1-(Phenylsulfonyl)-3-<(β-ethoxycarbonyl)vinyl>indole | 110604-89-2

• 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: 1-(Phenylsulfonyl)-3-<(β-ethoxycarbonyl)vinyl>indole
• 英文别名: ethyl (E)-3-<1-(phenylsulfonyl)indol-3-yl>acrylate；(E)-3-(1-Phenylsulfonyl-indol-3-yl)-propensaeureethylester；(E)-1-phenylsulfonyl-3-(β-carbethoxyvinyl)indole；ethyl (E)-3-[1-(phenylsulfonyl)indol-3-yl]acrylate；ethyl (E)-3-[1-(benzenesulfonyl)indol-3-yl]prop-2-enoate
• CAS: 110604-89-2
• 化学式: C₁₉H₁₇NO₄S
• 分子量: 355.414
• InChiKey: RLQCSDVXGXKQHV-OUKQBFOZSA-N

物化性质

• 沸点：
  559.0±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(Phenylsulfonyl)-3-<(β-ethoxycarbonyl)vinyl>indole 在 氧气 、 tetraphenylporphyrin 作用下， 以 氘代氯仿 为溶剂， 生成 ethyl (3Z)-3-[1-(benzenesulfonyl)-2-hydroxy-2H-indol-3-ylidene]-2-oxopropanoate
  参考文献：
  名称：

  Sensitized photooxygenations of 3-vinylindole derivatives

  摘要：

  A series of 1-methyl- and 1-(phenylsulfonyl)-substituted 3-vinylindoles with different electronic and steric features has been synthesized and their sensitized photooxygenation in aprotic solvents investigated. 1-Methyl-3-vinyl- (1a), 1,2-dimethyl-3-vinyl- (1b), 1-methyl-3-(beta-methoxyvinyl)- (4-Z and 4-E), 1-(phenylsulfonyl)-3-vinyl- (8a), 1-(phenylsulfonyl)-3-(alpha-methylvinyl) (8b), 1-(phenylsulfonyl)-3-(8-methoxyvinyl)- (8c and 8d), and cis-1-(phenylsulfonyl)-3-(alpha-methyl-beta-methoxyvinyl) indoles (15-Z) react with O-1(2) predominantly to give endoperoxides via [4+2] cycloaddition. However, 1,2-dimethyl-3-(beta-methoxyvinyl)indole (1c) gives [2 + 2] cycloaddition with the 3-double bond to give 1,2-dimethyl-3-formylindole (3c); trans-1-(phenylsulfonyl)-3-(alpha-methyl-beta-methoxyvinyl)indole (15-E) gives the 3-indolyl allylic hydroperoxide (17) via ene reaction, along with a small amount of isomerization of the 3-vinyl double bond. A zwitterionic intermediate in the isomerization is proposed. Most of the resulting dioxacarbazole endoperoxides are isolable and inert to reduction by trimethyl phosphite and thiourea except for N-methyldioxacarbazole 5, which undergoes clean rearrangement to indolin-2-one epoxide 7 at -20-degrees-C.

  DOI：

  10.1021/jo00079a032
• 作为产物：
  描述：

  1-(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate 、 丙烯酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以93%的产率得到1-(Phenylsulfonyl)-3-<(β-ethoxycarbonyl)vinyl>indole
  参考文献：
  名称：

  Palladium-Catalyzed Coupling of 3-Indolyl Triflate. Syntheses of 3-Vinyl and 3-Alkynylindoles

  摘要：

  Palladium-catalyzed coupling of 1 -(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate (triflate) (1) with terminal alkenes and alkenes gives 3-vinyl (2) and 3-alkynylindoles in 45-93% yields. An attempt to generate 2,3-indolyne 22 from 2-trimethylsilyl-3-indolyl triflate 20 gives indigo (23).

  DOI：

  10.1080/00397919208019065

文献信息

• Regio- and Stereoselective Synthesis of New Substituted Tetrahydrocarbazoles and Carbazoles Using Diels–Alder Reactions
  作者：Dattatray G. Hingane、Shailesh K. Goswami、Vedavati Puranik、Radhika S. Kusurkar

  DOI：10.1080/00397911.2010.544440

  日期：2012.6.15

  Abstract Diels–Alder reactions of 3-vinylindoles were carried out with methyl acrylate and N-phenylmaleimide as dienophiles under microwave conditions to furnish unreported tetrahydrocarbazoles regio- and stereoselectively in good yields. Further dehydrogenation resulted in new substituted carbazoles. GRAPHICAL ABSTRACT

  摘要 以丙烯酸甲酯和 N-苯基马来酰亚胺作为亲二烯体在微波条件下进行 3-乙烯基吲哚的 Diels-Alder 反应，以区域和立体选择性提供未报道的四氢咔唑，收率良好。进一步脱氢产生新的取代咔唑。图形概要
• Diels-Alder-Reaktionen von 2?-substituierten 3-Vinyl-1H-indolen zu neuen anellierten Indol-und Carbazol-Derivaten
  作者：Ludwig Pfeuffer、Ulf Pindur

  DOI：10.1002/hlca.19870700523

  日期：1987.8.12

  Diels-alder Reactions of 2′-Substituted 3-Vinyl-1H-indoles to New Annellated Indole and Carbazole Derivatives

  2′-取代的3-乙烯基-1 H-吲哚的狄尔斯-阿尔德反应与新的吲哚和咔唑衍生物
• Wittig-Olefinierung zu neuen donor- und akzeptor-substituierten 3-Vinylindolen: Optimierte Syntheseverfahren
  作者：Ulf Pindur、Ludwig Pfeuffer

  DOI：10.1007/bf00808758

  日期：1989.2
• PINDUR, ULF;PFEUFFER, LUDWIG, MONATSH. CHEM., 120,(1989) N, C. 157-162
  作者：PINDUR, ULF、PFEUFFER, LUDWIG

  DOI：——

  日期：——
• ITAHARA, TOSHIO;KAWASAKI, KAZUKUNI;OUSETO, FUMIO, SYNTHESIS, BRD, 1984, N 3, 236-237
  作者：ITAHARA, TOSHIO、KAWASAKI, KAZUKUNI、OUSETO, FUMIO

  DOI：——

  日期：——