maturone | 29100-83-2

• 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: maturone
• 英文别名: Maturon；3-(Hydroxymethyl)-5-methylnaphtho[2,3-b]furan-4,9-dione；3-(hydroxymethyl)-5-methylbenzo[f][1]benzofuran-4,9-dione
• CAS: 29100-83-2
• 化学式: C₁₄H₁₀O₄
• 分子量: 242.231
• InChiKey: KDAMTLGCZPUMAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(2,2-Dimethyl-[1,3]dioxan-5-yl)-5-methyl-naphthalen-2-ol 在 lithium aluminium tetrahydride silver(II) oxide 、 草酰氯 、 硝酸 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 、 乙腈 为溶剂， 反应 1.17h， 生成 maturone
  参考文献：
  名称：

  Synthesis of maturone

  摘要：

  DOI：

  10.1016/s0040-4039(00)83921-0

文献信息

• Furannulation strategy for synthesis of the naturally occurring fused 3-methylfurans: efficient synthesis of evodone and menthofuran and regioselective synthesis of maturone via a Lewis acid catalyzed Diels-Alder reactions. Some comments for its mechanistic aspects
  作者：Mariko Aso、Akio Ojida、Guang Yang、Ok Ja Cha、Eiji Osawa、Ken Kanematsu

  DOI：10.1021/jo00067a031

  日期：1993.7

  Fused 3-methylfurans are readily obtained by the reaction of allenic sulfonium salt 1 and the enolate anions of cyclic 1,3-dicarbonyl compounds in two steps. Using these fused 3-methylfuran compounds as intermediates, furanoterpenoids such as menthofuran (8) and evodone (4b) are synthesized efficiently. Moreover, maturone (15) is also obtained regioselectivity by Lewis acid CatalYzed Diels-Alder reaction of benzofuranquinone (12) with piperylene. In the context with the regioselectivity observed in the Diels-Alder reaction of 12, semiempirical molecular orbital calculations are applied to gain its theoretical interpretation based upon frontier molecular orbital theory and transition state analysis.
• Aso, Mariko; Ojida, Akio; Yang, Guang, Heterocycles, 1993, vol. 35, # 1, p. 33 - 36
  作者：Aso, Mariko、Ojida, Akio、Yang, Guang、Kanematsu, Ken

  DOI：——

  日期：——
• Synthesis of maturone
  作者：E. Ghera、R. Maurya、Y. Ben-David

  DOI：10.1016/s0040-4039(00)83921-0

  日期：1986.1