N-[(2-hydroxynaphthalen-1-yl)(phenyl)methyl]thioacetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(2-hydroxynaphthalen-1-yl)(phenyl)methyl]thioacetamide
• 英文别名: N-((2-hydroxynaphthalen-1-yl)(phenyl)methyl)ethanethioamide；N-[(2-hydroxynaphthalen-1-yl)-phenylmethyl]ethanethioamide
• 化学式: C₁₉H₁₇NOS
• 分子量: 307.416
• InChiKey: BCHZXDRZAXPOJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醇 在 choline bisulfate 、 2-hydroxy-N,N,N-trimethyl ethanaminium peroxydisulfate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.67h， 生成 N-[(2-hydroxynaphthalen-1-yl)(phenyl)methyl]thioacetamide
  参考文献：
  名称：

  Choline peroxydisulfate oxidizing Bio-TSIL: triple role player in the one-pot synthesis of Betti bases and gem-bisamides from aryl alcohols under solvent-free conditions

  摘要：

  一锅法合成Betti碱和双酰胺，使用可生物降解的胆碱过硫酸盐。

  DOI：

  10.1039/c4nj02295e

文献信息

• Triethylamine-bonded sulfonic acid ([Et₃N–SO₃H]Cl): a highly efficient and homogeneous catalyst for the condensation of 2-naphthol with arylaldehydes and amides (alkyl carbamates or thioamides)
  作者：Abdolkarim Zare、Shayesteh Akbarzadeh、Elmira Foroozani、Hamideh Kaveh、Ahmad Reza Moosavi-Zare、Alireza Hasaninejad、Mohammad Mokhlesi、Mohammad Hassan Beyzavi、Mohammad Ali Zolfigol

  DOI：10.1080/17415993.2012.690415

  日期：2012.6

  Ionic liquid triethylamine-bonded sulfonic acid ([Et 3N–SO 3H]Cl, N,N-diethyl-N-sulfoethanammonium chloride) is utilized as a highly efficient, inexpensive and homogeneous catalyst to promote the following one-pot multi-component organic transformations under solvent-free conditions: (i) the condensation of 2-naphthol with arylaldehydes and amides leading to 1-amidoalkyl-2-naphthols, (ii) the reaction

  离子液体三乙胺键合磺酸（[Et 3N-SO 3H]Cl，N,N-二乙基-N-磺基氯化铵）被用作一种高效、廉价且均相的催化剂，以促进以下一锅多组分有机无溶剂条件下的转化：(i) 2-萘酚与芳醛和酰胺缩合生成 1-酰胺基烷基-2-萘酚，(ii) 2-萘酚与芳香醛和氨基甲酸烷基酯反应生成 1-氨基甲酸烷基-2-萘酚，以及 (iii) 2-萘酚、芳醛和硫代酰胺之间的缩合反应，生成 1-硫代酰胺基烷基-2-萘酚。高产率、短反应时间、效率、通用性、清洁过程、方法简单、成本低、易于处理、易于制备催化剂以及环境友好的条件是该协议的一些优点。
• A highly effective and mild protocol for the production of 1-thioamidoalkyl-2-naphthols using 1,3-disulfonic acid imidazolium trifluoroacetate as a dual-functional catalyst
  作者：Mostafa Karami、Abdolkarim Zare

  DOI：10.1515/znb-2018-0001

  日期：2018.5.24

  A solvent-free protocol for the production of 1-thioamidoalkyl-2-naphthols via a one-pot multi-component reaction of arylaldehydes with 2-naphthol and thioacetamide using the ionic liquid 1,3-disulfonic acid imidazolium trifluoroacetate ([Dsim][TFA]) is described. Furthermore, a plausible and attractive mechanism based on the dual functionality of the catalyst is proposed. Because of the dual functionality of [Dsim][TFA] (possessing acidic and basic sites), it is found to be generally highly effective, affording the products in high yields and short reaction times under mild conditions. We claim that this is one of the best protocols for the synthesis of 1-thioamidoalkyl-2-naphthols (in terms of yield, temperature, conditions, and/or the reaction time).

