3-nitro-4-((2-(prop-1-en-2-yl)phenyl)amino)benzenesulfonic acid | 918297-95-7

• 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: 3-nitro-4-((2-(prop-1-en-2-yl)phenyl)amino)benzenesulfonic acid
• 英文别名: 4-nitro-N-(2-(prop-1-en-2-yl)phenyl)benzenesulfonamide；4-Nitro-N-[2-(prop-1-en-2-yl)phenyl]benzene-1-sulfonamide；4-nitro-N-(2-prop-1-en-2-ylphenyl)benzenesulfonamide
• CAS: 918297-95-7
• 化学式: C₁₅H₁₄N₂O₄S
• 分子量: 318.353
• InChiKey: PLHLJODPJZWTCO-UHFFFAOYSA-N

物化性质

• 沸点：
  489.0±55.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  3-nitro-4-((2-(prop-1-en-2-yl)phenyl)amino)benzenesulfonic acid 在 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以86%的产率得到3-methyl-N-p-nitrobenzenesulfonylindole
  参考文献：
  名称：

  Novel formation of indoles and 3,1-benzoxazines from o-alkenylanilides and dimethyl(methylthio)sulfonium trifluoromethanesulfonate

  摘要：

  The reaction of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) with o-allylphenol gave 2-methylthiomethyl-2,3-dihydrobenzofuran in 97% yield. The reaction of DMTST with N-tosyl-o-isopropenylanilide followed by the addition of aq sodium carbonate afforded N-tosyl-3-methylindole in 88% yield, whereas N-tosyl-o-vinylanilide afforded N-tosylindoline in 85% yield. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.05.111
• 作为产物：
  描述：

  1-硝基-2-丙-1-烯-2-基苯 在 sodium thiosulfate 作用下， 生成 3-nitro-4-((2-(prop-1-en-2-yl)phenyl)amino)benzenesulfonic acid
  参考文献：
  名称：

  Novel formation of indoles and 3,1-benzoxazines from o-alkenylanilides and dimethyl(methylthio)sulfonium trifluoromethanesulfonate

  摘要：

  The reaction of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) with o-allylphenol gave 2-methylthiomethyl-2,3-dihydrobenzofuran in 97% yield. The reaction of DMTST with N-tosyl-o-isopropenylanilide followed by the addition of aq sodium carbonate afforded N-tosyl-3-methylindole in 88% yield, whereas N-tosyl-o-vinylanilide afforded N-tosylindoline in 85% yield. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.05.111

文献信息

• Regioselective Synthesis of Benzazetines and Indoles from Alkenylanilides and Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate
  作者：Kentaro Okuma、Itsuki Takeshita、Takumi Yasuda、Kosei Shioji

  DOI：10.1246/cl.2006.1122

  日期：2006.10

  Regioselective synthesis of benzazetines and indoles from o-alkenylanilides was achieved. The reaction of o-vinylbenzanilide with dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) gave the corresponding benzazetine in 92% yield, whereas the reaction of o-vinyl-N-p-toluenesulfonylanilide gave N-tosylindoline in 77% yield. 3-Methy-N-p-tosylindole was directly synthesized by the reaction of o-isopropenyl-N-p-tosylanilide with dimethyl disulfide and methyl triflate in 85% yield.

  实现了从邻烯基苯胺酸酯选择性合成苯并吖庚因和吲哚。邻乙烯基苯并苯胺酸酯与二甲基（甲硫基）硫镨三氟甲磺酸盐（DMTST）反应得到相应苯并吖庚因，产率达92%；而邻乙烯基-N-对甲苯磺酰苯胺酸酯反应得到N-对甲苯磺酰吲哚啉，产率达77%。通过邻异丙烯基-N-对甲苯磺酰苯胺酸酯与二甲基二硫和甲基三氟甲磺酸盐反应，可直接合成3-甲基-N-对甲苯磺酰吲哚，产率达85%。
• Experimental and Computational Studies on Cp*^CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks
  作者：Liping Li、Hui Gao、Ming Sun、Zhi Zhou、Wei Yi

