isomethoxystemofoline | 139768-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isomethoxystemofoline
• 英文别名: methoxystemofoline
• CAS: 139768-07-3
• 化学式: C₂₃H₃₁NO₆
• 分子量: 417.502
• InChiKey: JUBNREDNCJVLEE-VWZUPRTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  66.46
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  1',2'-didehydro-4'-methoxystemofoline 在 氢气 、 palladium dichloride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以43%的产率得到isomethoxystemofoline
  参考文献：
  名称：

  Semisynthesis and Acetylcholinesterase Inhibitory Activity of Stemofoline Alkaloids and Analogues

  摘要：

  Semisynthesis of the known Stemona alkaloids oxystemofoline (7) and methoxystemofoline (8) has been achieved starting from (11Z)-1',2'-didehydrostemofoline (6). which confirmed their structures and absolute configurations. The synthesis of (1'R)-hydroxystemololine (9) helped establish this compound as a natural product from Stemona aphylla. (1'S)-Hydroxystemofoline (10) and a number of related analogues were also prepared. In a TLC bioautographic assay, 9 was found to be the most active acetylcholinesterase inhibitor, but it was not as active as galanthamine.

  DOI：

  10.1021/np100137h

文献信息

• Enantioselective total synthesis of (+)-methoxystemofoline and (+)-isomethoxystemofoline
  作者：Pei-Qiang Huang、Su-Yu Huang、Long-Hui Gao、Zhong-Yi Mao、Zong Chang、Ai-E Wang

  DOI：10.1039/c4cc09598g

  日期：——

  We report the first enantioselective total synthesis of (+)-methoxystemofoline (2) and (+)-isomethoxystemofoline (3). Through this work, the structure of methoxystemofoline was revised as 2 with an 11E-stereochemistry, and its absolute configuration was established.

  我们报告了(+) -methoxystemofoline（2）和(+) -isomethoxystemofoline（3）的第一次对映选择性全合成。通过这项工作，methoxystemofoline的结构被修订为2，具有11E-立体化学结构，并且其绝对构型已确定。