3,4-bis-benzyloxy-benzoic acid-anhydride | 1592-48-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-bis-benzyloxy-benzoic acid-anhydride
• 英文别名: 3,4-Bis-benzyloxy-benzoesaeure-anhydrid；3,4-Dibenzyloxybenzoic acid anhydride；[3,4-bis(phenylmethoxy)benzoyl] 3,4-bis(phenylmethoxy)benzoate
• CAS: 1592-48-9
• 化学式: C₄₂H₃₄O₇
• 分子量: 650.728
• InChiKey: GJISPMMUPZFSON-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C
• 沸点：
  811.5±65.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4-bis-benzyloxy-benzoic acid-anhydride 在 palladium on activated charcoal 氢氧化钾 、 potassium-<3,4-bis-benzyloxy benzoate> 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 8.33h， 生成 3',4',7-trihydroxy-3,5,8-trimethoxyflavone
  参考文献：
  名称：

  Studies of the selective O-alkylation and dealkylation of flavonoids. 10. Selective demethylation of 7-hydroxy-3,5,8-trimethoxyflavones with anhydrous aluminum halide in acetonitrile or ether

  摘要：

  DOI：

  10.1021/jo00230a009
• 作为产物：
  描述：

  3,5-二苄氧基苯甲酸甲酯 在 氢氧化钾 、 氯化亚砜 作用下， 生成 3,4-bis-benzyloxy-benzoic acid-anhydride
  参考文献：
  名称：

  Shimizu; Ohta, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 1485,1487

  摘要：

  DOI：

文献信息

• An Improved Synthesis of the Anti-Picornavirus Flavone 3-O-Methylquercetin
  作者：Frank Boers、Bo-Liang Deng、Guy Lemière、Jozef Lepoivre、Alex De Groot、Roger Dommisse、Arnold J. Vlietinck

  DOI：10.1002/ardp.19973300909

  日期：——

  Two optimised procedures to synthesise 3‐O‐methylquercetin (1), an important antivirally active flavone, are presented: one is based on an Allan‐Robinson condensation, the other one on a modified phase transfer catalysed Baker‐ Venkataraman transformation.

  介绍了合成 3-O-甲基槲皮素 (1)（一种重要的抗病毒活性黄酮）的两种优化程序：一种基于 Allan-Robinson 缩合，另一种基于改进的相转移催化 Baker-Venkataraman 转化。
• Synthesis of 5,8-dihydroxy-6,7-dimethoxyflavones and revised structures for some natural flavones
  作者：T Horie

  DOI：10.1016/0031-9422(95)00070-n

  日期：1995.7

  7-trimethoxyflavones were synthesized from 2′,5′-dihydroxy-3′,4′,6′-trimethoxyacetophenone by adapting the selective O -alkylation and dealkylation, and the differentiation between the flavones and their isomeric 6-hydroxyflavones was clarified by 1 H NMR and UV spectra. Four natural flavones proposed as 5,8-dihydroxy-6,7-dimethoxyflavones, must have other structures and three are shown to be the isomeric

  摘要 以 2',5'-二羟基-3',4',6'-三甲氧基苯乙酮为原料，合成了 6 个 5,8-二羟基-6,7-二甲氧基黄酮和 3 个 8-羟基-5,6,7-三甲氧基黄酮。选择性O-烷基化和脱烷基化，黄酮和它们的异构体6-羟基黄酮之间的区别通过 1 H NMR 和紫外光谱得到澄清。四种天然黄酮被提议为 5,8-二羟基-6,7-二甲氧基黄酮，必须具有其他结构，其中三种被证明是异构的 5,7-二羟基-6,8-二甲氧基黄酮。从 Ageratum conyzoides 中分离出的黄酮被正确识别为 8-hydroxy-5,6,7,3',4',5'-六甲氧基黄酮，但从蜡菊中分离出的黄酮的结构被修改为异构体 7 -羟基-5,6,8-三甲氧基黄酮。
• 3-hydroxyflavones: their preparation and therapeutic application
  申请人：Societe Cortial, S.A.

  公开号：US04591600A1

  公开（公告）日：1986-05-27

  This invention relates to quercetin or fisetin derivatives substituted on the oxygen in the 3 position by groups such as lower alkyl, cycloalkyl, methanesulfonyl or paratoluenesulfonyl. The derivatives substituted by methanesulfonyl or paratoluenesulfonyl are obtained from a 3-O-glycoside whose phenol OH groups are blocked in the form of benzoate, and from which the OH in the 3 position is released by the action of concentrated HCl; this OH is esterified by mesityl chloride or paratoluenesulfonic acid chloride, and the benzoate groups are eliminated by soda treatment. The O derivatives substituted by alkyl or cycloakyl are prepared from a suitably substituted acetonitrile or metadiphenol; the resulting derivative reacts with 3,4-dibenzyloxybenzoic acid and the resulting flavone is debenzylated by hydrogenolysis. The derivatives, object of this invention, are useful in preventive or curative therapy of ocular and nervous complications from diabetes and are also useful as hypolipidemic or hypoglycemic agents.

  本发明涉及在3位氧原子上被低烷基、环烷基、甲烷磺酰基或对甲苯磺酰基等基团取代的槲皮素或黄酮类衍生物。由甲烷磺酰基或对甲苯磺酰基取代的衍生物是从3-O-糖苷中获得的，其酚羟基以苯甲酸酯的形式被阻断，通过浓盐酸的作用释放3位的羟基，这个羟基被甲基苯基氯化物或对甲苯磺酸氯化物酯化，苯甲酸酯基团被苏打处理消除。由烷基或环烷基取代的O衍生物是从适当取代的乙腈或间二苯酚制备的，得到的衍生物与3,4-二苯氧基苯甲酸反应，生成的黄酮类化合物经氢解反应去除苯基。本发明的衍生物在预防或治疗糖尿病引起的眼部和神经并发症方面有用，并且也有用作降脂或降糖剂。
• Syntheses of 5,7,8- and 5,6,7-trioxygenated 3-alkyl-3',4'-dihydroxyflavones and their inhibitory activities against arachidonate 5-lipoxygenase
  作者：Tokunaru Horie、Hideaki Tominaga、Yasuhiko Kawamura、Takahiko Hada、Natsuo Ueda、Yumi Amano、Shozo Yamamoto

  DOI：10.1021/jm00111a037

  日期：1991.7

  5,6,7- and 5,7,8-Trioxygenated 3',4'-dihydroxyflavones were derivatized by introducing alkyl groups of various chain lengths at the 3-position of the flavone skeleton. These compounds were tested as inhibitors for arachidonate 5-lipoxygenase purified from porcine leukocytes. Modification of the 3-position with an alkyl group of 6-10 carbons markedly decreased the IC50 values. 3-Hexyl-3',4'-dihydroxy-5,7,8-trimethoxyflavone inhibited 5-lipoxygenase with an IC50 value of 58 nM. The platelet and leukocyte 12-lipoxygenases, 15-lipoxygenase of reticulocytes, and cyclooxygenase of vesicular gland were inhibited less potently (IC50 = 0.4, 0.4, 2.7, and 30-mu-M). Thus, the compound was a relatively selective inhibitor for 5-lipoxygenase.
• Horie, Tokunaru; Tsukayama, Masao; Kawamura, Yasuhiko, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 11, p. 4465 - 4472
  作者：Horie, Tokunaru、Tsukayama, Masao、Kawamura, Yasuhiko、Yamamoto, Shigeo

  DOI：——

  日期：——