N,N-Dimethyl-3,5-dinitro-thiobenzamide | 518068-02-5

• 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-Dimethyl-3,5-dinitro-thiobenzamide
• 英文别名: N,N-Dimethyl-3,5-dinitrobenzene-1-carbothioamide；N,N-dimethyl-3,5-dinitrobenzenecarbothioamide
• CAS: 518068-02-5
• 化学式: C₉H₉N₃O₄S
• 分子量: 255.254
• InChiKey: UKAYCIQTLYBYMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-Dimethyl-3,5-dinitro-thiobenzamide 在 2,2'-bipyridinium chlorochromate 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以98%的产率得到N,N-dimethyl-3,5-dinitrobenzamide
  参考文献：
  名称：

  使用3-羧吡啶鎓和2,2'-联吡啶鎓氯代铬酸盐在溶液，干燥介质中和微波辐射下高效简便地将硫羰基脱保护为羰基化合物

  摘要：

  报道了3-羧基吡啶鎓（ CPCC ）和2,2'-联吡啶鎓（ BPCC）氯铬酸盐 在脱保护反应中的合成效用 。用这些试剂将不同类型的硫代酰胺，硫脲，硫代酸酯和硫代酮以良好或优异的产率脱保护为其相应的羰基化合物。反应在溶液中，无溶剂条件下和在微波辐射下进行。结果表明，在微波辐射下，两种试剂的反应速率和产率通常最高。

  DOI：

  10.1007/s00706-003-0095-0

文献信息

• A Convenient and Inexpensive Method for Conversion of Thiocarbonyl Compounds to Their Oxo Derivatives Using Oxone Under Solvent-Free Conditions
  作者：Iraj Mohammadpoor-Baltork、Majid M. Sadeghi、Karim Esmayilpour

  DOI：10.1081/scc-120016359

  日期：2003.1.4

  Abstract A series of thioamides, thioureas and thioesters are transformed to their corresponding carbonyl compounds in good to excellent yields with oxone under solid phase conditions, while thioketones remained unchanged under these conditions.

  摘要 一系列硫代酰胺、硫脲和硫酯在固相条件下与 oxone 一起转化为相应的羰基化合物，产率良好至极好，而硫酮在这些条件下保持不变。
• Transformation of Thioamide Compounds to Corresponding Amides Using 12-Tungstosilicic Acid
  作者：Masoud Nasr-Esfahani、Morteza Montazerozohori、Majid Moghadam、Iraj Mohammadpoor-Baltork、Sareh Moradi

  DOI：10.1080/10426500902758964

  日期：2010.1.29

  12-Tungstosilicic acid (H4SiW12O40) is applied for the conversion of a series of thioamides to their corresponding oxo analogues in excellent yields in acetonitrile. In the case of thioketones, no reaction is observed under these conditions. The reusability of the catalyst also is investigated.

  12-钨硅酸 (H4SiW12O40) 用于在乙腈中以极好的收率将一系列硫代酰胺转化为其相应的氧代类似物。在硫酮的情况下，在这些条件下没有观察到反应。还研究了催化剂的可重复使用性。
• Bismuth(III) nitrate pentahydrate: a convenient and selective reagent for conversion of thiocarbonyls to their carbonyl compounds
  作者：Iraj Mohammadpoor-Baltork、Mohammad Mehdi Khodaei、Kobra Nikoofar

  DOI：10.1016/s0040-4039(02)02516-9

  日期：2003.1

  A variety of thioamides and thioureas are rapidly transformed to their oxo derivatives with Bi(NO3)3·5H2O in excellent yields. However, thiono esters and thioketones are converted to their corresponding carbonyl compounds in only poor yields. Bi(NO3)3·5H2O is relatively non-toxic, insensitive to air and inexpensive. These features coupled with the selective deprotection of thioamides and thioureas

  各种硫代酰胺和硫脲可通过Bi（NO 3）3 ·5H 2 O迅速转化为它们的oxo衍生物，收率很高。然而，硫代酸酯和硫代酮仅以低收率转化为它们相应的羰基化合物。Bi（NO 3）3 ·5H 2 O相对无毒，对空气不敏感且价格便宜。这些特征与在硫代酸酯和硫代酮的存在下硫代酰胺和硫脲的选择性脱保护相结合，使得该方法成为现有的脱硫羰基化合物脱保护途径的有吸引力的替代方法。
• A Mild and Convenient Method for Conversion of Thioamides to Their Corresponding Amides Using Acidified Wet Silica-Supported Permanganate Under Solvent-Free Conditions
  作者：Masoud Nasr-Esfahani、Majid Moghadam、Iraj Mohammadpoor-Baltork、Mohammad Hasan Boostanifar

  DOI：10.1080/10426500802080865

  日期：2008.12.23

  A mild and efficient method for conversion of thioamides to their corresponding amides is reported. A series of thioamides are transformed to their corresponding carbonyl compounds in good to excellent yields by acidified wet silica-supported permanganate under solid phase conditions.
• A Facile and Convenient Method for Deprotection of Thiocarbonyls to Their Carbonyl Compounds Using Oxone Under Aprotic and Nonaqueous Conditions
  作者：I. Mohammadpoor-Baltork、M. M. Sadeghi、K. Esmayilpour

  DOI：10.1080/10426500307781

  日期：2003.1.1

  The reaction of oxone as an inexpensive, stable, and commercially available reagent with thiocarbonyl compounds in refluxing acetonitrile has been studied. Primary, secondary, and tertiary thioamides and thioureas are converted to their oxo analogues efficiently. Thiono esters also are transformed to their corresponding esters, while thioketones remained intact under these conditions.