N-(n-Butyl)-2-mercaptonicotinamid | 65282-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(n-Butyl)-2-mercaptonicotinamid
• 英文别名: N-butyl-2-sulfanylpyridine-3-carboxamide
• CAS: 65282-55-5
• 化学式: C₁₀H₁₄N₂OS
• mdl: MFCD24389589
• 分子量: 210.3
• InChiKey: MJSKXMNEKRNPAO-UHFFFAOYSA-N

物化性质

• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(n-Butyl)-2-mercaptonicotinamid 在 劳森试剂 、 硫化氢 、 mercury(II) diacetate 、 碘 、 碳酸氢钠 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 3.5h， 生成 1,2-dithiolo<5,4-b>pyridin-3-one
  参考文献：
  名称：

  3H-[1,2]Dithiolo[3,4-b]pyridine-3-thione and its derivatives Synthesis and antimicrobial activity

  摘要：

  A series of 2-substituted isothiazolo[5,4-b]pyridine-3(2H)-thiones isothiazolo[5,4-b]pyridin-3(2H)-ones, N-substituted 2-sulfanylnicotinamides and the corresponding carbothioamide derivatives were synthesized and evaluated for their antimicrobial activity against several strains of Gram + and Gram - bacteria and fungi. Chemical syntheses were resumed into a comprehensive cyclic route that enables the reversible conversion for each derivative of the series considered. Among the tested compounds the N-(aralkyl)-2-sulfanylnicotinamides show the highest fungitoxicity (MIC = 1.25-5 mug/ml). The best activity towards Gram-positive bacteria was in the range of 2.5-5 mug/ml. Activity against Gram-negative bacteria was generally very poor for all compounds. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00084-7
• 作为产物：
  描述：

  2-propylisothiazolo<5,4-b>pyridine-3(2H)-thione 在 劳森试剂 、 tetraphosphorus decasulfide 、 硫化氢 、 mercury(II) diacetate 、 碘 、 碳酸氢钠 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 甲苯 、 xylene 为溶剂， 反应 8.0h， 生成 N-(n-Butyl)-2-mercaptonicotinamid
  参考文献：
  名称：

  3H-[1,2]Dithiolo[3,4-b]pyridine-3-thione and its derivatives Synthesis and antimicrobial activity

  摘要：

  A series of 2-substituted isothiazolo[5,4-b]pyridine-3(2H)-thiones isothiazolo[5,4-b]pyridin-3(2H)-ones, N-substituted 2-sulfanylnicotinamides and the corresponding carbothioamide derivatives were synthesized and evaluated for their antimicrobial activity against several strains of Gram + and Gram - bacteria and fungi. Chemical syntheses were resumed into a comprehensive cyclic route that enables the reversible conversion for each derivative of the series considered. Among the tested compounds the N-(aralkyl)-2-sulfanylnicotinamides show the highest fungitoxicity (MIC = 1.25-5 mug/ml). The best activity towards Gram-positive bacteria was in the range of 2.5-5 mug/ml. Activity against Gram-negative bacteria was generally very poor for all compounds. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00084-7

文献信息

• A transition metal-free tandem process to pyridazinopyrido[3,2-f][1,4]thiazepine-diones via Smiles rearrangement
  作者：Xiaoyi Niu、Bingchuan Yang、Yanqiu Li、Shuai Fang、Zixiao Huang、Caixia Xie、Chen Ma

  DOI：10.1039/c3ob40719e

  日期：——

  A transition metal-free methodology for the synthesis of pyridazinopyrido[3,2-f][1,4]thiazepine-diones was studied. The construction of this tricyclic system went through a one-pot coupling/Smiles rearrangement/cyclization process. The high yields of pure products were obtained through simple recrystallization.

  研究了一种合成哒嗪并吡啶并[3,2-f][1,4]硫氮杂卓二酮的无过渡金属方法。该三环体系的构建是通过一锅耦合/斯迈尔斯重排/环化过程完成的。通过简单的重结晶获得了高产率的纯产品。
• Process for depigmenting keratin materials using thiopyridinone compounds
  申请人：L'OREAL

  公开号：US11052028B2

  公开（公告）日：2021-07-06

  The invention relates to cosmetic processes and compositions for depigmenting, lightening and/or whitening keratin materials, in particular the skin, which comprises the application of a cosmetic composition comprising thiopyridinone compounds to keratin materials.

  本发明涉及用于脱色、淡化和/或美白角质材料（尤其是皮肤）的化妆品工艺和组合物，其中包括将包含噻啶酮化合物的化妆品组合物用于角质材料。
• Transition Metal-Free One-Pot Synthesis of Fused 1,4-Thiazepin-5(4<i>H</i>)-ones and Theoretical Study of the S–N Type Smiles Rearrangement Process
  作者：Bingchuan Yang、Xiaochen Tan、Ruiying Guo、Shunwei Chen、Zeyuan Zhang、Xianglong Chu、Caixia Xie、Dongju Zhang、Chen Ma

  DOI：10.1021/jo5011729

  日期：2014.9.5

  A series of 1,4-thiazepin-5(4H)-one derivatives were synthesized via a transition metal-free one-pot Smiles rearrangement process at room temperature. Regioselective seven-membered heterocycles were constructed in good to excellent yields. To gain an in-depth understanding of the S-N type Smiles rearrangement mechanism, a theoretical study was also performed by quantum chemistry calculations.
• PROCESS FOR DEPIGMENTING KERATIN MATERIALS USING THIOPYRIDINONE COMPOUNDS
  申请人：L'Oréal

  公开号：EP2651897A1

  公开（公告）日：2013-10-23
• US9138392B2
  申请人：——

  公开号：US9138392B2

  公开（公告）日：2015-09-22