N-(bis(cyclohexylamino)methylene)-1,1,1-trifluoromethanesulfonamide | 1338440-24-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-(bis(cyclohexylamino)methylene)-1,1,1-trifluoromethanesulfonamide
• 英文别名: N-[bis(cyclohexylamino)methylidene]-1,1,1-trifluoromethanesulfonamide；1,3-dicyclohexyl-2-(trifluoromethylsulfonyl)guanidine；1,2-dicyclohexyl-3-(trifluoromethylsulfonyl)guanidine
• CAS: 1338440-24-6
• 化学式: C₁₄H₂₄F₃N₃O₂S
• 分子量: 355.425
• InChiKey: BZKAHHZEBXPPJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(bis(cyclohexylamino)methylene)-1,1,1-trifluoromethanesulfonamide 、 双三氟甲烷磺酰亚胺 以 二氯甲烷 为溶剂， 反应 6.0h， 以100%的产率得到bis(cyclohexylamino)-N-[(trifluoromethyl)sulfonyl]methaniminium bis[(trifluoromethyl)sulfonyl]azanide
  参考文献：
  名称：

  Synthesis and structure of N-(diaminomethylidene)- and N-[bis(cyclohexylamino)methylidene]trifluoromethanesulfonamides

  摘要：

  N-Trifluoromethylsulfonyl-substituted guanidines CF3SO2N=C(NHR)(2) (R = H, cyclohexyl) were synthesized in nearly quantitative yield by reactions of N-sulfinyltrifluoromethanesulfonamide CF3SO2N=S=O with urea and of trifluoromethanesulfonamide with N,N'-dicyclohexylcarbodiimide. N-[Bis(cyclohexylamino)-methylidene]trifluoromethanesulfonamide was subjected to protonation with trifluoromethanesulfonic acid and bis(trifluoromethanesulfonyl)imide, and the structure of the resulting salts and initial N-trifluoromethylsulfonylguanidines was studied by NMR and IR spectroscopy and DFT quantum-chemical calculations.

  DOI：

  10.1134/s1070428011090028
• 作为产物：
  描述：

  N-trifluoromethanesulfonyl-2,4-dicyclohexyl-1,2,4-thiadiazetidin-3-imine 1-oxide 在 水 作用下， 反应 0.67h， 以95%的产率得到N-(bis(cyclohexylamino)methylene)-1,1,1-trifluoromethanesulfonamide
  参考文献：
  名称：

  碳二亚胺向N-烯基亚内三氟化合物的异常[2 + 2]-环加成

  摘要：

  使用1，3 - N-三氟甲基磺酰基-1-氮杂丁二烯与碳二亚胺的示例反应，首次观察到1-氮杂二烯的C C键具有不寻常的[2 + 2] -环加成。由二环己基碳二亚胺和N-（3-甲基丁-2-烯-1-亚烷基）形成的N -{[2,2-二甲基-1-环己基-4-（环己基氨基））氮杂环丁烷-3-亚丙基]甲基}三氟甲磺酰胺的结构三氟甲磺酰胺经单晶X射线分析证实。

  DOI：

  10.1016/j.tetlet.2016.08.078

文献信息

• Development of CN Coupling Using Mechanochemistry: Catalytic Coupling of Arylsulfonamides and Carbodiimides
  作者：Davin Tan、Cristina Mottillo、Athanassios D. Katsenis、Vjekoslav Štrukil、Tomislav Friščić

  DOI：10.1002/anie.201404120

  日期：2014.8.25

  sulfonyl guanidines, a family of molecules which are relevant as pharmaceuticals and herbicides, by direct coupling of sulfonamides and aromatic or aliphatic carbodiimides. Attempts to conduct the coupling in solution have either failed or given very low conversions, thus demonstrating mechanochemistry as the necessary component for the discovery of this synthetic strategy.

  本文报道的是通过磺酰胺与芳族或脂族碳二亚胺的直接偶联，磺酰胍的机械化学合成，磺酰胍是与药物和除草剂有关的分子家族。在溶液中进行偶联的尝试要么失败，要么转化率非常低，因此证明了机械化学是发现这种合成策略的必要组成部分。
• Simple methods for the preparation of N-triflyl guanidines and the structure of compounds with the CF3SO2NCN fragment
  作者：Bagrat A. Shainyan、Ljudmila L. Tolstikova、Uwe Schilde

  DOI：10.1016/j.jfluchem.2011.12.004

  日期：2012.3

  Two novel and simple approaches to N-triflyl guanidines are elaborated. Owing to very strong conjugation the formally double CN bond of TfNC(NHR)2 is longer than the formally single NC bonds. Energetic effect of the triflyl group on the conjugation in the NCN moiety is estimated to be ≥150 kcal/mol.

  阐述了两种新颖且简单的N-三氟鸟胍的方法。由于非常强的共轭，TfN C（NHR）2的形式上双C N键比形式上单个N C键长。Triflyl基团对N C N部分的共轭作用的能量作用估计为≥150kcal / mol。
• Reaction of N-sulfinyltrifluoromethanesulfonamide with carbodiimides: Formation of N-trifluoromethanesulfonyl-2,4-dialkyl-1,2,4-thiadiazetidin-3-imine 1-oxides
  作者：Bagrat A. Shainyan、Ljudmila L. Tolstikova

  DOI：10.1016/j.jfluchem.2012.04.016

  日期：2012.8

  N-sulfinyltrifluoromethanesulfonamide was found to react with diisopropyl- and dicyclohexylcarbodiimides with the formation of N-trifluoromethanesulfonyl-2,4-dialkyl-1,2,4-thiadiazetidin-3-imine 1-oxides. The mechanism includes the [2 pi + 2 pi] cycloaddition resulting in 2-trifluoromethanesulfonyl-3-alkylimino-4-alkyl-1,2,4-thiadiazetidine 1-oxides, the ring opening of the latter, rotation about the C-N bond and the ring closure to the final products. (C) 2012 Elsevier B.V. All rights reserved.
• ACTINIC RAY-SENSITIVE OR RADIATION-SENSITIVE RESIN COMPOSITION, AND RESIST FILM AND PATTERN FORMING METHOD USING THE SAME
  申请人：HIRANO Shuji

  公开号：US20120003590A1

  公开（公告）日：2012-01-05

  An actinic ray-sensitive or radiation-sensitive resin composition containing a resin having (A) a repeating unit represented by a specific formula (I) and (B) a repeating unit capable of generating an acid upon irradiation with an actinic ray or radiation.
• ACTINIC-RAY- OR RADIATION-SENSITIVE RESIN COMPOSITION, ACTINIC-RAY- OR RADIATION-SENSITIVE FILM THEREFROM AND METHOD OF FORMING PATTERN
  申请人：FUJIFILM CORPORATION

  公开号：US20140227636A1

  公开（公告）日：2014-08-14

  Provided is an actinic-ray- or radiation-sensitive resin composition including a resin (Aa) containing at least one repeating unit (Aa1) derived from monomers of general formula (aa1-1) below and at least one repeating unit (Aa2) derived from monomers of general formula (aa2-1) below and comprising a resin (Ab) that when acted on by an acid, changes its alkali solubility.