Oxostephamiersin | 52466-83-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈苏巴南生物碱
• 英文名称: Oxostephamiersin
• 英文别名: Oxostephamiersine；(1R,8S,10S,11R,12R)-3,4,11,12-tetramethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.18,11.01,10.02,7]octadeca-2(7),3,5-triene-13,16-dione
• CAS: 52466-83-8
• 化学式: C₂₁H₂₅NO₇
• 分子量: 403.432
• InChiKey: UMLCCHVXIGOAFZ-NAHVHIFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Oxostephamiersin 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 生成 Dihydrooxostephamiersin
  参考文献：
  名称：

  Constitution of four new hasubanan alkaloids from Stephania japonica miers.

  摘要：

  Four new hasubanan alkaloids, stephamiersine (1), epistephamiersine (2), oxostephamiersine (3) and stephasunoline (4) were isolated together with seven known and three unidentified alkaloids from Stephania japonica MIERS (Menispermaceae). Among these new alkaloids, 1 and 2 were found to be epimeric isomers with respect to the C-7 methoxyl group. Permanganate oxidation of 1 gave 3, and borohydride reduction of 1 and 2 gave the highly stereoselective products, dihydrostephamiersine (6) and dihydroepistephamiersine (5). On mild treatment of 5 with hydrochloric acid gave 4. Acetolyses of 1, 2, 5 and 6 gave the phenanthrene derivatives, 7, 8 and 9, respectively. Further, both 1 and 2 were converted to the conjugated carbonyl compound (14) which was obtained from dihydro-16-oxohasubanonine (17a) (17b). On the other hand, the stereochemistry of 1, 2, 3 and 4 was elucidated by nuclear magnetic resonance (NMR) spectroscopic studies as follows : the C-7 methoxyl group of 1 has the α-axial and that of 2 and 4 has the β-equatorial configuration, and the hydroxyl group of 4 has the β-axial one. On the basis of the above chemical correlation coupled with the spectral arguments, the constitution of the new alkaloids was represented as drawn in the formulas, 1, 2, 3 and 4.

  DOI：

  10.1248/cpb.23.1323
• 作为产物：
  描述：

  Stephamiersin 在 potassium permanganate 、 magnesium sulfate 作用下， 以 丙酮 为溶剂， 生成 Oxostephamiersin
  参考文献：
  名称：

  Constitution of four new hasubanan alkaloids from Stephania japonica miers.

  摘要：

  Four new hasubanan alkaloids, stephamiersine (1), epistephamiersine (2), oxostephamiersine (3) and stephasunoline (4) were isolated together with seven known and three unidentified alkaloids from Stephania japonica MIERS (Menispermaceae). Among these new alkaloids, 1 and 2 were found to be epimeric isomers with respect to the C-7 methoxyl group. Permanganate oxidation of 1 gave 3, and borohydride reduction of 1 and 2 gave the highly stereoselective products, dihydrostephamiersine (6) and dihydroepistephamiersine (5). On mild treatment of 5 with hydrochloric acid gave 4. Acetolyses of 1, 2, 5 and 6 gave the phenanthrene derivatives, 7, 8 and 9, respectively. Further, both 1 and 2 were converted to the conjugated carbonyl compound (14) which was obtained from dihydro-16-oxohasubanonine (17a) (17b). On the other hand, the stereochemistry of 1, 2, 3 and 4 was elucidated by nuclear magnetic resonance (NMR) spectroscopic studies as follows : the C-7 methoxyl group of 1 has the α-axial and that of 2 and 4 has the β-equatorial configuration, and the hydroxyl group of 4 has the β-axial one. On the basis of the above chemical correlation coupled with the spectral arguments, the constitution of the new alkaloids was represented as drawn in the formulas, 1, 2, 3 and 4.

  DOI：

  10.1248/cpb.23.1323