4-(phenylsulfonyl)-4H-furo<3,4-b>indole | 89241-37-2

• 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: 4-(phenylsulfonyl)-4H-furo<3,4-b>indole
• 英文别名: 4-(phenylsulfonyl)-4H-furo[3,4-b]indole；furo<3,4-b>indole；furo[3,4-b]indole；4H-Furo[3,4-b]indole, 4-(phenylsulfonyl)-；4-(benzenesulfonyl)furo[3,4-b]indole
• CAS: 89241-37-2
• 化学式: C₁₆H₁₁NO₃S
• 分子量: 297.334
• InChiKey: YQFHJTLYOSFRPY-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  512.6±42.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  邻溴氟苯 、 4-(phenylsulfonyl)-4H-furo<3,4-b>indole 在 magnesium 作用下， 以38%的产率得到5-(phenylsulfonyl)-6,11-epoxy-6,11-dihydro-5H-benzocarbazole
  参考文献：
  名称：

  4-（苯磺酰基）-4H-呋喃[3,4-b]吲哚-吲哚-2,3-喹二甲烷的稳定合成类似物

  摘要：

  由吲哚-3-羧甲醛（）以28％的收率合成先前未知的稠合杂环4H-呋喃[3,4-b]吲哚的N-苯基磺酰基衍生物（），并与苯炔进行狄尔斯-阿尔德反应，得到5H脱氧和脱保护后，-苯并[b]咔唑（）的收率为33％。

  DOI：

  10.1016/s0040-4039(00)94105-4
• 作为产物：
  描述：

  1-(phenylsulfonyl)-3-formaldehyde ethylene glycol acetal 在 三氟化硼乙醚 、 仲丁基锂 、 对苯二酚 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 6.25h， 生成 4-(phenylsulfonyl)-4H-furo<3,4-b>indole
  参考文献：
  名称：

  An Efficient Synthesis of 4-(Phenylsulfonyl)-4H-furo[3,4-b]indoles

  摘要：

  The fused heterocycle 4-(phenylsulfonyl)-4H-furo-[3,4-b]indole, which is an indole-2,3-quinodimethane synthetic analogue, is prepared in five steps from indole in 46% yield. A similar sequence is used to synthesize C-3 derivatives (3-methyl, 3-phenyl, and 3-heptyl). Thus, indole-3-carbaldehyde (1) is protected as the N-phenylsulfonyl derivative 2 and converted to the ethylene acetal 6. Lithiation at C-2 followed by treatment with an aldehyde affords the expected hydroxy acetals 7 and S. Exposure to acid effects cyclization to the furoindoles 5 and 9. Furthermore, C-1 lithiation of furo[3,4-b]indole 9c followed by treatment with methyl iodide affords disubstituted furo[3,4-b]indole 10.

  DOI：

  10.1021/jo010938q

文献信息

• 4-(phenylsulfonyl)-4H-furo[3,4-b]indole - A stable synthetic analogue of indole-2,3-quinodimethane
  作者：Mark G. Saulnier、Gordon W. Gribble

  DOI：10.1016/s0040-4039(00)94105-4

  日期：1983.1

  The N-phenylsulfonyl derivative () of the previously unknown fused heterocycle 4H-furo[3,4-b]indole is synthesized from indole-3-carboxaldehyde () in 28% yield and undergoes a Diels-Alder reaction with benzyne to give 5H-benzo[b]carbazole () in 33% yield after deoxygenation and deprotection.

  由吲哚-3-羧甲醛（）以28％的收率合成先前未知的稠合杂环4H-呋喃[3,4-b]吲哚的N-苯基磺酰基衍生物（），并与苯炔进行狄尔斯-阿尔德反应，得到5H脱氧和脱保护后，-苯并[b]咔唑（）的收率为33％。
• Syntheses and Diels-Alder cycloaddition reactions of 4H-furo[3,4-b]indoles. A regiospecific Diels-Alder synthesis of ellipticine
  作者：Gordon W. Gribble、Daniel J. Keavy、Deborah A. Davis、Mark G. Saulnier、Benjamin Pelcman、Timothy C. Barden、Mukund P. Sibi、Erik R. Olson、Joseph J. BelBruno

  DOI：10.1021/jo00048a021

  日期：1992.10

  Seven examples of the novel 4H-furo[3,4-b]indole ring system (3-9)-a stable, synthetic analogue of indole-2,3-quinodimethane-have been synthesized in 6-8 steps from simple indoles in overall yields of 21-28%. These 4H-furo[3,4-b]indoles undergo Diels-Alder reactions with several dienophiles (dimethyl acetylenedicarboxylate, N-phenylmaleimide, benzyne), including ethyl acrylate, which reacts regiospecifically with furoindole 4 to afford a single carbazole ester (59). This result, predicted by molecular orbital calculations, was used to design and execute a regiospecific Diels-Alder synthesis of the antitumor alkaloid ellipticine (63). Thus, the trimethylsilyl triflate-induced reaction between furoindole 4 and dihydropyridone 68b is greater-than-or-equal-to 99% regioselective and affords lactam 70b in 89% yield. Further manipulation gives ellipticine (63) with no detectable (<1%) isoellipticine (64) in the crude product.
• An Efficient Synthesis of 4-(Phenylsulfonyl)-4<i>H</i>-furo[3,4-<i>b</i>]indoles
  作者：Gordon W. Gribble、Jun Jiang、Yanbing Liu

  DOI：10.1021/jo010938q

  日期：2002.2.1

  The fused heterocycle 4-(phenylsulfonyl)-4H-furo-[3,4-b]indole, which is an indole-2,3-quinodimethane synthetic analogue, is prepared in five steps from indole in 46% yield. A similar sequence is used to synthesize C-3 derivatives (3-methyl, 3-phenyl, and 3-heptyl). Thus, indole-3-carbaldehyde (1) is protected as the N-phenylsulfonyl derivative 2 and converted to the ethylene acetal 6. Lithiation at C-2 followed by treatment with an aldehyde affords the expected hydroxy acetals 7 and S. Exposure to acid effects cyclization to the furoindoles 5 and 9. Furthermore, C-1 lithiation of furo[3,4-b]indole 9c followed by treatment with methyl iodide affords disubstituted furo[3,4-b]indole 10.