N-(2,6-二甲基苯基)苯磺酰胺 | 16939-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2,6-二甲基苯基)苯磺酰胺
• 英文名称: N-(2,6-dimethylphenyl)-benzene sulfonamide
• 英文别名: benzenesulfonic acid-(2,6-dimethyl-anilide)；Benzolsulfonsaeure-(2,6-dimethyl-anilid)；N-2,6-Dimethylphenylbenzolsulfonamid；Benzolsulfon-N-(2,6-xylyl)-amid；N-(2,6-dimethylphenyl)benzenesulfonamide
• CAS: 16939-27-8
• 化学式: C₁₄H₁₅NO₂S
• mdl: MFCD00091027
• 分子量: 261.345
• InChiKey: NRCQXFJDFRLCCW-UHFFFAOYSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  393.9±52.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  N-(2,6-二甲基苯基)苯磺酰胺 在 硫酸 作用下， 生成 2,6-二甲基-3-硝基苯胺
  参考文献：
  名称：

  Wepster, Recueil des Travaux Chimiques des Pays-Bas, 1954, vol. 73, p. 809,815

  摘要：

  DOI：
• 作为产物：
  描述：

  苯磺酰氯 、 2,6-二甲基苯胺 以 水 为溶剂， 生成 N-(2,6-二甲基苯基)苯磺酰胺
  参考文献：
  名称：

  二甲基[甲基（苯磺酰基）氨基]苯磺酰氯的两种新的空间位阻异构形式的合成、晶体和分子电子结构以及动力学研究

  摘要：

  摘要 合成了两种新的结构异构体——2,4-二甲基-5-[甲基(苯磺酰基)氨基]苯磺酰氯(1)和2,4-二甲基-3-[甲基(苯磺酰基)氨基]苯磺酰氯(2) N-(2,4-二甲基苯基)-N-甲基-苯磺酰胺或N-(2,6-二甲基苯基)-N-甲基苯磺酰胺与氯磺酸的相互作用。两种化合物均已通过 100 K 下的 X 射线单晶衍射进行结构表征。 1 的晶体为三斜晶系：空间群 P 1 ¯ , a = 8.1542(2), b = 11.0728(3), c = 11.2680(3) A, α = 116.557(3), β = 95.155(2), γ = 108.258(2)°, V = 831.97(4) A3, Z = 2, R = 0.0251 2429 次反射；2的晶体为单斜晶系：空间群P21/c, a = 11.7428(2), b = 11.3518(2), c = 12.5886(2) A

  DOI：

  10.1016/j.molstruc.2017.02.016

文献信息

• Synthesis and Dynamic NMR Study of a Functionalized Sulfonamide Phosphonate Diester
  作者：Faramarz Rostami Charati、Masoumeh Moghimi、Malek Taher Maghsoodlou、Sayyed M. Habibi-Khorassani、Zinatossadat Hossaini、Nariman Maleki、Brian W. Skelton、Mohamed Makha

  DOI：10.1080/10426507.2010.515951

  日期：2011.7.1

  leads to a phosphonate ylide, which undergoes methanol elimination in the presence of moisture to produce a highly functionalized sulfonamide phosphonate diester. A dynamic nuclear magnetic resonance (NMR) effect is observed in the 1H NMR spectra of this compound as a result of restricted rotation around the single C‒N bond. The coalescence temperature was observed at TC = 352.5 K, and the free energy

  摘要 亚磷酸三苯酯与活化乙炔通过磺酰胺反应生成的高反应性 1:1 中间体质子化生成膦酸酯叶立德，在水分存在下通过甲醇消除生成高度官能化的磺酰胺膦酸二酯。由于围绕单个 C-N 键的旋转受限，在该化合物的 1H NMR 光谱中观察到动态核磁共振 (NMR) 效应。在 TC = 352.5 K 时观察到聚结温度，该过程的活化自由能 (ΔG#) 为 75.6 ± 2 kJ.mol-1。图形概要
• Efficient Synthesis of Stable Phosphonate Ylides and Phosphonate Esters: Reaction Between Activated Acetylenes and Triphenylphosphite in the Presence of Sulfonamide and Heterocyclic NH-Acids
  作者：Faramarz Rostami Charati、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Nourallah Hazeri、Ali Ebrahimi、Zinatossadat Hossaini、Pouneh Ebrahimi、Nariman Maleki、Sayyed Reza Adhamdoust、Fatemeh Vasheghani-Farahani、Ghasem Marandi、Alexandre Sobolev、Mohamed Makha

