N,N-dimethyloctanethioamide | 125188-66-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代酰胺
• 英文名称: N,N-dimethyloctanethioamide
• CAS: 125188-66-1
• 化学式: C₁₀H₂₁NS
• 分子量: 187.349
• InChiKey: MZFPIMMGDQECDR-UHFFFAOYSA-N

物化性质

• 沸点：
  240.3±23.0 °C(Predicted)
• 密度：
  0.910±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  乙酸烯丙酯 、 N,N-dimethyloctanethioamide 在 bis(η3-allyl-μ-chloropalladium(II)) 、 1,4-双(二苯基膦)丁烷 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以79%的产率得到N,N-dimethyl-2-prop-2-enyloctanethioamide
  参考文献：
  名称：

  Pd-catalyzed allylic alkylation of thioamides

  摘要：

  This work describes the first Pd-catalyzed allylic alkylation of thioamides. Various thioamides were efficiently alpha-allylated in high yields and with excellent selectivity for monoallylation under mild reaction conditions. The process not only provides a facile method for the synthesis of functionalized thioamides, but also presents a useful transformation for synthetically important thioamides. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.081
• 作为产物：
  描述：

  甲酸辛酯 、 N,N-二甲基甲酰胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 乙二胺四乙酸 、 sodium hydroxide 作用下， 以65 %的产率得到N,N-dimethyloctanethioamide
  参考文献：
  名称：

  温和条件下硫代酰胺的一般构建：由 EDTA 介导的逐步质子转移过程

  摘要：

  结合实验和量子化学计算，研究了一种通用、清洁和有效的硫代酰胺一锅合成方案。酯、酰胺和元素硫用作起始原料，乙二胺四乙酸 (EDTA) 作为催化剂以促进良性反应。EDTA 的催化作用归因于逐步质子转移过程，其中 EDTA 将质子从苄基碳转移到硫原子。

  DOI：

  10.1002/ejoc.202101013

文献信息

• Transition-Metal-Free Cleavage of C–C Triple Bonds in Aromatic Alkynes with S₈ and Amides Leading to Aryl Thioamides
  作者：Kai Xu、Ziyi Li、Fangyuan Cheng、Zhenzhen Zuo、Tao Wang、Mincan Wang、Lantao Liu

  DOI：10.1021/acs.orglett.8b00573

  日期：2018.4.20

  transition-metal-free cleavage reaction of C–C triple bonds in aromatic alkynes with S8 and amides furnishes aryl thioamides in moderate to excellent yields. The remarkable features of this thioamidation include the metal-free cleavage of C–C triple bond, mild reaction conditions, as well as wide substrate scope that is particularly compatible with some internal aromatic alkynes and acetamides.

  芳香族炔烃中的C–C三键与S 8和酰胺的新型无过渡金属裂解反应以中等至极好的收率提供了芳基硫代酰胺。硫代酰胺化反应的显着特征包括C-C三键的无金属裂解，温和的反应条件以及宽泛的底物范围，特别是与某些内部芳族炔烃和乙酰胺兼容。
• Transition‐Metal‐Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur
  作者：Hao Jin、Xinzhi Chen、Chao Qian、Xin Ge、Shaodong Zhou

  DOI：10.1002/ejoc.202100588

  日期：2021.6.21

  A general method for one-pot synthesis of thioamides without transition metals or external oxidants is developed through a three-component reaction involving chlorohydrocarbon, amide and elemental sulfur. Both alkyl and aryl thioamides could be obtained in moderate to excellent yields through this protocol. A high tolerance regarding various substituents on chlorohydrocarbon or amide was justified

  通过涉及氯代烃、酰胺和元素硫的三组分反应开发了一种无需过渡金属或外部氧化剂的一锅法合成硫代酰胺的通用方法。通过该协议，可以以中等至极好的收率获得烷基和芳基硫代酰胺。对氯代烃或酰胺上的各种取代基的高耐受性是合理的。值得注意的是，该协议不需要过渡金属或外部氧化剂。此外，还结合控制实验和量子化学计算对反应机制进行了研究。
• Pd-catalyzed asymmetric α-allylic alkylation of thioamides
  作者：Bin Rong、Qin Yang、Yong Liu、Hong Xu、Yifan Hu、Xuejing Cheng、Baoguo Zhao

  DOI：10.1016/j.tetlet.2014.12.031

  日期：2015.1

  This Letter describes the first catalytic asymmetric alpha-allylic alkylation of thioamides. By using 5 mol % Pd-(R)-DM-BINAP complex as the chiral catalyst, various thioamides were efficiently alpha-allylic alkylated with 1,3-diarylallyl carbonates under mild conditions, affording a variety of alpha-substituted thioamides in good yields with high enantioselectivity and moderate diastereoselectivity. This work represents a useful and direct route to prepare chiral functionalized thioamides. (C) 2014 Elsevier Ltd. All rights reserved.
• Pd-catalyzed α-arylation of thioamides
  作者：Hailei Yu、Xuliang Liu、Lei Ding、Qin Yang、Bin Rong、Ang Gao、Baoguo Zhao、Haifeng Yang

  DOI：10.1016/j.tetlet.2013.03.114

  日期：2013.6

  Thioamides are unique and versatile synthetic building blocks with S, N, and alpha-C three adjacent nucleophile centers, however, they are rarely used as carbon nucleophiles for transition-metal-catalyzed C-C coupling reactions. This Letter describes the first Pd-catalyzed alpha-arylation of thioamides and demonstrated the feasibility of the application of thioamides in coupling chemistry. By the coupling process, a variety of alpha-arylated thioamides were prepared in moderate to good yields under mild reaction conditions, which provides an alternative way to access functionalized thioamides as well as a new synthetic transformation for thioamides. High chemoselectivity for thioamide over amide was observed in the reaction. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel reaction for the preparation of alkyl vinyl sulfides using metal complex catalysts
  作者：U. M. Dzhemilev、N. Z. Baibulatova、R. V. Kunakova、T. K. Tkachenko、G. A. Tolstikov

  DOI：10.1007/bf00958250

  日期：1990.9

  The feasibility of the one-step synthesis of mixtures of Z- and E-alkenyl alkyl sulfides via the reaction of elemental sulfur with terminal and disubstituted alkynes and alkyl halides has been demonstrated in the presence of low-valent Ni, Co, Pd, and Fe complexes. The effects of structure in the starting alkynes and alkyl halides have been investigated, along with process conditions and their effect on the composition and yields of reaction products.