3,6-bis(4-hydroxy-3,5-dimethoxyphenyl)tetrahydrofuro[3,4-c]furan-1,4-dione | 65167-29-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 3,6-bis(4-hydroxy-3,5-dimethoxyphenyl)tetrahydrofuro[3,4-c]furan-1,4-dione
• 英文别名: dehydrosinapic acid dilactone；3,6-bis-(4-hydroxy-3,5-dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1,4-dione；3,6-Bis-(4-hydroxy-3,5-dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1,4-dion；(+/-)-2,6-bis(4-hydroxy-3,5-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-4,8-dione；1,4-Bis(4-hydroxy-3,5-dimethoxyphenyl)-1,3a,4,6a-tetrahydrofuro[3,4-c]furan-3,6-dione
• CAS: 65167-29-5
• 化学式: C₂₂H₂₂O₁₀
• 分子量: 446.411
• InChiKey: SOYZXRMXOYGADU-UHFFFAOYSA-N

物化性质

• 沸点：
  726.7±60.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,6-bis(4-hydroxy-3,5-dimethoxyphenyl)tetrahydrofuro[3,4-c]furan-1,4-dione 在 四氢呋喃 、 吡啶 、 lithium aluminium tetrahydride 作用下， 生成 1,4-bis(4-hydroxy-3,5-dimethoxyphenyl)-2,3-bis(hydroxymethyl)-1,4-butanediol
  参考文献：
  名称：

  Freudenberg; Schraube, Chemische Berichte, 1955, vol. 88, p. 16,20

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲氧基-4-羟基肉桂酸 在 甲醇 、 氧气 、 三氯化铁 作用下， 生成 3,6-bis(4-hydroxy-3,5-dimethoxyphenyl)tetrahydrofuro[3,4-c]furan-1,4-dione
  参考文献：
  名称：

  Freudenberg; Schraube, Chemische Berichte, 1955, vol. 88, p. 16,20

  摘要：

  DOI：

文献信息

• Novel tetrahydrofuran structures derived from β–β-coupling reactions involving sinapyl acetate in Kenaf lignins
  作者：Fachuang Lu、John Ralph

  DOI：10.1039/b809464k

  日期：——

  Free radical coupling of sinapyl γ-acetate or cross-coupling between sinapyl acetate and sinapyl alcohol yields novel tetrahydrofuran β–β-(cross-)coupled dehydrodimers. Such substructures are therefore anticipated in naturally acetylated lignins, e.g. in Kenaf, if sinapyl acetate is a component of the lignin monomer pool. The DFRC (derivatization followed by reductive cleavage) method, modified by replacing all acetyl reagents and solvents with their propionyl analogs (DFRC′), allows the analysis of naturally acetylated lignins. DFRC′ treatment of the sinapyl acetate-derived dimers or crossed dimers gave diagnostic products that retain at least one acetate group on a sidechain γ-position; the products have been authenticated by comparison of their mass spectra and GC retention times with those of synthesized compounds. DFRC′ of Kenaf lignins produces the same diagnostic products as from the dimers, implicating the presence of the various tetrahydrofuran units in Kenaf lignins. With data from the model compounds in hand, NMR analysis of Kenaf lignins elegantly confirms the presence of such substructures in the polymer, establishing that acetates on Kenaf lignins arise through incorporation of sinapyl acetate, as a lignin precursor, via enzyme-mediated radical coupling mechanisms.

