3-cyanothiobenzamide | 78950-37-5

• 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: 3-cyanothiobenzamide
• 英文别名: m-cyanothiobenzamide；3-Cyanobenzene-1-carbothioamide；3-cyanobenzenecarbothioamide
• CAS: 78950-37-5
• 化学式: C₈H₆N₂S
• mdl: MFCD09863882
• 分子量: 162.215
• InChiKey: SUNZSUISYUKMAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyanothiobenzamide 在 吡啶 、 ammonium sulfide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 3-[5-(4-bromophenyl)-4-hydroxythiazol-2-yl]thiobenzamide
  参考文献：
  名称：

  Bis(4-hydroxythiazoles): Novel Functional and Switchable Fluorophores

  摘要：

  根据汉茨合成法合成了一系列 2,2′- 和 5,5′- 双（4-羟基噻唑）。这两种酚类化合物及其相应的阴离子在可见光谱中都显示出强烈的荧光，而在去质子化时，其发射会发生浴色转移。这种易于转换的特性使它们能够广泛应用于分析和超分子化学等领域。由于 2,2′-双噻唑具有 1,4-二氮二烯亚基结构，因此具备了与金属络合的先决条件，但分离出的不是铜络合物，而是构成 5,5′-C-C 偶联产物的二聚体。此外，还可以构建三（噻唑）络合物。

  DOI：

  10.1055/s-0030-1260670
• 作为产物：
  描述：

  3-氰基苯甲酰胺 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3-cyanothiobenzamide
  参考文献：
  名称：

  Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets

  摘要：

  Chemoprevention is an approach to decrease cancer morbidity and mortality through inhibition of carcinogenesis and prevention of disease progression. Although the trans stilbene derivative resveratrol has chemopreventive properties, its action is compromised by weak non-specific effects on many biological targets. Replacement of the stilbene ethylenic bridge of resveratrol with a 1,2,4-thiadiazole heterocycle and modification of the substituents on the two aromatic rings afforded potential chemopreventive agents with enhanced potencies and selectivities when evaluated as inhibitors of aromatase and NF-kappa B and inducers of quinone reductase 1 (QR1). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.031

文献信息

• Photochemistry of the Nitrogen-Thiocarbonyl Systems. 30. Intermolecular Photoaddition Reaction of Arenecarbothioamides to 2-Methoxy- and 2-Trimethylsiloxyfurans. Facile Synthesis of Arene-Fused Aminobenzoates by Novel Photoinduced Benzannulation.
  作者：Kazuaki ODA、Masayuki SAKAI、Minoru MACHIDA

  DOI：10.1248/cpb.45.584

  日期：——

  Irradiation of arenecarbothioamides with 2-methoxyfuran in benzene solution gave arene-fused aminobenzoates in moderate yields accompanied by small smounts of arylpyrroles or arylthiophenes. In the case of 2-trimethylsiloxyfuran, arenecarbothioamides gave arene-fused aminobenzoates in good yields as sole products. It was demonstrated that certain furan derivatives are potentially useful as building blocks in photoinduced benzannulation.

  对苯炔羰亚胺在苯溶液中与2-甲氧基呋喃辐照反应，得到中等产率的芳香族融合氨基苯甲酸酯，同时伴随少量的芳香族吡咯或芳香族噻吩。在2-三甲基硅氧呋喃的情况下，苯炔羰亚胺作为唯一产物得到高产率的芳香族融合氨基苯甲酸酯。研究表明，某些呋喃衍生物在光诱导的苯环缩合反应中可能作为有用的构建块。
• Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets
  作者：Abdelrahman S. Mayhoub、Laura Marler、Tamara P. Kondratyuk、Eun-Jung Park、John M. Pezzuto、Mark Cushman

  DOI：10.1016/j.bmc.2011.09.031

  日期：2012.1

  Chemoprevention is an approach to decrease cancer morbidity and mortality through inhibition of carcinogenesis and prevention of disease progression. Although the trans stilbene derivative resveratrol has chemopreventive properties, its action is compromised by weak non-specific effects on many biological targets. Replacement of the stilbene ethylenic bridge of resveratrol with a 1,2,4-thiadiazole heterocycle and modification of the substituents on the two aromatic rings afforded potential chemopreventive agents with enhanced potencies and selectivities when evaluated as inhibitors of aromatase and NF-kappa B and inducers of quinone reductase 1 (QR1). (C) 2011 Elsevier Ltd. All rights reserved.
• Bis(4-hydroxythiazoles): Novel Functional and Switchable Fluorophores
  作者：Dieter Weiß、Rainer Beckert、Eric Täuscher、Lorena Calderón-Ortiz、Helmar Görls

  DOI：10.1055/s-0030-1260670

  日期：2011.7

  A series of 2,2′- and 5,5′-bis(4-hydroxythiazoles) was synthesized according to Hantzsch synthesis. Both phenols and their corresponding anions display a strong fluorescence in the visible spectrum, whereas the emission is shifted bathochromically upon deprotonation. This easy switch makes them suitable for widespread applications, mainly in analysis and supramolecular chemistry. Due to their 1,4-diazadiene substructure, the 2,2′-bithiazoles possess prerequisites for the complexation of metals, however, instead of a copper complex, a dimer which constitutes the 5,5′-C-C coupled product was isolated. In addition, tris(thiazoles) could be constructed.

  根据汉茨合成法合成了一系列 2,2′- 和 5,5′- 双（4-羟基噻唑）。这两种酚类化合物及其相应的阴离子在可见光谱中都显示出强烈的荧光，而在去质子化时，其发射会发生浴色转移。这种易于转换的特性使它们能够广泛应用于分析和超分子化学等领域。由于 2,2′-双噻唑具有 1,4-二氮二烯亚基结构，因此具备了与金属络合的先决条件，但分离出的不是铜络合物，而是构成 5,5′-C-C 偶联产物的二聚体。此外，还可以构建三（噻唑）络合物。