(E)-7-hydroxy-3-(2',4'-dimethoxybenzylidene)chroman-4-one | 793724-32-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: (E)-7-hydroxy-3-(2',4'-dimethoxybenzylidene)chroman-4-one
• 英文别名: 7-hydroxy-3-(2,4-dimethoxybenzylidene)chroman-4-one；2'-methoxybonducellin；(e)-7-Hydroxy-3-(2',4'-dimethoxybenzylidene) chroman-4-one；(3E)-3-[(2,4-dimethoxyphenyl)methylidene]-7-hydroxychromen-4-one
• CAS: 793724-32-0
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: IWVNCSBPRZYLMJ-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-7-hydroxy-3-(2',4'-dimethoxybenzylidene)chroman-4-one 以 苯 为溶剂， 反应 4.0h， 以32%的产率得到(Z)-7-hydroxy-3-[(2,4-dimethoxyphenyl)methylene]-chroman-4-one
  参考文献：
  名称：

  异黄酮的合成，立体化学分配和生物活性。

  摘要：

  在四个步骤中，从适当取代的苯酚到苯并吡喃-4-酮合成了一系列四种天然存在的异黄酮类化合物和八种类似物。根据NMR光谱数据将产物指定为E-异构体。通过光异构化将E-异构体转化为Z-异构体。E-和Z-异构体显示出明显的化学位移，质子NMR光谱中（E）和（Z）-均异类黄酮之间的差异为确定立体化学提供了一种有用的方法。通过超氧化物歧化酶（NBT）和DPPH自由基清除方法测定了异黄酮类化合物的抗氧化活性。类似物7-羟基-3-[（3,4，5-三羟基苯基）亚甲基] chroman-4-one在这两种方法中均表现出优异的活性，其次是沙酮A，并且其效力比市售抗氧化剂如BHA，BHT等高出数倍。对这些化合物的体外抑制活性进行了评估-脂氧合酶（5-LOX）酶。发现类似物7-羟基-3-[（N，N-二甲基氨基苯基）亚甲基]苯并吡喃-4-酮具有有效的抑制活性，并且与标准的去甲二氢癸二酸相当。这些结果表明，这些同型异黄

  DOI：

  10.1016/j.bmc.2005.11.031
• 作为产物：
  描述：

  O-acetyl-2'-methoxybonducellin 在 silica-supported phosphomolybdic acid 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以94%的产率得到(E)-7-hydroxy-3-(2',4'-dimethoxybenzylidene)chroman-4-one
  参考文献：
  名称：

  系列“新型合成方法研究：”中的第148部分：使用二氧化硅负载的磷钼酸对醇，苯酚和胺进行选择性乙酰化和对芳香族乙酸酯进行选择性脱保护

  摘要：

  发现环保的二氧化硅负载的磷钼酸是在没有任何溶剂的情况下用于醇，酚和胺的选择性乙酰化以及在非常温和的条件下用于芳族乙酸酯的化学选择性脱保护的高效催化剂。该方法已用于保护羟基以及几种天然存在的生物活性酚类化合物的乙酸酯的脱保护。该催化剂可以容易地回收和再利用。

  DOI：

  10.1002/adsc.200700292

文献信息

• Isolation, Synthesis, and Bioactivity of Homoisoflavonoids from Caesalpinia pulcherrima
  作者：Biswanath Das、Ponnaboina Thirupathi、Bommena Ravikanth、Rathod Aravind Kumar、Akella Venkata Subramanya Sarma、Shaik Jilani Basha

  DOI：10.1248/cpb.57.1139

  日期：——

  One new homoisoflavonoid, (3E)-2,3-dihydro-6,7-dimethoxy-3[(3-hydroxy-4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one and four naturally new analogues, (3E)-3-(1,3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one, (3E)-3-(1,3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-methoxy-4H-1-benzopyran-4-one, (3E)-2,3-dihydro-7-hydroxy-3-[(3-hydroxy-4-methoxyphenyl)methylene]-4H-1-benzopyran-4-one and (3E)-2,3-dihydro-3-[(3,4-dimethoxyphenyl)methylene]-7-methoxy-4H-1-benzopyran-4-one, along with four known homoisoflavonoids, bonducellin, sappanone A, 2′-methoxybonducellin and 7-O-methylbonducellin were isolated from aerial parts of Caesalpinia pulcherrima. The structures of the new compounds were elucidated by interpretation of their 1D and 2D NMR spectra. Syntheses of the naturally new compounds and the known compounds have also been accomplished. The antibacterial and antifungal activities of the isolated homoisoflavonoids were studied.