  自由基耦合愈創木基γ-醋酸酯或愈創木醋酸酯与愈創木醇之间的交叉耦合，可以生成新型的四氢呋喃β-β-(交叉)耦合去氢二聚体。因此，预期在天然醋酸化木质素中会出现这样的亚结构，例如在麻中，如果愈创木醋酸酯是木质素单体池的组成部分。DFRC（衍生化后还原裂解）方法通过用其丙酸酯类似物替代所有醋酸试剂和溶剂（DFRC'）进行改进，使得能够分析天然醋酸化木质素。对由愈创木醋酸酯衍生的二聚体或交叉二聚体进行DFRC'处理得到了诊断产品，这些产品在侧链γ位置至少保留一个醋酸基；通过与合成化合物的质谱和气相色谱保留时间的比较，确认了这些产品。对麻木质素进行DFRC'处理，产生与二聚体相同的诊断产品，表明麻木质素中存在各种四氢呋喃单元。根据模型化合物的数据，NMR分析麻木质素优雅地确认了这些亚结构在聚合物中的存在，证实麻木质素上的醋酸盐是通过作为木质素前体的愈创木醋酸酯，通过酶介导的自由基耦合机制的方式引入的。
• Conversion of phenolics to lignans: Sinapic acid to thomasidioic acid
  作者：M. I. Rubino、S. D. Arntfield、J. L. Charlton

  DOI：10.1007/bf02577839

  日期：1995.12

  Changes in sinapic acid when exposed to aqueous alkaline conditions were elucidated. Sinapic acid was exposed to a volatile buffer (pH 8.5) for 24 h, lyophilized, acidified, extracted, and characterized using nuclear magnetic resonance and mass spectroscopy. The product obtained was identified as the lignan thomasidioic acid. This identification was confirmed by comparison with a synthesized authentic sample of thomasidioic acid. Conversion of sinapic acid to thomasidioic acid under alkaline conditions previously has not been reported. Thomasidioic acid was present after exposure of sinapic acid to pH 8.5 for as few as 6 h. Thomasidioic acid also was formed at pH 7.

  摘要 阐明了山奈酸在水碱性条件下的变化。将山奈酸置于挥发性缓冲液（pH 8.5）中 24 小时，然后冻干、酸化、提取，并利用核磁共振和质谱进行表征。得到的产物被鉴定为木质素 thomasidioic acid。这一鉴定结果通过与合成的真品thomasidioic acid 样品进行比较得到了证实。在碱性条件下将山奈酸转化成托马杉二酸的研究以前从未报道过。山奈酸在 pH 值为 8.5 的环境中暴露 6 小时就会产生托马刁酸，在 pH 值为 7 时也会产生托马刁酸。
• Cerebral-circulation-metabolism-function-improving agent
  申请人：WAKUNAGA SEIYAKU KABUSHIKI KAISHA

  公开号：EP0255287A2

  公开（公告）日：1988-02-03

  Disclosed herein is a cerebral-circulation-­metabolism-function-improving agent which contains a 2,6-­diphenyl-3,7-dioxabicyclo[3.3.0]octane derivative represented by the following formula as the effective ingredient: wherein, each of R₁, R₃, R₄ and R₆ represents a hydrogen atom or a lower alkoxyl group; each of R₂ and R₅ represents a hydrogen atom, a β-D-glucosyl group or a hydroxyl group; and each of R₇ and R₈ represents an oxygen atom or two hydrogen atoms. Fig. 1 indicates the cerebral-blood-stream-­intensifying effect produced by administration of (±)-­2,6-diphenyl-3,7-dioxabicyclo[3.3.0]octane-4,8-dione (a mixture of cis isomer and the trans isomer in a ratio of 2 to 1).

  本发明公开了一种改善脑循环代谢功能的制剂，该制剂含有下式代表的 2,6-二苯基-3,7-二氧杂环[3.3.0]辛烷衍生物作为有效成分： 其中，R₁、R₃、R₄ 和 R₆ 各代表一个氢原子或一个低级烷氧基；R₂ 和 R₅ 各代表一个氢原子、一个 β-D-葡萄糖基或一个羟基；R₇ 和 R₈ 各代表一个氧原子或两个氢原子。 图 1 显示了服用(±)-2,6-二苯基-3,7-二氧双环[3.3.0]辛烷-4,8-二酮（顺式异构体和反式异构体的混合物，比例为 2 比 1）所产生的脑血流强化效应。
• US4816481A
  申请人：——

  公开号：US4816481A

  公开（公告）日：1989-03-28
• JP5914897
  申请人：——

  公开号：——

  公开（公告）日：——