2-[(氰基甲基)磺酰基]苯甲酸甲酯 | 175137-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[(氰基甲基)磺酰基]苯甲酸甲酯
• 英文名称: mekthyl 2-(cyanomethylsulfonyl)benzoate
• 英文别名: methyl 2-((cyanomethyl)sulfonyl)benzoate；Methyl 2-[(cyanomethyl)sulfonyl]benzoate；methyl 2-(cyanomethylsulfonyl)benzoate
• CAS: 175137-52-7
• 化学式: C₁₀H₉NO₄S
• mdl: MFCD00068077
• 分子量: 239.252
• InChiKey: GSBCUUXSBJVYLU-UHFFFAOYSA-N

物化性质

• 沸点：
  473.9±45.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92.6
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-[(氰基甲基)磺酰基]苯甲酸甲酯 在 potassium tert-butylate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 17.5h， 生成 10,10-dioxo-4H-thieno[3,2-b][1,4]benzothiazepin-5-one
  参考文献：
  名称：

  Synthesis and antiviral/antitumor evaluation of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes and related compounds as a new class of diarylsulfones

  摘要：

  Based on general SARs previously described for anti-HIV-l diarylsulfone derivatives, a series of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes has been prepared and evaluated as potential antiviral and antitumor agents. In cell culture, some of the 2-aminothiophenes exhibited moderate and selective activity against HIV-1, with 2-amino-3-(2-nitrophenylsulfonyl)thiophene (7e) being most attractive (EC50 = 3.8 mug/mL: CC50 = > 100 mug/mL). In broad-spectrum antiviral assays, the 3-arylsulfonyl-2-(trifluoroacetamido)thio (8c-g) and 2-acetamido-3-arylsulfonyl-5-nitrothiophenes (9f-g) proved considerably active (IC50 = 0.1-10 mug/mL) against human cytomegalovirus (CMV) and/or varicella tester virus (VZV). Based on the activity of the trifluoroacetamides, ring-modified furan, N-(substituted)pyrrole, phenyl, and 3,4-thiophene analogues were prepared, and these compounds were also active against CMV and/or VZV, with the notable exception of the 3,4-thiophene derivative. In contrast to other amines, the 2-aminopyrrole precursors (13a-d) also exhibited potent activity against CMV. Unfortunately, most of these compounds displayed significant cytotoxicity against human fibroblasts, the cells supporting CMV and VZV replication, and thus selectivity indices were low. The most notable exception to this was the naphthyl-substituted aminopyrrole 13d, which exhibited both potent (IC50 = 0.3 mug/mL) and selective (CC50 = > 50 mug/mL) activity against CMV. Finally, thiophene aryl amides 8i-k displayed moderate in vitro activity against certain leukemia, breast, and colon cancer cell lines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00333-3
• 作为产物：
  描述：

  2-(氰基甲硫基)苯甲酸 在 氯化亚砜 、 双氧水 、 溶剂黄146 作用下， 反应 8.75h， 生成 2-[(氰基甲基)磺酰基]苯甲酸甲酯
  参考文献：
  名称：

  由3-烷氧基-2-芳基（或甲基）-磺酰基丙烯腈合成3-氨基-4-芳基（或甲基）磺酰基-2-噻吩羧酸甲酯

  摘要：

  描述了在三乙胺存在下，通过3-烷氧基-2-芳基（或甲基）磺酰基丙烯腈与硫代乙醇酸甲酯的反应，合成一系列3-氨基-4-芳基（或甲基）磺酰基噻吩-2-羧酸甲酯。酯在2-位的水解/脱羧和所得胺的酰化代表了形成4-芳基磺酰基-3-羧酰胺基噻吩的便利途径。在标准条件下尝试酰化标题氨基噻吩未成功。

  DOI：

  10.1002/jhet.5570360314

文献信息

• Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation
  作者：Kaida Zhou、Jin-Biao Liu、Wenlin Xie、Shengqing Ye、Jie Wu

