decumbic acid | 390401-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: decumbic acid
• 英文别名: (2R)-4-Methyl-5-oxo-2-propyl-2,5-dihydrofuran-3-carboxylic acid；(2R)-4-methyl-5-oxo-2-propyl-2H-furan-3-carboxylic acid
• CAS: 390401-25-9
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: GMDXRLRSQUTZAT-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  MB-3 在 乙酸酐 作用下， 反应 1.0h， 以29%的产率得到decumbic acid
  参考文献：
  名称：

  Isolation of an α-methylene-γ-butyrolactone derivative, a toxin from the plant pathogen Lasiodiplodia theobromae

  摘要：

  Lasiodiplodia theobromae is known as a multi-infectious microorganism that causes considerable crop damage, particularly to tropical fruits. When the fruits are infected by L. theobromae, the typical symptom is the appearance of black spots on the surface of the infected fruit. When injected in to the peel of banana, the culture filtrate of L. theobromae induced formation of black spots. The structure of the isolated compound responsible for this effect was determined to be (3S,4R)-3-carboxy-2-methylene-heptan-4-olide on the basis of analysis of MS, IR, and H-1 and C-13 NMR spectroscopic data, including HMQC, HMBC, and H-1-H-1 COSY experiments. The active compound was not only isolated from the culture filtrate derived from potato dextrose medium, but also from the extract of infected peels of bananas. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2004.08.011

文献信息

• Five new lactone derivatives from the stems of Dendrobium nobile
  作者：Xue-Ming Zhou、Cai-Juan Zheng、Jia-Ting Wu、Guang-Ying Chen、Jun Chen、Chong-Ge Sun

  DOI：10.1016/j.fitote.2016.10.002

  日期：2016.12

  Five new lactone derivatives decumbic acids A and B (1 and 2), (-)-decumbic acid (3a), (-)- and (+)-dendrolactone (4a and 4b) together with four known compounds (3b and 5-7) were isolated from the stems of Dendrobium nobile. Their structures were elucidated using comprehensive spectroscopic methods. Compounds 3a and 3b, 4a and 4b were isolated as two pair of enantiomers by chiral HPLC. The absolute

  五个新的内酯衍生物癸二酸A和B（1和2），（-）-癸二酸（3a），（-）-和（+）-树烯内酯（4a和4b）以及四个已知化合物（3b和5- 7）从石D的茎中分离出来。使用全面的光谱方法阐明了它们的结构。通过手性HPLC分离为两对对映异构体的化合物3a和3b，4a和4b。通过旋光和X射线晶体学分析确定1、2、3a，4a和4b的绝对构型。评价了所有化合物对九种植物病原性真菌和三种癌细胞系的抑制活性。
• Isolation of an α-methylene-γ-butyrolactone derivative, a toxin from the plant pathogen Lasiodiplodia theobromae
  作者：Guochun He、Hideyuki Matsuura、Teruhiko Yoshihara

  DOI：10.1016/j.phytochem.2004.08.011

  日期：2004.10

  Lasiodiplodia theobromae is known as a multi-infectious microorganism that causes considerable crop damage, particularly to tropical fruits. When the fruits are infected by L. theobromae, the typical symptom is the appearance of black spots on the surface of the infected fruit. When injected in to the peel of banana, the culture filtrate of L. theobromae induced formation of black spots. The structure of the isolated compound responsible for this effect was determined to be (3S,4R)-3-carboxy-2-methylene-heptan-4-olide on the basis of analysis of MS, IR, and H-1 and C-13 NMR spectroscopic data, including HMQC, HMBC, and H-1-H-1 COSY experiments. The active compound was not only isolated from the culture filtrate derived from potato dextrose medium, but also from the extract of infected peels of bananas. (C) 2004 Elsevier Ltd. All rights reserved.