N,N'-dibenzyl-benzene-1,3-dicarbothioamide | 1047661-71-1

• 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,N'-dibenzyl-benzene-1,3-dicarbothioamide
• 英文别名: 1-N,3-N-dibenzylbenzene-1,3-dicarbothioamide
• CAS: 1047661-71-1
• 化学式: C₂₂H₂₀N₂S₂
• 分子量: 376.546
• InChiKey: JYKPEKLENBEOSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  88.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-dibenzyl-benzene-1,3-dicarbothioamide 在 N(CH₂CH₃)3 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 生成 [2,6-bis(benzylaminothiocarbonyl)-κ2S,S'-phenyl-κC1]chloroplatinum(II)(1-)
  参考文献：
  名称：

  Chemical Stimuli Induced Phosphorescence Modulation of Secondary Thioamide-Based Pincer Platinum Complexes

  摘要：

  The photochemical properties of pincer platinum complexes bearing secondary thioamide groups have been examined. The presence of the coordinated secondary thioamide linkage in the pincer ligand was found to work as a reactive site upon addition of bases and anions and to result in modulating absorption and emission properties of the complexes.

  DOI：

  10.1021/om800894j
• 作为产物：
  描述：

  间苯二甲醛 、 苄胺 在 sulfur 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以79%的产率得到N,N'-dibenzyl-benzene-1,3-dicarbothioamide
  参考文献：
  名称：

  使用分子氧作为氧化剂的铜催化氧化脱硫促进硫代酰胺的分子内环化：获得五至七元含氮杂环的有效途径

  摘要：

  铜催化氧化脱硫促进硫代酰胺的分子内环化反应在中性和温和条件下，以分子氧为氧化剂进行。该过程...

  DOI：

  10.1246/cl.2008.646

文献信息

• Luminescence Study of Thioamide-based Pincer Palladium Complexes in Poly(vinylpyrrolidone) Matrix
  作者：Yasuyuki Ogawa、Ayako Taketoshi、Junpei Kuwabara、Ken Okamoto、Takashi Fukuda、Takaki Kanbara

  DOI：10.1246/cl.2010.385

  日期：2010.4.5

  Pincer palladium complexes bearing secondary thioamide units exhibit strong phosphorescence at room temperature upon incorporation into poly(vinylpyrrolidone) matrix; a hybrid film shows reversible switching of luminescence upon exposure to volatile organic compounds.

  含有二级硫代酰胺单元的钳形钯复合物加入聚乙烯吡咯烷酮基质后，在室温下显示出强烈的磷光；混合薄膜在暴露于挥发性有机化合物时显示出可逆的发光切换。
• Deprotonation/protonation of coordinated secondary thioamide units of pincer ruthenium complexes: Modulation of voltammetric and spectroscopic characterization of the pincer complexes
  作者：Takuya Teratani、Take-aki Koizumi、Takakazu Yamamoto、Koji Tanaka、Takaki Kanbara

  DOI：10.1039/c0dt01283a

  日期：——

  New pincer ruthenium complexes, [Ru(SCS)(tpy)]PF6 (1) (SCS = 2,6-bis(benzylaminothiocarbonyl)phenyl), tpy = 2,2′:6′,2′'-terpyridyl) and [Ru(SNS)(tpy)]PF6 (2) (SNS = 2,5-bis(benzylaminothiocarbonyl)pyrrolyl), having κ3SCS and κ3SNS pincer ligands with two secondary thioamide units were synthesized by the reactions of [RuCl3(tpy)] with N,N'-dibenzyl-1,3-benzenedicarbothioamide (L1) and N,N'-dibenzyl-2,5-1H-pyrroledicarbothioamide (L2), respectively, and their chemical and electrochemical properties were elucidated. The structure of 1 was determined by X-ray crystallography. The complexes 1 and 2 showed a two-step deprotonation reaction by treatment with 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU), and the addition of DBU led to a shift of the metal-centered redox couples to a lower potential by 720 and 550 mV, respectively. The di-deprotonated complexes were also studied by 1H-NMR and UV-vis spectroscopy. The addition of methanesulfonic acid (MSA) to the di-deprotonated complexes enabled the recovery of 1 and 2, indicating that the thioamide moiety underwent a reversible deprotonation-protonation process, which resulted in regulating the redox potentials of the metal center. The Pourbaix diagram of 1 revealed that 1 underwent a one-proton/one-electron transfer process in the pH range of 5.83–10.35, and a two-proton/one-electron process at a pH of over 10.35, indicating that the deprotonation/protonation process of the complexes is related to proton-coupled electron transfer (PCET).

