: 200621-67-6
• 化学式: C₇H₅NO₂S
• 分子量: 167.188
• InChiKey: FMDGNCTUJUYADU-UHFFFAOYSA-N

物化性质

• 熔点：
  101-103 °C
• 沸点：
  331.6±22.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(furan-2-yl)-2-thiocyanatoethan-1-one 在 copper(l) iodide 、 sodium azide 、 氢溴酸 、 溶剂黄146 、 N,N'-二甲基乙二胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(4-(furan-2-yl)thiazol-2-yl)-4-(thiophen-2-yl)-1H-1,2,3-triazole
  参考文献：
  名称：

  One-Pot Tandem Copper-Catalyzed Library Synthesis of 1-Thiazolyl-1,2,3-triazoles as Anticancer Agents

  摘要：

  One-pot multicomponent synthesis to assemble compounds has been an efficient method for constructing a compound library. We have developed one-pot tandem copper-catalyzed azidation and CuAAC reactions that afford 1-thiazolyl-1,2,3-triazoles with anticancer activity. By utilizing this one-pot synthetic strategy, we constructed a library of 1-thiazolyl-1,2,3-triazoles in search of the potent lead compound. Furthermore, 1-thiazolyl-1,2,3-triazoles were evaluated for anticancer activity against the multidrug-resistant cancer cells MES-SA/Dx5. Most of the 1-thiazolyl-1,2,3-triazoles revealed cytotoxic effect against cancer cells at micromolar to low micromolar range. Testing some of the most potent compounds (5{4,2-4} and 5{5,1-3}) against the normal cell line Vero showed no significant toxicity (except 5{4,2}) to normal cells. This result indicates that compounds 5{4,3-4} and 5{5,1-3} possessed good potency and selectivity to cancer cells over normal cells.

  DOI：

  10.1021/co1000234
• 作为产物：
  描述：

  2-乙酰基呋喃 在 溴 作用下， 以 1,4-二氧六环 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(furan-2-yl)-2-thiocyanatoethan-1-one
  参考文献：
  名称：

  One-Pot Tandem Copper-Catalyzed Library Synthesis of 1-Thiazolyl-1,2,3-triazoles as Anticancer Agents

  摘要：

  One-pot multicomponent synthesis to assemble compounds has been an efficient method for constructing a compound library. We have developed one-pot tandem copper-catalyzed azidation and CuAAC reactions that afford 1-thiazolyl-1,2,3-triazoles with anticancer activity. By utilizing this one-pot synthetic strategy, we constructed a library of 1-thiazolyl-1,2,3-triazoles in search of the potent lead compound. Furthermore, 1-thiazolyl-1,2,3-triazoles were evaluated for anticancer activity against the multidrug-resistant cancer cells MES-SA/Dx5. Most of the 1-thiazolyl-1,2,3-triazoles revealed cytotoxic effect against cancer cells at micromolar to low micromolar range. Testing some of the most potent compounds (5{4,2-4} and 5{5,1-3}) against the normal cell line Vero showed no significant toxicity (except 5{4,2}) to normal cells. This result indicates that compounds 5{4,3-4} and 5{5,1-3} possessed good potency and selectivity to cancer cells over normal cells.

  DOI：

  10.1021/co1000234

文献信息

• α-Thiocyanation of Carbonyl and β-Dicarbonyl Compounds Using (Dichloroiodo)benzene−Lead(II) Thiocyanate
  作者：Om Prakash、Harpreet Kaur、Hitesh Batra、Neena Rani、Shiv P. Singh、Robert M. Moriarty

  DOI：10.1021/jo001504i

  日期：2001.3.1

  combination reagent (dichloroiodo)benzene and lead(II) thiocyanate in dichloromethane effects oxidation of various enol silyl ethers, ketene silyl acetals, and beta-dicarbonyl compounds, thereby providing an efficient and convenient method for alpha-thiocyanation of carbonyl and beta-dicarbonyl compounds.

