3-methyl-N-p-nitrobenzenesulfonylindole | 697742-45-3

• 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-methyl-N-p-nitrobenzenesulfonylindole
• 英文别名: 3-methyl-1-((4-nitrophenyl)sulfonyl)-1H-indole；3-Methyl-1-(4-nitrobenzene-1-sulfonyl)-1H-indole；3-methyl-1-(4-nitrophenyl)sulfonylindole
• CAS: 697742-45-3
• 化学式: C₁₅H₁₂N₂O₄S
• 分子量: 316.337
• InChiKey: KUJHAQXRRKRAHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  93.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-N-p-nitrobenzenesulfonylindole 在 镍 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以59%的产率得到1-(4-aminobenzenesulfonyl)-3-methylindole
  参考文献：
  名称：

  N1-Benzenesulfonylgramine and N1-benzenesulfonylskatole: novel 5-HT6 receptor ligand templates

  摘要：

  1-Benzenesulfonyl-5-methoxy-N,N-dimethyltryptamine (3; K-i=2.3 nM) is a 5-HT6 receptor antagonist: removal of the 5-methoxy group (i.e., 6; K-i = 4.1 nM) has little impact on receptor affinity. In the present study, it is shown that the aminomethyl portion of 6 can be shortened to gramine analogue 10a (K-i = 3.1 nM) a related skatole derivative 11b (K-i = 12 nM) also binds with high affinity indicating that the aminoethyl portion of the tryptamines is not required Cor binding. Compounds 10a and 11b represent members of novel classes of 5-HT6 antagonists. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00612-7
• 作为产物：
  描述：

  1-硝基-2-丙-1-烯-2-基苯 在 sodium thiosulfate 、 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 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

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%。
• 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.
• Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinyl­anilines with O2 as Terminal Oxidant and TEMPO as Cocatalyst
  作者：Sherry Chemler、Timothy Liwosz

  DOI：10.1055/s-0034-1379015

  日期：——

  A copper-catalyzed intramolecular alkene oxidative amination that utilizes TEMPO as co-catalyst and O₂ as the terminal oxidant has been developed. The method furnishes N-aryl and N-sulfonyl indoles from N-aryl and N-sulfonyl 2-vinylanilines, respectively. Additionally, sequential copper-catalyzed reactions where initial Chan-Lam coupling of 2-vinylanilines with arylboronic acids is followed by oxidative amination of the alkene can generate N-aryl indoles in one pot.
• Novel formation of indoles and 3,1-benzoxazines from o-alkenylanilides and dimethyl(methylthio)sulfonium trifluoromethanesulfonate
  作者：Kentaro Okuma、Takumi Yasuda、Itsuki Takeshita、Kosei Shioji、Yoshinobu Yokomori

  DOI：10.1016/j.tet.2007.05.111

  日期：2007.8

  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.
• N1-Benzenesulfonylgramine and N1-benzenesulfonylskatole: novel 5-HT6 receptor ligand templates
  作者：Manik R. Pullagurla、Małgorzata Dukat、Vincent Setola、Bryan Roth、Richard A. Glennon

  DOI：10.1016/s0960-894x(03)00612-7

  日期：2003.10

  1-Benzenesulfonyl-5-methoxy-N,N-dimethyltryptamine (3; K-i=2.3 nM) is a 5-HT6 receptor antagonist: removal of the 5-methoxy group (i.e., 6; K-i = 4.1 nM) has little impact on receptor affinity. In the present study, it is shown that the aminomethyl portion of 6 can be shortened to gramine analogue 10a (K-i = 3.1 nM) a related skatole derivative 11b (K-i = 12 nM) also binds with high affinity indicating that the aminoethyl portion of the tryptamines is not required Cor binding. Compounds 10a and 11b represent members of novel classes of 5-HT6 antagonists. (C) 2003 Elsevier Ltd. All rights reserved.