  DOI：10.1021/acs.orglett.0c01823

  日期：2020.7.17

  is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C–H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C–H activation/alkene insertion/β-H elimination/hydrogen-transfer

  本文描述的是一种不寻常的Cp * Cy Rh（III）催化的分子内位点特异性芳基C–H环化反应，一种高度化学选择性的实验方案，可直接获得具有广泛的底物/官能团耐受性的八元sultams / lactams。实验和计算研究表明，这种转化涉及独特的PivOH辅助的芳基CH活化/烯烃插入/β-H消除/氢转移过程，其中Rh（III）-氢化物为活性中间体，并伴随释放H 2作为主要副产物，因此可以实现具有氧化还原中性和高度原子经济特性的发达的Cp * Cy Rh（III）催化。
• Rhodium(III)‐Catalyzed Annulation of 2‐Alkenyl Anilides with Alkynes through C−H Activation: Direct Access to 2‐Substituted Indolines
  作者：Marc Font、Borja Cendón、Andrés Seoane、José Luis Mascareñas、Moisés Gulías

  DOI：10.1002/anie.201802830

  日期：2018.7.2

  A RhIII complex featuring an electron‐deficient η5‐cyclopentadienyl ligand catalyzed an unusual annulation between alkynes and 2‐alkenyl anilides to form synthetically appealing 2‐substituted indolines. Formally, the process can be viewed as an allylic amination with concomitant hydrocarbonation of the alkyne. Mechanistic experiments indicate that this transformation involves an unusual rhodium migration

  负载Rh III复杂设有缺电子η 5 -环戊二烯基配位体催化炔烃和2-烯基苯胺之间的不寻常的环，以形成合成吸引力2-取代的二氢吲哚。从形式上讲，该过程可被视为伴随炔烃的碳氢化反应的烯丙基胺化反应。力学实验表明，这种转变涉及不寻常的铑迁移，并伴有1,5-H位移。
• Cobalt-Catalyzed (3 + 2) Cycloaddition of Cyclopropene-Tethered Alkynes: Versatile Access to Bicyclic Cyclopentadienyl Systems and Their CpM Complexes
  作者：Carlos Lázaro-Milla、Eduardo da Concepción、Israel Fernández、José L. Mascareñas、Fernando López

  DOI：10.1021/acscatal.4c03080

  日期：2024.8.2

  Low-valent cobalt complexes can promote intramolecular (3 + 2) cycloadditions of alkyne-tethered cyclopropenes to provide bicyclic systems containing highly substituted cyclopentadienyl moieties with electronically diverse functional groups. The adducts can be easily transformed into new types of CpRh(III) and CpIr(III) complexes, which show catalytic activity in several relevant transformations. Preliminary

  低价钴配合物可以促进炔系环丙烯的分子内（3 + 2）环加成，以提供含有高度取代的环戊二烯基部分和电子多样化官能团的双环系统。该加合物可以很容易地转化为新型的 CpRh(III) 和 CpIr(III) 配合物，在一些相关的转化中表现出催化活性。初步计算（DFT）和实验研究提供了有关钴催化过程的机械特性的相关信息，并使我们能够合理化其相对于同系铑促进反应的优势。
• Palladium-Catalyzed Formal (5 + 2) Annulation between <i>ortho</i>-Alkenylanilides and Allenes
  作者：Borja Cendón、Noelia Casanova、Cezar Comanescu、Rebeca García-Fandiño、Andrés Seoane、Moisés Gulías、José L. Mascareñas

  DOI：10.1021/acs.orglett.7b00467

  日期：2017.4.7

  2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)(2) and Cu(II) to give highly valuable: 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C-H activation of the alkenylanilide involves a classical concerted metalation-deprotonation (CMD) mechanism.