1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole | 89241-38-3

• 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: 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole
• 英文别名: 4-(phenylsulfonyl)-1,3-dimethyl-4H-furo[3,4-b]indole；4H-Furo[3,4-b]indole, 1,3-dimethyl-4-(phenylsulfonyl)-；4-(benzenesulfonyl)-1,3-dimethylfuro[3,4-b]indole
• CAS: 89241-38-3
• 化学式: C₁₈H₁₅NO₃S
• 分子量: 325.388
• InChiKey: QBCCASYEPMKURP-UHFFFAOYSA-N

物化性质

• 沸点：
  525.0±42.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole 、 丙烯酸乙酯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 以63%的产率得到3-carbethoxy-1,4-dimethyl-9-(phenylsulfonyl)carbazole
  参考文献：
  名称：

  Syntheses and Diels-Alder cycloaddition reactions of 4H-furo[3,4-b]indoles. A regiospecific Diels-Alder synthesis of ellipticine

  摘要：

  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.

  DOI：

  10.1021/jo00048a021
• 作为产物：
  描述：

  吲哚-2-羧酸甲酯 在 manganese(IV) oxide 、 氯化亚砜 、 四甲基乙二胺 、 叔丁基锂 、 sodium hydride 、 溶剂黄146 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole
  参考文献：
  名称：

  A convenient access to 1,3-disubstituted furo[3,4-b]indoles by acid ion-exchange resin-catalyzed furan formation

  摘要：

  Efficient synthesis of furo[3,4-b]indoles starting from the corresponding indole is reported. The first route involves derivatization, protection, and deprotection steps, which stretch the syntheses. The second method provides a shorter and more efficient strategy to accessing the furoindole. The innovation starts with alkylation at C-2 of the indole presenting at the C-3 position a ketone-acetal, followed by the cycloaromatization catalyzed by polymeric ion-exchange resins. The second route represents a significant improvement over other methods previously described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.022

文献信息

• Synthesis of Ellipticine by Hetaryne Cycloadditions − Control of Regioselectivity
  作者：Maite Díaz、Agustín Cobas、Enrique Guitián、Luis Castedo

  DOI：10.1002/1099-0690(200112)2001:23<4543::aid-ejoc4543>3.0.co;2-#

  日期：2001.12

  We have modified Gribble’s and Moody’s approaches to ellipticines by introducing substituents into the 3,4-didehydropyridine dienophile to control the key cycloaddition step. A chloro substituent at position 2 improved the yields and the regioselectivities of the cycloadditions and the overall efficiency of the synthesis of ellipticine.

  我们通过向3,4-didehydropyridined dienophile中引入取代基来控制关键的环加成步骤，从而改进了Gribble和Moody对玫瑰树碱的制备方法。2位的氯取代基提高了环加成的产率和区域选择性以及玫瑰树碱的合成总效率。
• A regioselective diels-alder synthesis of ellipticine
  作者：Deborah A. Davis、Gordon W. Gribble

  DOI：10.1016/s0040-4039(00)88731-6

  日期：——

  4-b]indole (3) and 5,6-dihydropyridones (10) shows high regioselectivity, yielding carbazole 11 upon hydrolytic workup. Carbazole 11b has been successfully converted to the pyridocarbazole alkaloid ellipticine (1).

  1,3-二甲基-4-（苯基磺酰基）-4H-呋喃[3,4-b]吲哚（3）和5,6-二氢吡啶酮（10）之间的三甲基甲硅烷基三氟甲磺酸酯加速Diels-Alder反应显示出较高的区域选择性，从而产生咔唑水解后处理为11。咔唑11b已成功转化为吡啶并咔唑生物碱玫瑰树碱（1）。
• 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％。
• Synthesis and Cytotoxicity of Novel Bis-Ellipticines and Bis-Isoellipticines
  作者：Gordon W. Gribble、Judy A. Obaza-Nutaitis

  DOI：10.3987/com-18-s(f)6

  日期：——
• Synthesis and Diels-Alder reactions of 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole. A new annulation strategy for the construction of ellipticine and isoellipticine
  作者：Gordon W. Gribble、Mark G. Saulnier、Mukund P. Sibi、Judy A. Obaza-Nutaitis

  DOI：10.1021/jo00197a039

  日期：1984.11