(2S,3S,Z)-2-(3,5-dimethoxyphenyl)-4-(4-methoxybenzylidene)tetrahydrofuran-3-carboxylic acid | 1224640-45-2

• 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: (2S,3S,Z)-2-(3,5-dimethoxyphenyl)-4-(4-methoxybenzylidene)tetrahydrofuran-3-carboxylic acid
• 英文别名: (2S,3S,4Z)-2-(3,5-dimethoxyphenyl)-4-[(4-methoxyphenyl)methylidene]oxolane-3-carboxylic acid
• CAS: 1224640-45-2
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: SUVKPLCUUSSDHW-WFBUVSJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,Z)-2-(3,5-dimethoxyphenyl)-4-(4-methoxybenzylidene)tetrahydrofuran-3-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以81%的产率得到[(2S,3R,4Z)-2-(3,5-dimethoxyphenyl)-4-[(4-methoxyphenyl)methylidene]oxolan-3-yl]methanol
  参考文献：
  名称：

  Synthesis, chiral resolution, and determination of novel furan lignan derivatives with potent anti-tumor activity

  摘要：

  A kind of racemic furan lignans were synthesized via a novel route, and two optical isomers were obtained through a selective hydrolization. The absolute configurations were determined by circular dichroism spectroscopy after separated through a preparative column. The different activities of isomers and the racemates were evaluated on QGY-7701 and HeLa cell lines, and compound 2c showed the best activity on QGY-7701 and HeLa cell lines with IC50 12 mu M and 13 mu M, respectively. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.122
• 作为产物：
  描述：

  在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 (2S,3S,Z)-2-(3,5-dimethoxyphenyl)-4-(4-methoxybenzylidene)tetrahydrofuran-3-carboxylic acid 、 (2R,3R,Z)-2-(3,5-dimethoxyphenyl)-4-(4-methoxybenzylidene)tetrahydrofuran-3-carboxylic acid
  参考文献：
  名称：

  Synthesis, chiral resolution, and determination of novel furan lignan derivatives with potent anti-tumor activity

  摘要：

  A kind of racemic furan lignans were synthesized via a novel route, and two optical isomers were obtained through a selective hydrolization. The absolute configurations were determined by circular dichroism spectroscopy after separated through a preparative column. The different activities of isomers and the racemates were evaluated on QGY-7701 and HeLa cell lines, and compound 2c showed the best activity on QGY-7701 and HeLa cell lines with IC50 12 mu M and 13 mu M, respectively. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.122

文献信息

• Synthesis, chiral resolution, and determination of novel furan lignan derivatives with potent anti-tumor activity
  作者：Hai Ling Sun、Tian Tian Wang、Zhi Liang Lv、Ji Lu Feng、Dong Ping Geng、Yong Mei Li、Ke Li

  DOI：10.1016/j.bmcl.2010.01.122

  日期：2010.3

  A kind of racemic furan lignans were synthesized via a novel route, and two optical isomers were obtained through a selective hydrolization. The absolute configurations were determined by circular dichroism spectroscopy after separated through a preparative column. The different activities of isomers and the racemates were evaluated on QGY-7701 and HeLa cell lines, and compound 2c showed the best activity on QGY-7701 and HeLa cell lines with IC50 12 mu M and 13 mu M, respectively. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.