  新的钳形钌配合物[Ru(SCS)(tyy)]PF6 (1)（SCS = 2,6-双(苄氨基硫代羰基)苯基，tyy = 2,2′：通过[RuCl3(typy)]与 N、N'-二苄基-1,3-苯二硫代甲酰胺（L1）和 N,N'-二苄基-2,5-1H-吡咯烷二硫代甲酰胺（L2）反应合成了[RuCl3(tpy)]，并阐明了它们的化学和电化学性质。通过 X 射线晶体学确定了 1 的结构。配合物 1 和 2 经 1,8-二氮杂双环[5,4,0]十一-7-烯（DBU）处理后发生了两步去质子化反应，DBU 的加入导致以金属为中心的氧化还原偶分别向低电位移动了 720 mV 和 550 mV。二去质子化配合物还通过 1H-NMR 和 UV-vis 光谱进行了研究。在二去质子化的配合物中加入甲磺酸（MSA）后，1 和 2 得以恢复，这表明硫酰胺分子经历了可逆的去质子化-质子化过程，从而调节了金属中心的氧化还原电位。1 的 Pourbaix 图显示，1 在 pH 值为 5.83-10.35 的范围内经历了一个质子/一个电子转移过程，而在 pH 值超过 10.35 时则经历了一个双质子/一个电子转移过程，这表明配合物的去质子化/质子化过程与质子耦合电子转移（PCET）有关。
• Direct Transamidation of Thioamides with Amines via Acetophenone-Promoted Enamine Catalysis under Metal-Free Conditions
  作者：Yuxing Tan、Penghui Ni、Wu-jiu Jiang、Yang Fu、Qiuping Ding

  DOI：10.1021/acs.joc.3c02352

  日期：2024.3.1

  selective, efficient, and simple method for direct transamidation of thioamides with amines, promoted by commercially available acetophenone under metal-/solvent-free conditions. The reaction tolerated a wide range of functional groups and substrates, including single- or double-thioamides, benzylamines, or alkyl/cycloalkyl-substituted aliphatic amines. The present protocol can be applied to gram-scale in

  在此，我们开发了一种高选择性、高效且简单的方法，用于在无金属/溶剂的条件下通过市售苯乙酮促进硫代酰胺与胺的直接转酰胺基化。该反应可耐受多种官能团和底物，包括单硫代酰胺或双硫代酰胺、苄胺或烷基/环烷基取代的脂肪胺。本协议可以以良好的产量应用于克级。此外，双转酰胺基产物的 Pt-/Ni-配合物的产率也很高。光物理性质的研究表明，Pt配合物的荧光光谱显示出以550-750 nm为中心的发射带，并在紫外灯（365 nm）照射下呈现红色荧光。
• Nickel(II) complexes bearing a pincer ligand containing thioamide units: Comparison between SNS- and SCS-pincer ligands
  作者：Take-aki Koizumi、Takuya Teratani、Ken Okamoto、Takakazu Yamamoto、Yukihiro Shimoi、Takaki Kanbara

  DOI：10.1016/j.ica.2010.04.012

  日期：2010.8

  Nickel(II) complexes bearing a kappa(3)SNS pincer ligand, 2,5-bis(benzylaminothiocarbonyl)pyrrolyl (L1) and a kappa(3)SCS-pincer ligand, 2,6-bis(benzylaminothiocarbonyl)phenyl (L2), were synthesized, and their structures and electrochemical properties were elucidated. The crystal structures of [Ni(SNS)Br] (2) and [Ni(SCS)Br] (5) were determined by X-ray crystallography. The electrochemical and crystallographic data obtained from the complexes revealed that the kappa(3)SCS ligand has a stronger electron-donating ability than the kappa(3)SNS ligand. (C) 2010 Elsevier B.V. All rights reserved.