(3aR,4S,7aR)-4-羟基-3,3a,4,7a-四氢呋喃并[5,4-b]吡喃-2-酮 | 73343-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 中文名称: (3aR,4S,7aR)-4-羟基-3,3a,4,7a-四氢呋喃并[5,4-b]吡喃-2-酮
• 英文名称: oxysporone
• 英文别名: 4H-Furo(2,3-b)pyran-2(3H)-one, 3a,7a-dihydro-4-hydroxy-, (3aR,4S,7aR)-rel-；(3aR,4S,7aR)-4-hydroxy-3,3a,4,7a-tetrahydrofuro[2,3-b]pyran-2-one
• CAS: 73343-08-5
• 化学式: C₇H₈O₄
• 分子量: 156.138
• InChiKey: RJIMODGWTUNSPV-JCGDXUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,4S,7aR)-4-羟基-3,3a,4,7a-四氢呋喃并[5,4-b]吡喃-2-酮 在 Jones reagent 、 氢气 、 铂 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 4.17h， 生成 2-(2,3-二氢-4-吡喃基)乙酸
  参考文献：
  名称：

  Bioactivity studies of oxysporone and several derivatives

  摘要：

  Recently oxysporone, a phytotoxic dihydrofuropyranone, was isolated along with two closely related compounds, afritoxinones A and B, from liquid cultures of Diplodia africana, an invasive fungal pathogen of Phoenicean juniper. In this study, eight derivatives were hemisynthesized and assayed for their phytotoxic and antifungal activities in comparison to the parent compound. Each compound was tested on non-host plants and on four destructive plant pathogens such as Athelia rolfsii, Diplodia corticola, Phytophthora cinnamomi and P. plurivora. The results on the phytotoxic activity showed that the dihydrofuropyranone carbon skeleton and both the double bond the hydroxy group of dihydropyran ring appeared to be structural features important in conferring activity. Although the data concerning the antifungal activity did not allow to extract any structure-activity relationships, it should be underlined that the conversion of oxysporone into the corresponding 4-O-benzoyl derivative led to a compound showing a good antifungal activity towards three out of the four organisms tested. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2014.07.005

文献信息

• Bioactivity studies of oxysporone and several derivatives
  作者：Anna Andolfi、Lucia Maddau、Benedetto T. Linaldeddu、Bruno Scanu、Alessio Cimmino、Sara Basso、Antonio Evidente

  DOI：10.1016/j.phytol.2014.07.005

  日期：2014.12

  Recently oxysporone, a phytotoxic dihydrofuropyranone, was isolated along with two closely related compounds, afritoxinones A and B, from liquid cultures of Diplodia africana, an invasive fungal pathogen of Phoenicean juniper. In this study, eight derivatives were hemisynthesized and assayed for their phytotoxic and antifungal activities in comparison to the parent compound. Each compound was tested on non-host plants and on four destructive plant pathogens such as Athelia rolfsii, Diplodia corticola, Phytophthora cinnamomi and P. plurivora. The results on the phytotoxic activity showed that the dihydrofuropyranone carbon skeleton and both the double bond the hydroxy group of dihydropyran ring appeared to be structural features important in conferring activity. Although the data concerning the antifungal activity did not allow to extract any structure-activity relationships, it should be underlined that the conversion of oxysporone into the corresponding 4-O-benzoyl derivative led to a compound showing a good antifungal activity towards three out of the four organisms tested. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.