  DOI：10.1039/d0cc00351d

  日期：——

  3-azido-2-methylbut-3-en-2-ol under ultraviolet irradiation at room temperature is achieved, giving rise to 2-(arylsulfonyl)acetonitriles in moderate to good yields. Alkyl iodide is also workable under these conditions. This transformation proceeds smoothly under mild conditions with a broad substrate scope. Various functional groups are compatible including amino, ester, halo, and trifluoromethyl groups. No metal catalyst

  在室温下紫外线照射下，二氧化硫与芳基碘化物和3-叠氮基-2-甲基丁-3-烯-2-醇的无金属插入得以实现，从而以中等至良好的产率产生了2-（芳基磺酰基）乙腈。烷基碘化物在这些条件下也是可行的。该转化在温和条件下在宽范围的底物范围内平稳进行。各种官能团相容，包括氨基，酯，卤素和三氟甲基。在反应过程中不需要金属催化剂或添加剂。机理研究表明，在紫外线照射下，碘化芳基会原位生成芳基，然后通过插入二氧化硫进行芳基磺酰化，生成芳基磺酰基自由基中间体。
• Synthesis of methyl 3-amino-4-aryl(or methyl)sulfonyl-2-thiophenecarboxylates from 3-alkoxy-2-aryl(or methyl)-sulfonylacrylonitriles
  作者：Chad E. Stephens、Matthew B. Price、J. Walter Sowell

  DOI：10.1002/jhet.5570360314

  日期：1999.5

  The synthesis of a series of methyl 3-amino-4-aryl(or methyl)sulfonylthiophene-2-carboxylates by reaction of 3-alkoxy-2-aryI(or methyl)sulfonylacrylonitriles with methyl thioglycolate in the presence of triethylamine is described. Hydrolysis/decarboxylation of the ester at the 2-position and acylation of the resulting amine represents a convenient route to 4-arylsulfonyl-3-carboxamidothiophenes. Attempted

  描述了在三乙胺存在下，通过3-烷氧基-2-芳基（或甲基）磺酰基丙烯腈与硫代乙醇酸甲酯的反应，合成一系列3-氨基-4-芳基（或甲基）磺酰基噻吩-2-羧酸甲酯。酯在2-位的水解/脱羧和所得胺的酰化代表了形成4-芳基磺酰基-3-羧酰胺基噻吩的便利途径。在标准条件下尝试酰化标题氨基噻吩未成功。
• Synthesis and antiviral/antitumor evaluation of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes and related compounds as a new class of diarylsulfones
  作者：C Stephens

  DOI：10.1016/s0968-0896(00)00333-3

  日期：2001.5

  Based on general SARs previously described for anti-HIV-l diarylsulfone derivatives, a series of 2-amino- and 2-carboxamido-3-arylsulfonylthiophenes has been prepared and evaluated as potential antiviral and antitumor agents. In cell culture, some of the 2-aminothiophenes exhibited moderate and selective activity against HIV-1, with 2-amino-3-(2-nitrophenylsulfonyl)thiophene (7e) being most attractive (EC50 = 3.8 mug/mL: CC50 = > 100 mug/mL). In broad-spectrum antiviral assays, the 3-arylsulfonyl-2-(trifluoroacetamido)thio (8c-g) and 2-acetamido-3-arylsulfonyl-5-nitrothiophenes (9f-g) proved considerably active (IC50 = 0.1-10 mug/mL) against human cytomegalovirus (CMV) and/or varicella tester virus (VZV). Based on the activity of the trifluoroacetamides, ring-modified furan, N-(substituted)pyrrole, phenyl, and 3,4-thiophene analogues were prepared, and these compounds were also active against CMV and/or VZV, with the notable exception of the 3,4-thiophene derivative. In contrast to other amines, the 2-aminopyrrole precursors (13a-d) also exhibited potent activity against CMV. Unfortunately, most of these compounds displayed significant cytotoxicity against human fibroblasts, the cells supporting CMV and VZV replication, and thus selectivity indices were low. The most notable exception to this was the naphthyl-substituted aminopyrrole 13d, which exhibited both potent (IC50 = 0.3 mug/mL) and selective (CC50 = > 50 mug/mL) activity against CMV. Finally, thiophene aryl amides 8i-k displayed moderate in vitro activity against certain leukemia, breast, and colon cancer cell lines. (C) 2001 Elsevier Science Ltd. All rights reserved.

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