  二氯甲烷中的（二氯碘代）苯和硫氰酸铅（II）的组合试剂可实现各种烯醇甲硅烷基醚，乙烯酮甲硅烷基乙缩醛和β-二羰基化合物的氧化，从而为羰基和β-二羰基的α-硫氰化提供了一种有效而便捷的方法化合物。
• Hypervalent Iodine(III) Sulfonate Mediated Synthesis of α-Thiocynanatoketones in a Task-Specific Ionic Liquid [bmim]SCN
  作者：Hsin-Yu Huang、Huey-Min Wang、Rei-Sheu Hou、Hui-Ting Cheng、Ling-Ching Chen

  DOI：10.1002/jccs.200800179

  日期：2008.12

  The task-specific ionic liquid (TSIL) and 1-n-butyl-3-methylimidazolium thiocynanate, ([bmim]SCN) were used as the medium as well as the reactant for the synthesis of α-thiocynanatoketones by the reaction with α-sulfonyloxy aryl ketones. Significant rate enhancements and improved yields have been observed.

  任务特异性离子液体 (TSIL) 和 1-n-丁基-3-甲基咪唑硫氰酸酯 ([bmim]SCN) 用作介质以及通过与 α- 反应合成 α-硫氰酸酮的反应物磺酰氧基芳基酮。已经观察到显着的速率提高和提高的产量。
• α-Thiocyanation of Ketones and Esters Using (Dichloroiodo)benzene-Lead(II) Thiocyanate
  作者：Om Prakash、Neena Rani、Vijay Sharma、Robert Moriarty

  DOI：10.1055/s-1997-1027

  日期：1997.11

  Reaction of enol silyl ethers of acetophenone, 2-acetylfuran, 2-acetylthiophene, 2-acetylpyridine, cyclopentanone and cyclohexanone, and ketene silyl acetals of arylacetic esters with a combination of lead(II) thiocyanate and (dichloroiodo)benzene affords the corresponding α-thiocyanated ketones and esters.

  将苯乙酮、2-乙酰基呋喃、2-乙酰基噻吩、2-乙酰基吡啶、环戊酮和环己酮的烯醇硅醚以及芳基乙酸酯的酮硅基乙醛与硫氰酸铅（II）和（二氯碘）苯反应，可得到相应的δ-硫氰酸化酮和酯。
• THIAZOLE DERIVATIVES
  申请人：Sugawara Masamori

  公开号：US20100280023A1

  公开（公告）日：2010-11-04

  It is intended to provide an adenosine A 2A receptor antagonist containing as an active ingredient a thiazole derivative represented by the general formula (I) [in the formula, R 1 represents a substituted or unsubstituted five-membered aromatic heterocyclic group containing at least one oxygen atom, R 2 represents a substituted or unsubstituted heterocyclic group, —COR 6 (in the formula, R 6 represents a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aromatic heterocyclic group or the like) or the like, R 3 represents the general formula (II), —NHCOR (in the formula, R 7 represents —NR 8 R 9 or the like) or the like], or a pharmacologically acceptable salt thereof, etc. (I) (II)

  该药品旨在提供一种含有腺苷A2A受体拮抗剂的活性成分，该成分为通式（I）所代表的噻唑衍生物[在公式中，R1代表含有至少一个氧原子的取代或未取代的五元芳香杂环基，R2代表取代或未取代的杂环基，-COR6(在公式中，R6代表取代或未取代的杂环基、取代或未取代的芳香杂环基或类似物)或类似物，R3代表通式（II），-NHCOR (在公式中，R7代表-NR8R9或类似物)或类似物]，或其药理学上可接受的盐等。(I) (II)
• THERAPEUTIC AND/OR PREVENTIVE AGENTS FOR A SLEEP DISORDER
  申请人：Uesaka Noriaki

  公开号：US20100152162A1

  公开（公告）日：2010-06-17

  It is intended to provide an agent for treating and/or preventing sleep disorder containing as an active ingredient a thiazole derivative represented by the general formula (I) (in the formula, R 1 represents a five-membered aromatic heterocyclic group containing at least one oxygen atom or the like, R 2 represents halogen or the like, and R 3 represents —NR 10 R 11 (in the formula, R 10 and R 11 are the same or different and represent a hydrogen atom or the like) or the like) or a pharmacologically acceptable salt thereof.

  该发明旨在提供一种治疗和/或预防睡眠障碍的药剂，其活性成分为一种由通式（I）表示的噻唑衍生物（在公式中，R1表示至少含有一个氧原子的五元芳香杂环基团或类似基团，R2表示卤素或类似基团，R3表示-NR10R11（在公式中，R10和R11相同或不同，表示氢原子或类似基团）或类似基团）或其药理学上可接受的盐。