artabolide | 1447513-97-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: artabolide
• 英文别名: (3aS,6E,9R,10S,11aR)-9-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,10,11,11a-octahydrocyclodeca[b]furan-2-one
• CAS: 1447513-97-4
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: NIOOUWHPWMWZNY-VXEGPBOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  artabolide 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以0.6 mg的产率得到artabolide-(S)-MTPA ester
  参考文献：
  名称：

  Artabolide, a novel polar auxin transport inhibitor isolated from Artemisia absinthium

  摘要：

  A new sesquiterpene with an alpha-methylene-gamma-lactone moiety, artabolide (1), and three known derivatives 2-4 were isolated from Artemisia absinthium. The structure of 1 was elucidated by 1D and 2D NMR analyses, and the absolute configuration was determined using the modified Mosher's method and X-ray crystal structural analysis. Approximately 2.5 mu g/plant treatment of artabolide (1) exhibited ca. 50% inhibition of polar auxin transport in radish hypocotyls, while 2-4 showed no significant inhibitory activity. Therefore, these results support the importance of the alpha-methylene-gamma-lactone moiety for the inhibition of polar auxin transport. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.052