(±)-xylaridine B

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (±)-xylaridine B
• 英文别名: N-[2-methyl-1-oxo-1-(2,5,5,8-tetramethyl-6,9-dioxo-7H-cyclopenta[g]indolizin-8-yl)propan-2-yl]acetamide
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: VWGCVXUECMOABY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-xylaridine B 在 CHIRALPAK AD-H 作用下， 以 环己烷 、 异丙醇 为溶剂， 生成 N-[2-methyl-1-oxo-1-[(8R)-2,5,5,8-tetramethyl-6,9-dioxo-7H-cyclopenta[g]indolizin-8-yl]propan-2-yl]acetamide 、 (+/-)-xylaridine B
  参考文献：
  名称：

  (±)-Xylaridines A and B, Highly Conjugated Alkaloids from the Fungus Xylaria longipes

  摘要：

  Two highly conjugated alkaloids xylaridines A (1) and B (2) were obtained as racemates from the fungus Xylaria longipes. They were resoluted into optically pure enantiomers, respectively. Their structures were determined by extensive spectroscopic analyses, X-ray diffraction, and equivalent circulating density (ECD) calculations. Compound 1 possesses a 5/6/6/5/5 fused ring system with unique 2-azaspiro[4.4]nonane substructure. The hypothesis of biosynthesis pathways for 1 and 2 was proposed.

  DOI：

  10.1021/acs.orglett.9b00312