N,N-dibutyl-N'-tosylformimidamide | 1071654-32-4

• 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-dibutyl-N'-tosylformimidamide
• 英文别名: N,N-dibutyl-N'-(4-methylphenyl)sulfonylmethanimidamide
• CAS: 1071654-32-4
• 化学式: C₁₆H₂₆N₂O₂S
• 分子量: 310.461
• InChiKey: LIIHUKJREYINQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三正丁胺 、 对甲苯磺酰氯 在 sodium azide 、 copper(ll) bromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以74%的产率得到N,N-dibutyl-N'-tosylformimidamide
  参考文献：
  名称：

  空气诱导的一锅从磺酰氯，NaN3和叔/仲胺合成N-磺酰基甲am

  摘要：

  在有氧氧化条件下，在DCE中存在5 mol％CuBr 2的情况下，使用容易获得的磺酰氯，叠氮化钠和叔/仲胺，在一个锅中合成了几种N-磺酰基甲am 。

  DOI：

  10.1002/ejoc.201901048

文献信息

• The C=C Bond Decomposition Initiated by Enamine‐Azide Cycloaddition for Catalyst‐ and Additive‐Free Synthesis of <i>N</i> ‐Sulfonyl Amidines
  作者：Xixi Zheng、Jie‐Ping Wan

  DOI：10.1002/adsc.201901054

  日期：2019.12.17

  The chemo‐selective synthesis of N‐sulfonyl amidines is realized via the decomposition of the enamine C=C bond of enaminoesters through an in situ generated triazoline intermediate. Control experiments prove that the electron withdrawing ester group in the enamine component is crucial in inducing the chemo‐selective formation of amidines. The method is featured with high efficiency and sustainability

  N-磺酰基am的化学选择性合成是通过原位生成的三唑啉中间体将烯胺酯的烯胺C = C键分解而实现的。对照实验证明，烯胺成分中的吸电子酯基对于诱导am的化学选择性形成至关重要。该方法以纯水为介质，无需任何催化剂或添加剂，具有高效，可持续的特点。
• Direct electrochemical imidation of aliphatic amines<i>via</i> anodic oxidation
  作者：Li Zhang、Ji-Hu Su、Sujing Wang、Changfeng Wan、Zhenggen Zha、Jiangfeng Du、Zhiyong Wang

  DOI：10.1039/c1cc10871a

  日期：——

  Direct electrochemical synthesis of sulfonyl amidines from aliphatic amines and sulfonyl azides was realized with good to excellent yields.

  直接电化学合成烷基胺和磺酰叠氮化合物，产率良好至优异。
• Catalyzed Imidation of Tertiary Amines by Simple Copper Salts
  作者：Nan Liu、Bo-Yang Tang、Yue Chen、Ling He

  DOI：10.1002/ejoc.200900143

  日期：2009.5

  Copper salt catalyzed imidation of tertiary amines by using sulfonyl azides as the nitrogen source was achieved with moderate to high yields. Formation of the carbon–nitrogen bond occurred chemoselectively with the use of a simple and inexpensive catalyst under moderate conditions, with a simple workflow, and with easy preparation of the nitrogen precursors.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  以磺酰叠氮化物为氮源，铜盐催化叔胺酰亚胺化，收率中等至高。碳氮键的形成是通过在温和条件下使用简单且廉价的催化剂、简单的工作流程和容易制备氮前体的化学选择性发生的。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim , 德国, 2009)
• Visible-light enabled room-temperature dealkylative imidation of secondary and tertiary amines promoted by aerobic ruthenium catalysis
  作者：Dong Yang、Jingqi Shi、Jiaming Chen、Xiaoqi Jia、Cuiying Shi、Lifang Ma、Ziyuan Li

  DOI：10.1039/d0ra10517a

  日期：——

  sulfonyl azide as a nitrogen donor, a visible-light-enabled aerobic dealkylative imidation of tertiary and secondary amines involving C(sp3)–C(sp3) bond cleavage with moderate to excellent yields at room temperature is described. It has been demonstrated that this imidation could take place spontaneously upon visible-light irradiation, and could be facilitated considerably by a ruthenium photocatalyst

  使用磺酰叠氮化物作为氮供体，描述了一种在可见光下对叔胺和仲胺进行有氧脱烷基化酰亚胺化，涉及 C(sp 3 )–C(sp 3 ) 键断裂，在室温下具有中等至优异的产率。已经证明，这种酰亚胺化可以在可见光照射下自发发生，并且可以通过钌光催化剂和氧气大大促进。还提出了先前需氧光氧化还原途径的替代机制。
• CuCl/CCl₄-Promoted Convenient Synthesis of Sulfonyl Amidines from Tertiary Amines and Sulfonyl Azides
  作者：Xiaoliang Xu、Zhichuang Ge、Dongping Cheng、Lei Ma、Chunshan Lu、Qunfeng Zhang、Nan Yao、Xiaonian Li

  DOI：10.1021/ol1000236

  日期：2010.3.5

  Promoted by CuCl/CCl4, a variety of sulfonyl azides and tertiary amines were successfully coupled to give sulfonyl amidine derivatives in good to excellent yields. A possible mechanism for this reaction is discussed.