  一个无溶剂的方法，通过芳香醛与2-萘酚和硫代乙酰胺的一锅多组分反应，在离子液体1,3-二磺酸咪唑三氟乙酸盐([Dsim][TFA])的催化下合成1-硫代氨基烷基-2-萘酚。此外，提出了一个基于催化剂双重功能性的合理且有吸引力的机理。由于[Dsim][TFA]具有酸性和碱性位点的双重功能性，它被发现通常非常有效，在温和条件下以高产率和短反应时间提供产物。我们声称这是合成1-硫代氨基烷基-2-萘酚的最佳方法之一(就产率、温度、条件和/或反应时间而言)。
• Highly effective synthesis of 1-thioamidoalkyl-2-naphthols and tetrahydropyridines using a nanostructured silica-based catalyst under mild conditions
  作者：Navid Irannejad-Gheshlaghchaei、Seyed Sajad Sajadikhah

  DOI：10.2174/1386207323666200914092345

  日期：2020.9.14

  Mass spectroscopy. Results: One-pot multi-component condensation of 2-naphthol with arylaldehydes and thioacetamide catalyzed by nano-[DSPECDA][HSO4] under green, mild and solvent-free conditions led to 1-thioamidoalkyl-2-naphthols in high yields. The nanocatalyst was also used for the preparation of functionalized tetrahydropyridines by the one-pot multi-component reaction of anilines, arylaldehydes

  目的和目的：Nano-2-[N',N'-dimethyl-N'-(silica-n-丙基)ethanaminium chloride]-N,N-dimethylaminium bisulfate (nano-[DSPECDA][HSO4])用作一种高效的非均相二氧化硅基纳米结构催化剂，用于合成 1-硫代氨基烷基-2-萘酚和取代的四氢吡啶。 材料与方法：预期产品在温和条件下制备。在这项工作中，合成了三种新型 1-硫代酰胺烷基-2-萘酚和两种新型四氢吡啶衍生物，并通过 IR、1 H 和13 C NMR 和质谱进行了表征。 结果：纳米-[DSPECDA][HSO 4 ] 催化2-萘酚与芳醛和硫代乙酰胺在绿色、温和、无溶剂条件下的一锅多组分缩合反应得到高收率的1-硫代氨基烷基-2-萘酚。该纳米催化剂还用于在无溶剂和温和条件下通过苯胺、芳基醛和乙酰乙酸乙酯的一锅多组分反应制备官能化四氢吡啶。 结论：
• 1,3-Dibromo-5,5-dimethylhydantoin as an efficient catalyst for synthesis of thioamidoalkyl and bis(thio)amidoalkyl-2-naphthols under solvent-free conditions
  作者：Arash Ghorbani-Choghamarani、Shima Rashidimoghadam

  DOI：10.1007/s11164-014-1738-y

  日期：2015.9

  An efficient and easy method for one-pot three-component synthesis of thioamidoalkyl and bis(thio)amidoalkyl naphthols by condensation of aromatic aldehydes, 2-naphthol, and acetamide or thioacetamide under thermal condition at 130 °C in the presence of 1,3-dibromo-5,5-dimethylhydantoin is described. The present approach offers several advantages such as reduced reaction time, higher yield, and economic availability of the catalyst.

  一种高效且简便的一锅法三组分合成硫代氨基烷基和双(硫代)氨基烷基萘酚的方法，通过芳香醛、2-萘酚和乙酰胺或硫乙酰胺在130°C，存在1,3-二溴-5,5-二甲基海因的条件下进行缩合反应。该方法具有反应时间短、产率高和催化剂经济易得等优点。
• A Three-Component Novel Synthesis of 1-[Aryl(Thioacetamido)Methyl]-2-Naphthol Derivatives
  作者：Alireza Hassanabadi、Mohammad R. Hosseini-Tabatabaei

  DOI：10.3184/174751912x13408123396599

  日期：2012.9

  between 2-naphthol, an aryl aldehydes and thioacetamide catalysed by p-toluenesulfonic acid under reflux conditions provided a simple and efficient one-pot route for the synthesis of 1-[aryl(thioacetamido)methyl]-2-naphthol derivatives in excellent yields.

  在回流条件下，对甲苯磺酸催化的 2-萘酚、芳基醛和硫代乙酰胺的三组分反应为合成 1-[芳基（硫代乙酰胺）甲基]-2-萘酚提供了一种简单有效的一锅法以优异的收率衍生。