(E)-1-(Phenylsulfonyl)-3-(β-methoxyvinyl)indole | 110128-40-0

• 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: (E)-1-(Phenylsulfonyl)-3-(β-methoxyvinyl)indole
• 英文别名: 1-phenylsulfonyl-(E)-β-methoxy-3-vinylindole；(E)-1-(Phenylsulfonyl-indol-3-yl)-2-methoxy-ethen；E-N-Benzolsulfonyl-3(2-methoxyvinyl)-indol；1-(benzenesulfonyl)-3-[(E)-2-methoxyethenyl]indole
• CAS: 110128-40-0
• 化学式: C₁₇H₁₅NO₃S
• 分子量: 313.377
• InChiKey: ZNAKLKROZCSJNM-VAWYXSNFSA-N

物化性质

• 熔点：
  196-197 °C
• 沸点：
  524.2±42.0 °C(Predicted)
• 密度：
  1.21±0.1 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：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(Phenylsulfonyl)-3-(β-methoxyvinyl)indole 在 氧气 、 tetraphenylporphyrin 作用下， 反应 0.67h， 以98%的产率得到cis-9,9a-Dihydro-3-methoxy-9-(phenylsulfonyl)-3H-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：

  1-(苯磺酰)-3-吲哚甲醛 、 (methoxymethyl)triphenylphosphonium chloride 以60%的产率得到
  参考文献：
  名称：

  RINDOR, ULF;PFEUFFER, LUDWIG, HETEROCYCLES, 26,(1987) N 2, 325-327

  摘要：

  DOI：

文献信息

• 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
• Efficient one-pot synthesis of anti HIV and antitumor compounds: harman and substituted harmans
  作者：Radhika S. Kusurkar、Shailesh K. Goswami、Sandhya M. Vyas

  DOI：10.1016/s0040-4039(03)01046-3

  日期：2003.6

  Anti HIV and antitumor compounds, harman and substituted harmans have been synthesized using electrocyclization reactions as key steps. A one-pot reaction sequence was used to furnish these compounds in good overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Efficient one-pot synthesis of anti-HIV and anti-tumour β-carbolines
  作者：Radhika S Kusurkar、Shailesh K Goswami

  DOI：10.1016/j.tet.2004.04.079

  日期：2004.6

  Thermal electrocyclisation of the azahexatriene system has been used as a key step for the synthesis of anti-HIV and anti-tumour compounds, harman, derivatives of harman and 1-aryl-beta-carbolines. A one-pot reaction sequence was used to furnish these compounds in good yield. (C) 2004 Elsevier Ltd. All rights reserved.
• New Diels-Alder Reactions of Oxy-functionalized 3-Vinylindoles with Carbodienophiles
  作者：Ulf Pindur、Martina Rogge

  DOI：10.3987/com-95-7235

  日期：——

  Some new Diels-Alder reactions of oxy-functionalized 3-vinylindoles (1, 2) with carbodienophiles are described. In most cases, functionalized carbazoles (4 - 6, 10 and 11) were formed regio- and/or endo-selectively, The product spectrum is characterized by [4 + 2] cycloadditions, elimination and ene reaction.
• New Diels-Alder reactions of (E/Z)-2'-methoxy-substituted 3-vinylindoles with carbo- and heterodienophiles: regio- and stereoselective access to [b]-annelated indoles and functionalized or [a]-annelated carbazoles
  作者：Ulf Pindur、Myung Hwa Kim、Martina Rogge、Werner Massa、Michel Molinier

  DOI：10.1021/jo00029a023

  日期：1992.1

  The (E/Z)-2'-methoxy-substituted 3-vinylindoles 1a,b react with some carbo- and azodienophiles to furnish new carbazoles and pyridazinoindoles. The conservation of the E and Z stereochemistry of 1 in these Diels-Alder reactions was investigated, and a mechanistic rationalization is given for the stereoselective and regioselective results observed.