2-methyl-6-(phenylthio)-N-(quinolin-8-yl)benzamide | 1404616-67-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methyl-6-(phenylthio)-N-(quinolin-8-yl)benzamide
• 英文别名: 2-Methyl-6-phenylthio-N-(quinolin-8-yl)benzamide；2-methyl-6-phenylsulfanyl-N-quinolin-8-ylbenzamide
• CAS: 1404616-67-6
• 化学式: C₂₃H₁₈N₂OS
• 分子量: 370.475
• InChiKey: HMSOWCRGLRLIKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻甲基苯甲酰氯 在 [nickel(II)dichloride(dimethoxyethane)] 、 叔丁基锂 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 生成 2-methyl-6-(phenylthio)-N-(quinolin-8-yl)benzamide
  参考文献：
  名称：

  Nickel-catalyzed directed sulfenylation of sp² and sp³ C–H bonds

  摘要：

  通过镍催化的定向C-S键形成，实现了对sp2和sp3碳氢键的硫烯化，产率良好至优异（高达90%）。

  DOI：

  10.1039/c5cc01970b

文献信息

• Nickel-catalyzed synthesis of diarylsulfides and sulfones via C–H bond functionalization of arylamides
  作者：Vutukuri Prakash Reddy、Renhua Qiu、Takanori Iwasaki、Nobuaki Kambe

  DOI：10.1039/c5ob00149h

  日期：——

  The sulfenylation and sulfonylation of (sp²)C–H bonds of benzamides were achieved with the aid of a bidentate directing group.

  苯甲酰胺的(sp²)C-H键的磺化和磺酰化在双齿导向基的辅助下实现。
• Nickel-catalyzed thiolation of unactivated aryl C–H bonds: efficient access to diverse aryl sulfides
  作者：Sheng-Yi Yan、Yue-Jin Liu、Bin Liu、Yan-Hua Liu、Bing-Feng Shi

  DOI：10.1039/c4cc10446c

  日期：——

  A nickel-catalyzed thiolation of unactivated C(sp²)–H bonds with disulfides employing the PIP directing group was described. This process uses a catalytic nickel catalyst and no metallic oxidants or cocatalysts are required. Moreover, the reaction tolerates various important functional groups and heteroarenes.

  一种使用PIP导向基团催化的镍催化硫化未活化的C(sp2)-H键与二硫化物的方法被描述。该过程使用催化镍催化剂，无需金属氧化剂或共催化剂。此外，该反应能容忍各种重要的官能团和杂环化合物。
• Cobalt-Catalyzed Direct C–H Thiolation of Aromatic Amides with Disulfides: Application to the Synthesis of Quetiapine
  作者：Mingliang Li、Jun “Joelle” Wang

  DOI：10.1021/acs.orglett.8b02812

  日期：2018.10.19

  A direct C(sp2)–H thiolation of aromatic amides with disulfides was developed. The coupling reaction proceeds between the thioether radical and cobaltacycle intermediate. This method exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that the cobalt(IV) intermediate is probably formed during the course of the reaction. The thiolation product

  已开发出具有二硫化物的芳族酰胺的直接C（sp 2）-H硫醇化反应。偶联反应在硫醚基和钴环中间体之间进行。该方法表现出相对较宽的底物范围和高官能团相容性。机理研究表明，钴（IV）中间体可能在反应过程中形成。硫醇化产物可以转化为喹硫平，喹硫平是一种批准用于治疗精神分裂症和躁郁症的非典型抗精神病药。
• Palladium-Catalyzed Direct Thiolation of Aryl CH Bonds with Disulfides
  作者：Masayuki Iwasaki、Miki Iyanaga、Yuta Tsuchiya、Yugo Nishimura、Wenjuan Li、Zhiping Li、Yasushi Nishihara

  DOI：10.1002/chem.201304717

  日期：2014.2.24

  A catalytic variant of the direct thiolation of arenes, bearing directing groups, with disulfides or thiols has been developed under palladium and copper co‐catalysis. Both sulfenyl moieties of the disulfide could be incorporated into the thiolated products, therefore, the reactions reached completion with only half an equivalent of disulfide, with respect to the starting arene. Experimental evidence

  在钯和铜的共催化下，开发了带有二价硫或硫醇的带有导向基团的芳烃直接硫醇化的催化变体。二硫化物的两个亚硫基部分都可以结合到硫醇化产物中，因此，相对于起始芳烃，仅用一半当量的二硫化物就可以完成反应。实验证据表明该反应是通过Pd II / Pd IV机制进行的。
• Direct<i>ortho</i>-Thiolation of Arenes and Alkenes by Nickel Catalysis
  作者：Cong Lin、Danyang Li、Binjie Wang、Jinzhong Yao、Yuhong Zhang

  DOI：10.1021/acs.orglett.5b00337

  日期：2015.3.6

  The direct thiolation of arenes and alkenes with diaryl disulfides was developed by nickel catalysis. The reaction displayed exceptional compatibility with a wide range of functional groups to regioselectively give the diaryl sulfides and alkenyl sulfides in high yields.