N-(1-苯基丙基)苯磺酰胺 | 861604-20-8

• 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-(1-苯基丙基)苯磺酰胺
• 英文名称: N-(1-phenylpropyl)benzenesulfonamide
• CAS: 861604-20-8
• 化学式: C₁₅H₁₇NO₂S
• 分子量: 275.371
• InChiKey: QFDHISYDRGWBLG-UHFFFAOYSA-N

物化性质

• 熔点：
  81 °C
• 沸点：
  419.7±38.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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-(1-苯基丙基)苯磺酰胺 在 次氯酸叔丁酯 、 lithium perchlorate 、 sodium sulfate 、 potassium bromide 作用下， 以 乙腈 为溶剂， 反应 21.5h， 生成 N-(1-cyano-1-phenylpropyl)benzenesulfonamide
  参考文献：
  名称：

  酰胺与甲硅烷基化亲核试剂通过N卤代反应的氮氧自由基催化氧化偶联

  摘要：

  带有N保护性吸电子基团（EWG）的胺与甲硅烷基化亲核试剂之间的硝酰-自由基催化的氧化偶联反应得以开发，可提供高收率的偶联产物，从而为有机催化反应开辟了新的领域。该反应通过硝酰自由基催化剂活化N卤代酰胺，然后与甲硅烷基化的亲核试剂进行碳-碳偶合。对反应机理的研究表明，硝酰基自由基可活化由N-EWG保护的酰胺和卤化试剂生成的N-卤代酰胺，生成相应的亚胺。

  DOI：

  10.1002/anie.201607223
• 作为产物：
  描述：

  三苯甲醛缩二胺 在 乙醚 作用下， 生成 N-(1-苯基丙基)苯磺酰胺
  参考文献：
  名称：

  Busch; Leefhelm, Journal fur praktische Chemie (Leipzig 1954), 1908, vol. <2>77, p. 22

  摘要：

  DOI：

文献信息

• Phytotoxic Activity of<i>N</i>-Benzylbenzenesulfonamides
  作者：Koichi Yoneyama、Nobumasa Ichizen、Hiroyoshi Omokawa、Yasutomo Takeuchi、Makoto Konnai、Tetsuo Takematsu

  DOI：10.1080/00021369.1984.10866170

  日期：1984.2

  A series of N-benzylbenzenesulfonamides were synthesized and their biological activities were tested. Among these compounds, N-(2,3-epoxypropyl)-N-(α-methylbenzyl)benzenesulfonamide derivatives were found to be the most active against barnyardgrass and to have physiological selectivity between barnyardgrass and rice plants.

  我们合成了一系列 N-苄基苯磺酰胺类化合物，并测试了它们的生物活性。在这些化合物中，N-(2,3-环氧丙基)-N-(α-甲基苄基)苯磺酰胺衍生物对稗草的活性最强，并且在稗草和水稻植物之间具有生理选择性。
• Selectfluor®-enabled photochemical selective C(sp³)–H(sulfonyl)amidation
  作者：Yuehua Chen、Boxuan Yang、Qian-Yu Li、Yu-Mei Lin、Lei Gong

  DOI：10.1039/d2cc05569d

  日期：——

  Transition metal- and photosensitizer-free C(sp3)–H (sulfonyl)amidation reactions have been realized by employing Selectfluor® as a versatile reagent, functioning as a photoactive component, a HAT precursor and an oxidant. Various toluene derivatives, cycloalkanes, natural products and bioactive molecules can be converted into N-containing products under mild conditions in good yield and with high

  通过使用 Selectfluor® 作为一种多功能试剂，实现了无过渡金属和光敏剂的 C(sp 3 )–H（磺酰基）酰胺化反应，作为光活性组分、HAT 前体和氧化剂。各种甲苯衍生物、环烷烃、天然产物和生物活性分子可以在温和条件下以高产率和高化学选择性和位点选择性转化为含氮产物。
• Nickel-catalysed addition of dialkylzinc reagents to N-phosphinoyl- and N-sulfonylimines
  作者：Raquel Almansa、David Guijarro、Miguel Yus

  DOI：10.1016/j.tet.2006.11.056

  日期：2007.1

  A catalytic amount of a nickel complex (0.1-5.3 mol %) extraordinarily increases the reaction rate of the addition of dialkylzinc reagents to N-(diphenylphosphinoyl)- or N-(benzenesulfonyl)imines. The reaction of imines derived from both aromatic and aliphatic aldehydes with various dialkylzinc reagents in the presence of several nickel complexes gives the expected addition products in most cases in I h and in very good yields. In general, the formation of reduction by-products was not an important side reaction. The process represents a great improvement, with regard to the reaction rate and the yield of the addition products, in comparison with the reactions performed in the absence of the nickel catalyst, and reaction times are much shorter than the ones reported so far using other catalysts. (c) 2006 Elsevier Ltd. All rights reserved.
• Chemoselective hydroamination of vinyl arenes catalyzed by an NHC-amidate-alkoxide Pd(II) complex and p-TsOH
  作者：Richard Giles、Justin O’Neill、Joo Ho Lee、Michael K. Chiu、Kyung Woon Jung

  DOI：10.1016/j.tetlet.2013.05.101

  日期：2013.7

  The hydroamination of various substituted vinyl arenes with benzenesulfonamide was explored using an NHC-amidate-alkoxide palladium catalyst in conjunction with p-TsOH. Utilizing halide-substituted and electron-rich vinyl arenes, this methodology selectively furnished the cross-coupled hydroamination products in moderate to excellent yields in a Markovnikov fashion while greatly reducing undesired acid-catalyzed homocoupling of the vinyl arenes. Electron-rich vinyl arenes typically required milder conditions than electron-poor ones. While most effective for para-substituted substrates, the catalyst system also furnished the desired products from ortho- and meta-substituted vinyl arenes with high chemoselectivities. (C) 2013 Elsevier Ltd. All rights reserved.