(+/-) (3R,4S)-4-[2-(5-methyl-2-thienyl)-1,3-dithian-2-yl]-3-[1S-(3,4,5-trimethoxyphenyl)hydroxymethyl]tetrahydrofuran-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-) (3R,4S)-4-[2-(5-methyl-2-thienyl)-1,3-dithian-2-yl]-3-[1S-(3,4,5-trimethoxyphenyl)hydroxymethyl]tetrahydrofuran-2-one
• 英文别名: (3R,4S)-3-[(S)-hydroxy-(3,4,5-trimethoxyphenyl)methyl]-4-[2-(5-methylthiophen-2-yl)-1,3-dithian-2-yl]oxolan-2-one
• 化学式: C₂₃H₂₈O₆S₃
• 分子量: 496.67
• InChiKey: TXSIGUQKQXAPGO-CDHQVMDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  9

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-(1,3-dithian-2-yl)-5-methylthiophene 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 3.75h， 以62%的产率得到(+/-) (3R,4S)-4-[2-(5-methyl-2-thienyl)-1,3-dithian-2-yl]-3-[1R-(3,4,5-trimethoxyphenyl)hydroxymethyl]tetrahydrofuran-2-one
  参考文献：
  名称：

  Heterolignanolides. Furo- and thieno-analogues of podophyllotoxin and thuriferic acid

  摘要：

  The conjugate addition-alkylation to 5H-furan-2-one followed by cyclization and controlled epimerizations have been applied to the synthesis of new furo- and thieno-lignan analogues. Podophyllotoxin and thuriferic acid heteroanalogues have been obtained by this methodology, as representative members of these families. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00271-x

文献信息

• Heterolignanolides. Furo- and thieno-analogues of podophyllotoxin and thuriferic acid
  作者：Angel C Ramos、Rafael Peláez、Jose Luis López、Esther Caballero、Manuel Medarde、Arturo San Feliciano

  DOI：10.1016/s0040-4020(01)00271-x

  日期：2001.4

  The conjugate addition-alkylation to 5H-furan-2-one followed by cyclization and controlled epimerizations have been applied to the synthesis of new furo- and thieno-lignan analogues. Podophyllotoxin and thuriferic acid heteroanalogues have been obtained by this methodology, as representative members of these families. (C) 2001 Elsevier Science Ltd. All rights reserved.