4-[2-(9-ethyl-3-carbazolyl)-1,3-dithian-2-yl]tetrahydrofuran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-[2-(9-ethyl-3-carbazolyl)-1,3-dithian-2-yl]tetrahydrofuran-2-one
• 英文别名: 4-[2-(9-Ethylcarbazol-3-yl)-1,3-dithian-2-yl]tetrahydrofuran-2-one；4-[2-(9-ethylcarbazol-3-yl)-1,3-dithian-2-yl]oxolan-2-one
• 化学式: C₂₂H₂₃NO₂S₂
• 分子量: 397.562
• InChiKey: NPPAGVPDFHHKPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2(5H)-呋喃酮 、 3,4,5-三甲氧基苯甲醛 、 2-(9-ethyl-3-carbazolyl)-1,3-dithiane 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.75h， 以25%的产率得到(+/-)-(3R,4S)-4-[2-(9-ethyl-3-carbazolyl)-1,3-dithian-2-yl]-3-[1S-(3,4,5-trimethoxyphenyl)hydroxymethyl]tetrahydrofuran-2-one
  参考文献：
  名称：

  Synthesis and cytotoxic activities of analogues of thuriferic acid

  摘要：

  Several analogues of thuriferic acid and derivatives, with the 3,4-methylenedioxyphenyl ring replaced by naphthalene, furan, thiophene and carbazole ring systems, have been prepared. The synthetic strategy is based on a conjugate addition alkylation methodology followed by cationic cyclization in order to obtain the isopodophyllone analogues, which are transformed in the thuriferic acids. Their cytotoxic activities against several tumour cells lines are also described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00280-2

文献信息

• Synthesis and cytotoxic activities of analogues of thuriferic acid
  作者：Blanca Madrigal、Pilar Puebla、Angel Ramos、Rafael Peláez、Dolores Grávalos、Esther Caballero、Manuel Medarde

  DOI：10.1016/s0968-0896(01)00280-2

  日期：2002.2

  Several analogues of thuriferic acid and derivatives, with the 3,4-methylenedioxyphenyl ring replaced by naphthalene, furan, thiophene and carbazole ring systems, have been prepared. The synthetic strategy is based on a conjugate addition alkylation methodology followed by cationic cyclization in order to obtain the isopodophyllone analogues, which are transformed in the thuriferic acids. Their cytotoxic activities against several tumour cells lines are also described. (C) 2001 Elsevier Science Ltd. All rights reserved.