(R/S)-2-nitro-N-(1-phenylethyl)benzenesulfonamide

• 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: (R/S)-2-nitro-N-(1-phenylethyl)benzenesulfonamide
• 英文别名: 2-nitro-N-(1-phenylethyl)benzenesulfonamide；2-nitro-benzenesulfonic acid-(1-phenyl-ethylamide)；2-Nitro-benzolsulfonsaeure-(1-phenyl-aethylamid)
• 化学式: C₁₄H₁₄N₂O₄S
• 分子量: 306.342
• InChiKey: ZHYXXNPABNYAJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R/S)-2-nitro-N-(1-phenylethyl)benzenesulfonamide 在 polystyrene-thiophenol 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以96%的产率得到α-苯乙胺
  参考文献：
  名称：

  Deprotection of o-Nitrobenzensulfonyl (Nosyl) Derivatives of Amines ­Mediated by a Solid-Supported Thiol

  摘要：

  研究人员开发了一种基于固体支撑硫醇的新方案，用于对伯胺和仲胺衍生的邻硝基苯磺酰基酰胺进行高产率脱保护。反应可在室温下进行 24 小时，也可通过微波辐照加速，在 6 分钟内完成。

  DOI：

  10.1055/s-2005-921892
• 作为产物：
  描述：

  乙基苯 、 2-硝基苯磺酰胺 在 Rh₂(esp)2 二(叔丁基羰基氧基)碘苯 作用下， 以 苯 为溶剂， 以29%的产率得到(R/S)-2-nitro-N-(1-phenylethyl)benzenesulfonamide
  参考文献：
  名称：

  Catalytic Intermolecular Amination of C−H Bonds: Method Development and Mechanistic Insights

  摘要：

  y Reaction methodology for intermolecular C-H amination of benzylic and 3 degrees C-H bonds is described. This process uses the starting alkane as the limiting reagent, gives optically pure tetrasubstituted amines through stereospecific insertion into enantiomeric 3 degrees centers, displays high chemoselectivity for benzylic oxidation, and enables the facile preparation of isotopically enriched N-15-labeled compounds. Access to substituted amines, amino alcohols, and diamines is thereby made possible in a single transformation. Important information relevant to understanding the initial steps in the catalytic cycle, reaction chemoselectivity, the nature of the active oxidant, and pathways for catalyst inactivation has been gained through mechanistic analysis; these studies are also presented.

  DOI：

  10.1021/ja0650450

文献信息

• Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions
  作者：Daniel R. Wallach、John D. Chisholm

  DOI：10.1021/acs.joc.6b01421

  日期：2016.9.2

  with trichloroacetimidates is reported. This transformation does not require an exogenous acid, base, or transition metal catalyst; instead the addition occurs in refluxing toluene without additives. The sulfonamide alkylation partner appears to be only limited by sterics, with unsubstituted sulfonamides providing better yields than more encumbered N-alkyl sulfonamides. The trichloroacetimidate alkylating

  据报道，磺酰胺与三氯乙酰亚胺的分子间烷基化。该转化不需要外源酸，碱或过渡金属催化剂；取而代之的是在没有添加剂的情况下在回流甲苯中进行添加。磺酰胺烷基化伙伴似乎仅受空间限制，未取代的磺酰胺比负担更大的N-烷基磺酰胺提供更好的产率。三氯乙酰亚胺酸酯烷基化剂必须是稳定的阳离子前体，才能在这些条件下进行取代反应。
• N-(2,3-Epoxypropylene)-n-aralkylsulfonamide and herbicidal compositions
  申请人：Mitsubishi Chemical Industries Ltd.

  公开号：US04468245A1

  公开（公告）日：1984-08-28

  An N-(2,3-epoxypropylene)-N-aralkylsulfonamide of formula (I): ##STR1## wherein R.sup.1 is an alkyl group, a haloalkyl group, an aralkyl group or an aryl group which may be substituted, R.sup.2 and R.sup.3, independently of each other, are a hydrogen atom or an alkyl group, R.sup.4 and R.sup.4', independently of each other, are a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, R.sup.5, R.sup.6 and R.sup.7, independently of each other, are a hydrogen atom, an alkyl group, a haloalkyl group or an aryl group, and n is 0 or 1. The novel compounds have excellent herbicidal effect based on the physiological selectivity between rice plant and weeds, and have low phytotoxicity against rice plant.

  化学式为(I)的N-(2,3-环氧丙烷基)-N-芳基磺酰胺，其中R1是烷基，卤代烷基，芳基烷基或取代的芳基基团，R2和R3独立地是氢原子或烷基基团，R4和R4'独立地是氢原子，烷基基团，烷氧基或卤素原子，R5，R6和R7独立地是氢原子，烷基基团，卤代烷基或芳基基团，n为0或1。这些新化合物具有基于水稻植物和杂草之间的生理选择性的优异除草效果，并对水稻植物的光毒性较低。
• Discovery of Salermide-Related Sirtuin Inhibitors: Binding Mode Studies and Antiproliferative Effects in Cancer Cells Including Cancer Stem Cells
  作者：Dante Rotili、Domenico Tarantino、Angela Nebbioso、Chantal Paolini、Covadonga Huidobro、Ester Lara、Paolo Mellini、Alessia Lenoci、Riccardo Pezzi、Giorgia Botta、Maija Lahtela-Kakkonen、Antti Poso、Christian Steinkühler、Paola Gallinari、Ruggero De Maria、Mario Fraga、Manel Esteller、Lucia Altucci、Antonello Mai

  DOI：10.1021/jm3011614

  日期：2012.12.27

  Chemical changes performed on 1a (sirtinol) led to a series of SIRT1/2 inhibitors, in some cases more potent than la mainly against SIRT1. Tested in human leukemia U937 cells, the benzamide and anilide derivatives 1b, 1c, 2b, and 2c as well as the 4-(2-phenylpropyl)thioanalogue 4c showed huge apoptosis induction, while some sulfinyl and sulfonyl derivatives (5b, 5c, and 6a-c) were highly efficient in granulocytic differentiation. When assayed in human leukemia MOLT4 as well as in human breast MDA-MB-231 and colon RKO cancer cell lines, the anilide 2b (salermide) and the phenylpropylthio analogue 4b emerged as the most potent antiproliferative agents. Tested on colorectal carcinoma and glioblastoma multiforme cancer stem cells (CSCs) from patients, 2b was particularly potent against colorectal carcinoma CSCs, while 4b, 6a, and the SIRT2-selective inhibitor AGK-2 showed the highest effect against glioblastoma multiforme CSCs. Such compounds will be further explored for their broad-spectrum anticancer properties.
• US4468245A
  申请人：——

  公开号：US4468245A

  公开（公告）日：1984-08-28
• Catalytic Intermolecular Amination of C−H Bonds: Method Development and Mechanistic Insights
  作者：Kristin Williams Fiori、J. Du Bois

  DOI：10.1021/ja0650450

  日期：2007.1.1

  y Reaction methodology for intermolecular C-H amination of benzylic and 3 degrees C-H bonds is described. This process uses the starting alkane as the limiting reagent, gives optically pure tetrasubstituted amines through stereospecific insertion into enantiomeric 3 degrees centers, displays high chemoselectivity for benzylic oxidation, and enables the facile preparation of isotopically enriched N-15-labeled compounds. Access to substituted amines, amino alcohols, and diamines is thereby made possible in a single transformation. Important information relevant to understanding the initial steps in the catalytic cycle, reaction chemoselectivity, the nature of the active oxidant, and pathways for catalyst inactivation has been gained through mechanistic analysis; these studies are also presented.