N-(2-amino-4,5-dimethylphenyl)phenylmethanesulfonamide | 400889-57-8

• 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-(2-amino-4,5-dimethylphenyl)phenylmethanesulfonamide
• 英文别名: N-benzylsulfonyl-4,5-dimethyl-o-phenylenediamine；N-benzylsulfonyl-4,5-dimethylbenzene-1,2-diamine；N-(2-Amino-4,5-dimethylphenyl)-1-phenylmethanesulfonamide
• CAS: 400889-57-8
• 化学式: C₁₅H₁₈N₂O₂S
• 分子量: 290.386
• InChiKey: FTBRUTVUILYJPC-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C(Solv: methanol (67-56-1))
• 沸点：
  469.8±55.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-amino-4,5-dimethylphenyl)phenylmethanesulfonamide 在 potassium carbonate 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 1.75h， 生成 C₃₆H₃₅BrN₂O₅S
  参考文献：
  名称：

  Tautomerism and Stereodynamics of Indophenols, Amidines, and Their Derivatives and Analogs: XVI. Synthesis of Tetrahydroquinoxalines Having Spiro-Fused Oxoindole and Cyclohepta[c]furan Fragments

  摘要：

  Alkylation of o-(N-sulfonylamino)phenylimino derivatives of indol-2-one and cyclohepta[c]furan with phenacyl bromides is accompanied by cyclization to previously unknown tetrahydroquinoxalines having spiro-fused oxoindole and cyclohepta[c]furan fragments. The structure of the latter includes a nitrogen-oxygen triangular system typical of most natural cytotoxic compounds.

  DOI：

  10.1023/b:rugc.0000039087.49416.5e
• 作为产物：
  描述：

  4，5-二甲基-1，2-苯二胺 、 苄磺酰氯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以50%的产率得到N-(2-amino-4,5-dimethylphenyl)phenylmethanesulfonamide
  参考文献：
  名称：

  Tautomerism and Stereodynamics of Indophenols, Amidines, and Their Derivatives and Analogs: XVI. Synthesis of Tetrahydroquinoxalines Having Spiro-Fused Oxoindole and Cyclohepta[c]furan Fragments

  摘要：

  Alkylation of o-(N-sulfonylamino)phenylimino derivatives of indol-2-one and cyclohepta[c]furan with phenacyl bromides is accompanied by cyclization to previously unknown tetrahydroquinoxalines having spiro-fused oxoindole and cyclohepta[c]furan fragments. The structure of the latter includes a nitrogen-oxygen triangular system typical of most natural cytotoxic compounds.

  DOI：

  10.1023/b:rugc.0000039087.49416.5e

文献信息

• Intramolecular π-complexes based on nitroaryl derivatives of furotroponimine: structure and stereodynamics
  作者：V. I. Minkin、A. V. Tkachuk、M. E. Kletskii、D. V. Steglenko、V. A. Voronina、S. V. Kurbatov

  DOI：10.1007/s11172-013-0065-6

  日期：2013.2

  Neutral aromatic electrophiles, such as trinitrobenzene and dinitrobenzofuroxane, covalently bound to the furotroponimine moiety form intramolecular through-space charge-transfer π-complexes both in solution and in the crystalline state. The kinetic and activation parameters of stereodynamic processes were determined by dynamic NMR spectroscopy. These parameters provide quantitative estimates of the kinetic stability of the p-complexes. The electronic and geometric characteristics of the π-complexes were calculated by the B3LYP/6-31G** method.

  中性芳香族亲电子试剂，例如三硝基苯和二硝基苯并呋喃，与呋托苯胺部分共价结合，在溶液和结晶状态下形成分子内通过空间电荷转移π-配合物。立体动力学过程的动力学和活化参数通过动态核磁共振波谱测定。这些参数提供了 p 配合物动力学稳定性的定量估计。 π配合物的电子和几何特征通过B3LYP/6-31G**方法计算。
• ——
  作者：V. I. Simakov、S. V. Kurbatov、O. Ya. Borbulevych、M. Yu. Antipin、L. P. Olekhnovich

  DOI：10.1023/a:1011333722238

  日期：——

  Condensation of ortho-aminophenols and N-benzylsulfonyl-o-phenylenediamine with nin-hydrin afforded tetracyclic products, the amino group entering into condensation with the carbonyl group at position 1 of ninhydrin. The structures of the reaction products were established by H-1 NMR spectroscopy and X-ray diffraction analysis.
• Tautomerism and Stereodynamics of Indophenols, Amidines, and Their Derivatives and Analogs: XVI. Synthesis of Tetrahydroquinoxalines Having Spiro-Fused Oxoindole and Cyclohepta[c]furan Fragments
  作者：S. V. Kurbatov、D. N. Kuznetsov、V. I. Simakov、V. A. Voronina、Yu. A. Zhdanov、L. P. Olekhnovich

  DOI：10.1023/b:rugc.0000039087.49416.5e

  日期：2004.5

  Alkylation of o-(N-sulfonylamino)phenylimino derivatives of indol-2-one and cyclohepta[c]furan with phenacyl bromides is accompanied by cyclization to previously unknown tetrahydroquinoxalines having spiro-fused oxoindole and cyclohepta[c]furan fragments. The structure of the latter includes a nitrogen-oxygen triangular system typical of most natural cytotoxic compounds.