N-benzylpentanethioamide | 163313-56-2

• 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: N-benzylpentanethioamide
• 英文别名: Pentanethioamide, N-(phenylmethyl)-
• CAS: 163313-56-2
• 化学式: C₁₂H₁₇NS
• 分子量: 207.34
• InChiKey: ZLBCTVCIVXCKFR-UHFFFAOYSA-N

物化性质

• 沸点：
  310.5±35.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-乙酰基噻吩 、 N-benzylpentanethioamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以51%的产率得到5-methyl-4-phenyl-5-(2-thienyl)-1,3-oxazolidine-2-thione
  参考文献：
  名称：

  C-Aminoimidoylation and C-Thiocarbamoylation of Esters, Sulfones, and Ketones

  摘要：

  Esters, sulfones, and ketones were C-aminoimidoylated and C-thiocarbamoylated by benzotriazole-1-carboxamidines 8a-g and 1-(alkyl-or-arylthiocarbamoyl)benzotriazoles 9a-i, respectively. The present work represents the first systematic approach to these compound classes, the few previously known examples of which were obtained by diverse approaches.

  DOI：

  10.1021/jo070545c
• 作为产物：
  描述：

  正丁基锂 、 异硫氰酸苯甲酯 以88%的产率得到N-benzylpentanethioamide
  参考文献：
  名称：

  通过在环戊基甲基醚（CPME）中将有机锂试剂添加到异硫氰酸酯中，获得二级硫代酰胺的可靠，环保的方法

  摘要：

  在异硫氰酸酯中亲和性广泛获得的各种官能化有机锂试剂的亲核加成反应是直接，高产率，一锅法获得仲硫代酰胺的方法。所需的简单反应条件和广泛的应用范围（> 50个案例）使其成为一种既简便又复杂的硫酰胺类（包括对映纯类）的可靠可靠的检测方法。在整个合成过程中避免使用通常在文献确定的方法中使用的有毒和难闻的硫化剂，从而使该方案在可持续性方面也具有很高的吸引力。

  DOI：

  10.1002/chem.201504247

文献信息

• A New Versatile One-Pot Synthesis of Functionalized Thioamides From Grignards, Carbon Disulfide and Amines
  作者：Alan R. Katritzky、Jean-Luc Moutou、Zhijun Yang

  DOI：10.1055/s-1995-4144

  日期：1995.12

  The one-pot successive reactions of Grignard reagents with carbon disulfide and amines mediated by 1-trifluoromethylsulfonylbenzotriazole or triflic anhydride, provide and attractive and general route to thioamides. A wide variety of amines (primary alkyl, arylalkyl, secondary alkyl, cyclic amines, aniline, N-substituted anilines, heterocyclic amidines, amino alcohols, amino ethers, amino acetals, amino ketones, amino esters, amino amides (peptides), aminoalkenes, and diamines) and Grignard (primary alkyl, arylalkyl, aryl, secondary alkyl and tertiary alkyl) can be used, and thioamides are generally formed in good to moderate yields.

  由1-三氟甲磺酰苯并三唑或三氟甲磺酸酐介导的Grignard试剂与二硫化碳和胺的一锅连续反应提供了一条吸引人的、通用的硫酰胺合成途径。广泛种类的胺（一级烷基、芳基烷基、二级烷基、环状胺、苯胺、N-取代苯胺、杂环脒、氨基醇、氨基醚、氨基缩醛、氨基酮、氨基酯、氨基酰胺（肽）、氨基烯烃和二胺）以及Grignard试剂（一级烷基、芳基烷基、芳基、二级烷基和三级烷基）均可使用，并且通常以良好至中等的产率形成硫酰胺。
• Preparation of thioamides from alkyl bromides, nitriles, and hydrogen sulfide through a thio-Ritter-type reaction
  作者：Shi-Zhong Tang、Kai Xiang、Rui Ye、Meng-En Chen、Jian-Chang Yu、Zhi-Juan He、Fu-Min Zhang

  DOI：10.1039/d2cc04210j

  日期：——

  A novel thio-Ritter-type reaction of alkyl bromides, nitriles, and hydrogen sulfide has been explored, providing a straightforward approach toward functionally important thioamides. This transformation features a broad substrate scope, operational simplicity, use of available feedstock chemicals, and late-stage functionalizations of bioactive molecules. The reaction mechanism is also proposed.

  已经探索了烷基溴、腈和硫化氢的新型硫代里特型反应，为功能重要的硫代酰胺提供了一种直接的方法。这种转化具有广泛的底物范围、操作简单、使用可用的原料化学品和生物活性分子的后期功能化。还提出了反应机理。
• A Robust, Eco‐Friendly Access to Secondary Thioamides through the Addition of Organolithium Reagents to Isothiocyanates in Cyclopentyl Methyl Ether (CPME)
  作者：Vittorio Pace、Laura Castoldi、Serena Monticelli、Sandra Safranek、Alexander Roller、Thierry Langer、Wolfgang Holzer

  DOI：10.1002/chem.201504247

  日期：2015.12.21

  The nucleophilic addition of widely available and variously functionalized organolithium reagents to isothiocyanates represents a straightforward, high‐yielding, one‐pot method to access secondary thioamides. The simple reaction conditions required and the broad scope (>50 cases examples) makes it a robust and reliable method to access both simple and complex thioamides, including enantiopure ones

  在异硫氰酸酯中亲和性广泛获得的各种官能化有机锂试剂的亲核加成反应是直接，高产率，一锅法获得仲硫代酰胺的方法。所需的简单反应条件和广泛的应用范围（> 50个案例）使其成为一种既简便又复杂的硫酰胺类（包括对映纯类）的可靠可靠的检测方法。在整个合成过程中避免使用通常在文献确定的方法中使用的有毒和难闻的硫化剂，从而使该方案在可持续性方面也具有很高的吸引力。
• C-Aminoimidoylation and C-Thiocarbamoylation of Esters, Sulfones, and Ketones
  作者：Alan R. Katritzky、Niveen M. Khashab、Danniebelle N. Haase、Megumi Yoshioka、Ion Ghiviriga、Peter J. Steel

  DOI：10.1021/jo070545c

  日期：2007.8.31

  Esters, sulfones, and ketones were C-aminoimidoylated and C-thiocarbamoylated by benzotriazole-1-carboxamidines 8a-g and 1-(alkyl-or-arylthiocarbamoyl)benzotriazoles 9a-i, respectively. The present work represents the first systematic approach to these compound classes, the few previously known examples of which were obtained by diverse approaches.