(10-(sec-butyl)-6-hydroxy-1,7,9-trimethyl-1,6,7,8,9,9a-hexahydro-1,4-methanobenzo-[d]oxepin-2(4H)-ylidene)acetaldehyde | 1446701-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: (10-(sec-butyl)-6-hydroxy-1,7,9-trimethyl-1,6,7,8,9,9a-hexahydro-1,4-methanobenzo-[d]oxepin-2(4H)-ylidene)acetaldehyde
• 英文别名: coicenal A
• CAS: 1446701-33-2
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: VLVIMVZGQOTSGT-FJVKOCMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (10-(sec-butyl)-6-hydroxy-1,7,9-trimethyl-1,6,7,8,9,9a-hexahydro-1,4-methanobenzo-[d]oxepin-2(4H)-ylidene)acetaldehyde 在 乙酰氯 作用下， 以 氘代氯仿 为溶剂， 反应 24.0h， 生成 (2-(sec-butyl)-5-hydroxy-1,6,8-trimethyl-2,5,6,7,8,8a-hexahydro-1H-4a,1-(epoxymethano)naphthalen-10-ylidene)acetaldehyde
  参考文献：
  名称：

  Coicenals A–D, Four New Diterpenoids with New Chemical Skeletons from the Plant Pathogenic Fungus Bipolaris coicis

  摘要：

  Coicenals A-C (1-3) possessing a previously undescribed 10-(sec-butyl)-6-hydroxy-1,7,9-trimethyl-1,6,7,8,9,9a-hexahydro-1,4-methanobenzo[d]oxepin-2(4H)-ylidene)acetaldehyde skeleton and coicenal D (4) with a new 2-(sec-butyl)-5-hydroxy-1,6,8-trimethyl-2,5,6,7,8,8a-hexahydro-1H-4a,1-(epoxymethano)naphthalen-10-ylidene)acetaldehyde skeleton were isolated from the solid culture of the plant pathogenic fungus Bipolar's colds. The absolute configurations in 1 and 4 were assigned by electronic circular dichroism (ECD) calculations. Compounds 1 and 2 were transformed into 4 and 5 by treatment with acetyl chloride, respectively. Compounds 1-4 showed moderate inhibitory activity against NO release with IC50 values of 16.34 +/- 1.12, 23.55 +/- 1.37, 10.82 +/- 0.83, and 54.20 +/- 2.82 mu M, respectively.

  DOI：

  10.1021/ol401736z