1-(Phenylsulfonyl)-3-(2-propenyl)-indol | 117760-49-3

• 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: 1-(Phenylsulfonyl)-3-(2-propenyl)-indol
• 英文别名: 1-(Phenylsulfonyl)-3-(2-propenyl)indole；3-isopropenyl-1-phenylsulfonyl-1H-indole；3-(1-methylvinyl)-1-(phenylsulfonyl)indole；3-(1-methylethenyl)-1-phenylsulfonyl-1H-indole；1-(Benzenesulfonyl)-3-prop-1-en-2-ylindole
• CAS: 117760-49-3
• 化学式: C₁₇H₁₅NO₂S
• 分子量: 297.378
• InChiKey: UBKYCQVXCZZHQI-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  487.2±38.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(Phenylsulfonyl)-3-(2-propenyl)-indol 在 正丁基锂 、 tetraphenylporphyrine 、 氧气 、 亚甲兰 作用下， 以 四氢呋喃 、 氘代氯仿 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 18.83h， 生成 9-(benzenesulfonyl)-4-[hydroperoxy(methoxy)methyl]-3,9a-dihydro-[1,2]dioxino[3,4-b]indole
  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：

  methyl triphenylphosphonium bromide 、 1-[1-(苯磺酰基)-1H-吲哚-3-基]乙酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以40%的产率得到1-(Phenylsulfonyl)-3-(2-propenyl)-indol
  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

文献信息

• Synthesis of vinylindoles and vinylpyrroles by the Peterson olefination or by use of the Nysted reagent
  作者：Wayland E. Noland、Christopher L. Etienne、Nicholas P. Lanzatella

  DOI：10.1002/jhet.313

  日期：2011.3

  Vinylindoles and vinylpyrroles were prepared from their corresponding aldehydes or ketones using the Peterson olefination, or by use of the Nysted reagent, a commercially available gem‐dimetallic compound. The two methods provide efficient and convenient access to these useful heterocyclic 1,3‐diene systems. J. Heterocyclic Chem., (2011).

  乙烯基吲哚和乙烯基吡咯是使用Peterson烯烃或相应的市售宝石-双金属化合物Nysted试剂，由其相应的醛或酮制得的。两种方法可有效便捷地访问这些有用的杂环1,3-二烯系统。J.杂环化​​学。（2011）。
• New Reactions of 3-Vinyl- and 3-(2-Propenyl)Indoles withN-Phenylmaleimide: [4 + 2] Cycloaddition, ene reaction, and dimerization
  作者：Ludwig Pfeuffer、Ulf Pindur

  DOI：10.1002/hlca.19880710220

  日期：1988.3.16

  aminobutadiene subunit in the selected 3-vinylindoles 1, 3, 6, and 9, stereospecific [4 + 2] cycloadditions (‘endo’-preference) and dimerizations take place on reaction with N-phenylmaleimide. In the reaction of 9 with N-phenylmaleimide in the absence of a Lewis-acid catalyst, a competing ene reaction occurs in addition to the Diels-Alder reaction.

  取决于氨基丁二烯亚基的在所选择的3-vinylindoles取代模式1，3，6，和9，立体特异性[4 + 2]环加成（“内” -preference）和dimerizations采取与反应地方Ñ苯基马来。在不存在路易斯酸催化剂的情况下9与N-苯基马来酰亚胺的反应中，除了狄尔斯-阿尔德反应之外，还发生竞争性烯反应。
• New Diels–Alder reactions of 3-vinylindoles with an aryne: selective access to functionalized [a]anellated carbazoles
  作者：Eugenia Gonzalez、Ulf Pindur、Dieter Schollmeyer

  DOI：10.1039/p19960001767

  日期：——

  for the reactions of donor- and acceptor-substituted 3-vinylindoles with aryne and structurally related 3,4-pyridyne are described. Aryne reacts in Diels–Alder reactions as a dienophile to give rise to a variety of [a]anellated carbazoles in a one-step procedure. Additionally, aryne is involved in an ene or conjugate addition reaction with the initially formed [4 + 2]cycloadduct. Reaction of methyl

  描述了供体和受体取代的3-乙烯基吲哚与亚芳基和与结构相关的3,4-吡啶炔的反应的新结果。Aryne以亲二烯体的形式在Diels-Alder反应中进行反应，从而一步一步产生各种[ a ]芳基咔唑。此外，芳烃与最初形成的[4 + 2]环加合物参与烯或共轭加成反应。（E）-3-（N-甲基吲哚-3-基）丙烯酸甲酯（6）在空气中的反应除预期的Diels-Alder产物外，还提供了新的苯并氧杂环丁烷[ b ]吲哚衍生物14。原位3-乙烯基吲哚 生成的3,4-吡啶炔难以控制，无法分离出具有所需纯度的环加合物。
• Cycloadditions of vinylindoles with chiral carbodienophiles: the first asymmetric Diels-Alder reactions in the vinylhetarane series
  作者：Ulf Pindur、Gundula Lutz、Gudrun Fischer、Dieter Schollmeyer、Werner Massa、Ludger Schröder

  DOI：10.1016/s0040-4020(01)80385-9

  日期：1993.4

  The first asymmetric Diels-Alder reactions of some 3- and 2-vinylindoles with (N-propenoyl)bomane-10,2-sultam are described. With one exception, the experimental results are indicative of a high pi-facial diastereoselectivity. Following a related procedure, 3-vinylindoles were also allowed to react with a racemic bis(naphthylsulfonyl)-dienophile to furnish tetrahydrocarbazoles with endo-diastereoselectivity.
• 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