(3,4-dihydroisoquinoline-2(1H)-yl)(phenyl)methanethione | 122709-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (3,4-dihydroisoquinoline-2(1H)-yl)(phenyl)methanethione
• 英文别名: (3,4-dihydroisoquinolin-2(1H)-yl)(phenyl)methanethione；3,4-dihydro-1H-isoquinolin-2-yl(phenyl)methanethione
• CAS: 122709-96-0
• 化学式: C₁₆H₁₅NS
• 分子量: 253.368
• InChiKey: CBRIVDYNKHUVDI-UHFFFAOYSA-N

物化性质

• 沸点：
  395.4±52.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯甲酸 在 sodium hydrogen sulfide 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 间二甲苯 为溶剂， 反应 2.0h， 生成 (3,4-dihydroisoquinoline-2(1H)-yl)(phenyl)methanethione
  参考文献：
  名称：

  Ynamide 介导的硫代酰胺和伯硫代酰胺合成

  摘要：

  描述了用于合成硫代酰胺和伯硫代酰胺的环保型 ynamide 介导的单硫代羧酸与胺或氢氧化铵的硫代酰胺化反应。简单温和的反应条件使反应能够耐受多种官能团，例如羟基、酯、叔胺、酮和酰胺部分。现成的 NaSH 作为硫源，避免使用有毒、昂贵和恶臭的有机硫试剂，使该策略对环境友好且实用。重要的是，α-手性单硫代羧酸的立体化学完整性在活化步骤和随后的氨解过程中得以保持，从而为肽 C 末端修饰提供了一种无外消旋化策略。此外，

  DOI：

  10.1021/acs.joc.1c03076

文献信息

• X=Y-ZH systems as potential 1,3-dipoles
  作者：Moustafa F. Aly、Ronald Grigg

  DOI：10.1016/s0040-4020(01)86099-3

  日期：1988.1

  α-Imino acids, prepared from α-keto acids and primary amines, undergo facile decarboxylation to the corresponding imines on heating at ⩽,80°C in benzene or methylene chloride. Decarboxylation proceeds via a 1,2-ylide which can be trapped by sulphur to give the corresponding secondary thioamides in good yield. 1,2-Ylides from secondary amines and ∞-keto acids can be generated in situ and trapped with

  由α-酮酸和伯胺制得的α-氨基酸在⩽80℃下于苯或二氯甲烷中加热时，容易脱羧成相应的亚胺。脱羧反应通过1,2-ylide进行，可以被硫捕获，从而以高收率得到相应的仲硫代酰胺。来自仲胺和∞-酮酸的1,2-内酯可以原位生成并用硫捕获，从而以优异的收率得到叔硫酰胺。
• Carbon nitride creates thioamides in high yields by the photocatalytic Kindler reaction
  作者：B. Kurpil、B. Kumru、T. Heil、M. Antonietti、A. Savateev

  DOI：10.1039/c7gc03734a

  日期：——

  based photocatalyst, effectively promotes the Kindler reaction of thioamide bond formation using amines and elemental sulfur as building blocks under visible light irradiation. The feasibility of the developed methodology was confirmed using 14 different primary and secondary amines, including substituted benzylamines and heterocyclic and aliphatic methylamines, which were successfully converted into

  聚庚庚二酰亚胺钾（一种基于氮化碳的光催化剂）在可见光照射下，以胺和元素硫为基础，有效地促进了硫酰胺键形成的金德勒反应。使用14种不同的伯胺和仲胺（包括取代的苄胺以及杂环和脂肪族甲胺）已证实了所开发方法的可行性，这些胺已成功转化为硫代酰胺，分离产率为68-92％。
• Sulfur‐Catalyzed Oxidative Coupling of Dibenzyl Disulfides with Amines: Access to Thioamides and Aza Heterocycles
  作者：Thanh Binh Nguyen、Le Phuong Anh Nguyen、Thi Thu Tram Nguyen

  DOI：10.1002/adsc.201801695

  日期：2019.4.16

  In the presence of catalytic amounts of elemental sulfur, dibenzyl disulfide/DMSO was found to be an excellent thiobenzoylating agent of amines to provide a wide range of thioamides. The reaction becomes autocatalytic when anilines substituted by an o‐cyclizable group were used as nucleophile, leading to the corresponding 2‐aryl aza heterocycles.

  发现在催化量的元素硫存在下，二苄基二硫化物/ DMSO是一种出色的胺硫代苯甲酰化剂，可提供多种硫酰胺。当被邻环化基团取代的苯胺用作亲核试剂时，该反应变为自催化反应，从而导致相应的2-芳基氮杂杂环。
• Ready decarboxylation of imines of α-keto acids. Mechanism and application to thioamide synthesis
  作者：Moustafa F. Aly、Ronald Grigg

  DOI：10.1039/c39850001523

  日期：——

  α-Keto a ids are readily decarboxylated via imine formation with primary and/or secondary amines even when imine–enamine isomerisation can occur; the process is thoyghy to involve an intermediate zwitteriion which can be trapped by sulphur to give thiamides in excellent yield.

  即使发生亚胺-烯胺异构化反应，α-酮基ids也很容易通过亚胺与伯胺和/或仲胺的形成而被羧化。该方法非常复杂，涉及一种中间体两性离子，该两性离子可被硫捕获，从而以优异的收率得到硫代酰胺。
• Thiol as a Synthon for Preparing Thiocarbonyl: Aerobic Oxidation of Thiols for the Synthesis of Thioamides
  作者：Xi Wang、Miran Ji、Seungyeon Lim、Hye-Young Jang

  DOI：10.1021/jo501378v

  日期：2014.8.1

  It is a constant challenge to develop an environmentally friendly, atom-economical, and step-economical method for the preparation of thioamides. Herein, we describe an oxidation method that affords the direct conversion of thiols to thioamides without the use of exogenous sulfur reagents. This is the first instance of a successful utilization of thiols as a synthon for the preparation of thioamides under economical conditions.