N-methyl-2-(phenylsulfonyl)aniline | 53973-76-5

• 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-methyl-2-(phenylsulfonyl)aniline
• 英文别名: o-(methylamino)diphenyl sulfone；Phenyl-o-methylaminophenyl-sulfon；2-(benzenesulfonyl)-N-methylaniline
• CAS: 53973-76-5
• 化学式: C₁₃H₁₃NO₂S
• 分子量: 247.318
• InChiKey: AMJNIYXKOUQCJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  442.0±28.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methyl-2-(phenylsulfonyl)aniline 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 N,N-dimethyl-2-(phenylsulfonyl)aniline
  参考文献：
  名称：

  取代二苯砜的合成及其与5-НТ6受体拮抗作用的构效关系

  摘要：

  合成了取代的二苯砜（10a - n），并通过NMR，LC-MS和X射线晶体学证实了结构。在基于细胞的功能测定中评估了它们对5-HT 6受体的拮抗活性。尽管二苯砜10a是已知的最小和最简单的含磺酰基的5-HT 6 R拮抗剂，但仍显示出强大的效价（K i  = 1.6μM）。其具有甲胺取代基的衍生物10克（N-甲基-2-（苯磺酰基）苯胺）的活性是二苯砜的活性的66倍（K i  = 24.3 nM）。在其中添加哌嗪基部分相对于化合物10m中的磺酰基的对位（N-甲基-2-（苯基磺酰基）-5-哌嗪-1-基苯胺）导致效力进一步增加150倍（K i  = 0.16 nM），从而阻断了血清素诱导的人重组5-HT 6受体稳定转染的HEK-293细胞应答。

  DOI：

  10.1016/j.bmc.2013.05.040
• 作为产物：
  描述：

  2-(phenylsulfonylmethyl)pyridine 在 Dimethylammonium sulphite 作用下， 反应 24.0h， 生成 N-methyl-2-(phenylsulfonyl)aniline
  参考文献：
  名称：

  N-烷基-2-（苯磺酰基）苯胺合成的新途径

  摘要：

  这项工作的主要目的是研究在各种亲核试剂的存在下1-烷基-2-[（苯磺酰基）甲基]吡啶鎓碘化物的重排反应，从而产生N-烷基-2-（苯磺酰基）苯胺衍生物。用亚烷基磺酸铵可获得最佳结果，导致吡啶开环，然后环化以最高78％的收率得到二苯砜衍生物。

  DOI：

  10.1007/s10593-016-1933-4

文献信息

• Electron Beam-Induced Fries Rearrangement of Sulfonamide and Sulfonate Crystals
  作者：Jun Kato、Yasunari Maekawa、Masaru Yoshida

  DOI：10.1246/cl.2005.266

  日期：2005.2

  sensitivity of sulfonic acid derivatives in the crystalline state was much higher than that of the corresponding carboxylic acid derivatives, which was distinct from the results using other energy sources such as heat and UV; especially, sulfonamide derivatives could undergo the chemoselective Fries rearrangement to give ortho and para products in the ratio of ca. 7/3 without the meta isomer.

  结晶状态的磺酸衍生物的电子束（EB）灵敏度远高于相应的羧酸衍生物，这与使用其他能源如热和紫外线的结果不同；特别是，磺酰胺衍生物可以进行化学选择性 Fries 重排，以产生大约比例的邻位和对位产物。7/3 不含间位异构体。
• Urea derivatives as integrin a4 antagonists
  申请人：Jimenez Mayorga Miguel Juan

  公开号：US20070238763A1

  公开（公告）日：2007-10-11

  Novel antagonists of α4β1 integrin and/or α4β7 integrin are described in this application.

  本申请中描述了α4β1整合素和/或α4β7整合素的新型拮抗剂。
• Intermediacy of <i>o</i>-Sulfonylium Arenide Ylides in the Reactions of Arenesulfonyl Derivatives with Strong Bases:  Insight into the Puzzling Rearrangement of <i>N</i>-Arylarenesulfonamides into 2-Aminodiaryl Sulfones¹
  作者：John J. Eisch、Yun Qian、Chingchen S. Chiu

  DOI：10.1021/jo950727j

  日期：1996.1.1

  Benzenesulfonyl derivatives, PhSO(2)E, such as benzenesulfonyl fluoride, phenyl benzenesulfonate, and N-methyl-N-phenylbenzenesulfonamide, have been found to undergo ortho-lithiation with lithium 2,2,6,6-tetramethylpiperidide (LTMP) in THF at -78 degrees C. The resulting lithio derivatives undergo 1,3-elimination of LiE to form the transient o-sulfonylium benzenide. The latter ylide, which may be stabilized by its carbenoid character and its complexation with LiE, can be trapped by benzophenone acting as a 1,3-dipolarophile to form the adduct, 3,3-diphenyl-1,2-benzoxathiole 1,1-dioxide. The alternative formation of the latter cyclic sulfonate by reaction of the initially formed o-lithio derivative with benzophenone and by subsequent cyclization was shown not to occur. If not trapped with benzophenone, such an ylide decomposes partly into SO2 and benzyne and then undergoes self-condensation to yield poly(phenylene-o,o'-biphenylene sulfones), o-Sulfonylium benzenide also can be captured by lithium alkoxides, either present adventitously or intentionally added, to generate the corresponding alkyl benzenesulfonate. However, such alkoxides, unaided by LTMP, are themselves unable to extract an ortho-proton from benzenesulfonyl fluoride or from N-methyl-N-phenylbenzenesulfonamide to yield the corresponding o-lithio derivative. With benzenesulfonyl fluoride the lithium alkoxide can also form the sulfonate ester by direct substitution at the sulfonyl group. The Closson-Hellwinkel rearrangement of N-methyl-N-phenylbenzenesulfonamide into o-(methylamino)diphenyl sulfone by RLi or LTMP is reinterpreted as proceeding by way of the 2-lithio- or 2,6-dilithiobenzenesulfonyl derivative which eliminates lithium N-methylanilide to form the o-sulfonylium benzenide or its 6-lithio derivative. Attack of the latter ylide, acting as an electrophile, upon the ortho-position of the presumably complexed LiNMePh then consummates the rearrangement.
• Photofunctional optical material comprising fluorine-containing acrylate polymer
  申请人：Ando Yoshito

  公开号：US20070197718A1

  公开（公告）日：2007-08-23

  There is provided the photofunctional optical material which is excellent in an intensity of light emission, light emitting efficiency and/or light amplifying property and also is excellent in processability, for example, easy processing into an optical waveguide device. The photofunctional optical material contains a fluorine-containing acrylate, a polyfunctional acrylate and a rare earth metal compound. There is also provided the composition containing a fluorine-containing acrylate, a polyfunctional acrylate and a rare earth metal compound and is suitable for an optical material.
• US7253171B2
  申请人：——

  公开号：US7253171B2

  公开（公告）日：2007-08-07