(+/-)-4-[2-(2-naphthyl)-1,3-dithian-2-yl]tetrahydrofuran-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-4-[2-(2-naphthyl)-1,3-dithian-2-yl]tetrahydrofuran-2-one
• 英文别名: 4-(2-Naphthalen-2-yl-1,3-dithian-2-yl)oxolan-2-one
• 化学式: C₁₈H₁₈O₂S₂
• 分子量: 330.472
• InChiKey: PPBXCFQBXDDZHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  76.9
• 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-(naphthalen-2-yl)-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， 以66%的产率得到(3R,4S)-3-[hydroxy-(3,4,5-trimethoxyphenyl)methyl]-4-(2-naphthalen-2-yl-1,3-dithian-2-yl)oxolan-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

• Naphthalene Analogues of Lignans
  作者：Blanca Madrigal、Pilar Puebla、Rafael Peláez、Esther Caballero、Manuel Medarde

  DOI：10.1021/jo0263364

  日期：2003.2.1

  The methodology for the synthesis of podophyllotoxin and thuriferic acid-type lignans has been applied to derivatives carrying a naphthalene moiety. Starting from the 1,3-dithiane of 2-naphthaldehyde afforded the expected analogues in the 2,1-naphthalene series. The preferred conformations of these compounds are influenced by the bulky naphthalene system. By contrast, 1,8-bridged products were obtained

  鬼臼毒素和苏铁酸型木脂素的合成方法已应用于带有萘部分的衍生物。从2-萘的1，3-二噻吩开始，提供了2，1-萘系列的预期类似物。这些化合物的优选构象受庞大的萘体系影响。相反，从1-萘醛的1，3-二噻吩中获得1，8-桥连产物。在该系列中，脱保护和/或脱硫反应后分离出多环萘木脂素类似物。在该方法中产生的环化是由于3，4，5-三甲氧基苯基部分和1，3-二噻吩环的反应C-2之间的接近性。
• 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.