(-)-O-dimethyltrachelogenine | 146196-54-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (-)-O-dimethyltrachelogenine
• 英文别名: (3S,4S)-3,4-bis[(3,4-dimethoxyphenyl)methyl]-3-methoxyoxolan-2-one
• CAS: 146196-54-5
• 化学式: C₂₃H₂₈O₇
• 分子量: 416.471
• InChiKey: HJAWREDNNMIVLE-SBUREZEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 去甲络石甙元 以 甲醇 为溶剂， 反应 48.0h， 以6.9 mg的产率得到(-)-O-dimethyltrachelogenine
  参考文献：
  名称：

  Lignanes。16.合成首字母总计为（+）-wikstromol，（-）-trachélogénine，（（-）-nortrachélogénine）和表观密码。

  摘要：

  Racemic and optically active alpha,beta-dibenzyl-gamma-butyrolactones (of synthetic origin) were hydroxylated in the alpha position with respect to the carbonyl group, using oxygen in the presence of LHDS. This led to (-)-trachelogenin 1, (-)-nortrachelogenin 2 and (+)-wikstromol 3, whose interesting pharmacological properties were recently described. These natural lignans were correlated to (+/-)-methyltrachelogenin 12 whose relative structure was definitely established by X-ray cristallography.

  DOI：

  10.1016/s0040-4020(01)89041-4

文献信息

• Lignanes. 16. Premières synthèses totales du (+)-wikstromol, de la (−)-trachélogénine, de la (−)-nortrachélogénine et des lignoïdes apparentés
  作者：Melle Kenza Khamlach、Robert Dhal、Eric Brown

  DOI：10.1016/s0040-4020(01)89041-4

  日期：——

  Racemic and optically active alpha,beta-dibenzyl-gamma-butyrolactones (of synthetic origin) were hydroxylated in the alpha position with respect to the carbonyl group, using oxygen in the presence of LHDS. This led to (-)-trachelogenin 1, (-)-nortrachelogenin 2 and (+)-wikstromol 3, whose interesting pharmacological properties were recently described. These natural lignans were correlated to (+/-)-methyltrachelogenin 12 whose relative structure was definitely established by X-ray cristallography.