  DOI：10.2174/1386207311107010002

  日期：2011.1.1

  efficient synthesis of stable phosphonate ylides and phosphonate esters is described via a ‎one-pot reaction between activated acetylenes and triphenylphosphite in the presence of sulfonamides and heterocyclic ‎NH-acids. Single X-ray diffraction analysis and NMR studies were used in characterizing the ylides and phosphonate ester products. Dynamic NMR studies performed on a phosphonate ylide allowed the calculation

  通过活化的乙炔与亚磷酸三苯酯在磺酰胺和杂环NH-酸的存在下的一锅法反应，描述了稳定的膦酸酯基化物和膦酸酯的有效合成。单次X射线衍射分析和NMR研究用于表征酰基化物和膦酸酯产物。对膦酸酯内酯进行的动态NMR研究允许计算自由能垒，用于几何异构体（E）和（Z）之间的相互转化。
• Polymorphism in Secondary Benzene Sulfonamides
  作者：Palash Sanphui、Bipul Sarma、Ashwini Nangia

  DOI：10.1021/cg100845f

  日期：2010.10.6

  The role of about 20 different solvents in the crystallization of polymorphs for 13 N-phenyl benzene sulfonamides was studied. Five compounds (1, 2, 3, 7, and 11) are dimorphic, and one is trimorphic (6). All the crystalline solids were characterized by powder and single crystal X-ray diffraction, thermal analysis, hot stage microscopy, and IR and Raman spectroscopy. The phase transition from a metastable form to the stable form was examined visually for two compounds (1, 11) on a HSM and confirmed by differential scanning calorimetry and X-ray diffraction. The N-H center dot center dot center dot O hydrogen bond catemer (chain) and dimer (cyclic) motifs of the sulfonamide group were analyzed as the main difference between polymorphs of 1, 3, and 6. Weaker C-H center dot center dot center dot O interactions differentiate the molecular packing of other polymorphic systems. Accordingly, these crystal structures are referred to as synthon polymorphs. The occurrence of N-H center dot center dot center dot O catemer and dimer synthon in secondary sulfonamides is compared with crystal structures in the Cambridge database. The nearly equal probability of the dimer and catemer motifs for secondary sulfonamides (similar to 19%) is attributed to the possibility of making the catemer synthon via both anti and syn oxygen atoms of the SO(2)NH group, with the former acceptor being preferred in two-thirds of the cases.
• Dauphin,G. et al., Bulletin de la Societe Chimique de France, 1967, p. 3404 - 3410
  作者：Dauphin,G. et al.

  DOI：——

  日期：——
• Design, synthesis and structure–activity relationship of new HSL inhibitors guided by pharmacophore models
  作者：Jumana D. Al-Shawabkeh、Afaf H. Al-Nadaf、Lina A. Dahabiyeh、Mutasem O. Taha

  DOI：10.1007/s00044-013-0616-2

  日期：2014.1

  Hormone-sensitive lipase (HSL) is a critical enzyme involved in the hormonally regulated release of fatty acids and glycerol from adipocyte lipid stores. Its inhibition may improve insulin sensitivity and blood glucose handling in type 2 diabetes. Accordingly, many small-molecule HSL inhibitors have recently been identified. In continuation of our efforts for discovery of new HSL inhibitors, we prepared a variety of esters, amides, sulfonamides and sulfonate esters capable of fitting two pharmacophore models that we developed and published earlier. The tested compounds were synthesized via coupling reactions of aroyl chlorides or sulfonyl chlorides with phenols, amines and related derivatives. Our efforts led to the identification of interesting compounds of low micromolar anti-HSL bioactivities, which have potential to be developed into effective antidiabetic agents.