Heliannuol D

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: Heliannuol D
• 英文别名: (2S,5S)-2-(2-Hydroxypropan-2-yl)-5,8-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-7-ol
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: BIIJJHXLFCDTIZ-XPTSAGLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-((2S,5S)-7-Methoxymethoxy-5,8-dimethyl-2,3,4,5-tetrahydro-benzo[b]oxepin-2-yl)-propan-2-ol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到Heliannuol D
  参考文献：
  名称：

  Enantioselective total synthesis of heliannuols D and A †

  摘要：

  Heliannuols D和A表现出拮抗作用，首次通过碱介导的分子内环化合成，它们是通过苯酚环氧化物的手性选择性合成的，绝对结构通过全合成确立。

  DOI：

  10.1039/b003553j

文献信息

• Structural Elucidation and Chemistry of a Novel Family of Bioactive Sesquiterpenes: Heliannuols
  作者：Francisco A. Macias、Jose M. G. Molinillo、Rosa M. Varela、Ascension Torres、Frank R. Fronczek

  DOI：10.1021/jo00105a052

  日期：1994.12

  From the moderately polar active fractions of leaf aqueous extract of Helianthus annuus L. var. SH-222 and VYP, we have isolated three new sesquiterpenes which contain a previously unknown skeleton, heliannuols B-D (2-4). The structural elucidation of heliannuols was based on extensive spectral studies, including H-1-H-1 COSY, H-1-C-13 HETCOR, and NOE difference experiments, X-ray diffraction analysis of 4, and chemical correlation between 1, 2, and 4. A biosynthetic pathway that involves an oxirane ring opening is proposed for heliannuols A (1) and D (4), while a phenonium ion intermediate is proposed for heliannuol C (3). The oxirane ring opening and the formation of this intermediate have been evaluated using the semiempirical method PM3. Allelopathic activity bioassays of compound 1-4 suggest that those members of a new class of bioactive sesquiterpenes may be involved in the cultivar sunflower defense against dicotyledon species.