  一种新的同异黄酮，(3E)-2,3-二氢-6,7-二甲氧基-3[(3-羟基-4-甲氧基苯基)亚甲基]-4H-1-苯并吡喃-4-酮和四种天然新类似物，(3E)-3-(1、3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one, (3E)-3-(1,3-benzodioxol-5-ylmethylene)-2,3-dihydro-7-methoxy-4H-1-benzopyran-4-one, (3E)-2,3-羟基-3-[(3-羟基-4-甲氧基苯基)亚甲基]-4H-1-苯并吡喃-4-酮和 (3E)-2,3-二氢-3-[(3,4-二甲氧基苯基)亚甲基]-7-甲氧基-4H-1-苯并吡喃-4-酮、从 Caesalpinia pulcherrima 的气生部分中分离出了 (3,3-二氢-2,3-二氢-3-[(3,4-二甲氧基苯基亚甲基]-7-甲氧基-4H-1-苯并吡喃-4-酮)，以及四种已知的同异黄酮类化合物：bonducellin、sappanone A、2′-甲氧基bonducellin 和 7-O-甲基bonducellin。通过解释这些新化合物的一维和二维核磁共振光谱，阐明了它们的结构。此外，还完成了天然新化合物和已知化合物的合成。研究了分离出的同异黄酮类化合物的抗菌和抗真菌活性。
• Stimulating the production of homoisoflavonoids in cell suspension cultures of Caesalpinia pulcherrima using cork tissue
  作者：Ping Zhao、Yuko Iwamoto、Isao Kouno、Yasukuni Egami、Hirobumi Yamamoto

  DOI：10.1016/j.phytochem.2004.08.004

  日期：2004.9

  It has previously been demonstrated that cork tissue increases the efficiency of the production of lipophilic secondary metabolites in diverse plant cell suspension cultures. In the present study, three new homoisoflavonoids - named dihydrobonducellin, 2'-methoxydihydrobonducellin, and 2'-methoxybonducellin - and bonducellin and isobonducellin were isolated from Caesalpinia pulcherrima cultured cells coincubated with cork tissue. Cork tissue increased the production of 2'-methoxybonducellin by about 7-fold relative to control cells, and more than 80% of the product was recoverable from the cork tissue. When cork tissue and methyl jasmonate or yeast extract were added simultaneously to the medium, the amount of 2'-methoxybonducellin produced increased further. The production of the other four homoisoflavonoids was enhanced by variable amounts. Our results indicate that the addition of cork tissue would be an effective technique for investigating formation of secondary metabolites that usually accumulate only in trace amounts. (C) 2004 Elsevier Ltd. All rights reserved.
• Part 148 in the Series “Studies on Novel Synthetic Methodologies:” Selective Acetylation of Alcohols, Phenols and Amines and Selective Deprotection of Aromatic Acetates using Silica-Supported Phosphomolybdic Acid
  作者：Biswanath Das、Ponnaboina Thirupathi、Rathod Aravind Kumar、Keetha Laxminarayana

  DOI：10.1002/adsc.200700292

  日期：2007.12.10

  efficient catalyst for the selective acetylation of alcohols, phenols and amines in the absence of any solvent and also for the chemoselective deprotection of aromatic acetates under very mild conditions. This method has been used for the protection of the hydroxy groups as well as for the deprotection of the acetates of several naturally occurring bioactive phenolic compounds. The catalyst can be easily

  发现环保的二氧化硅负载的磷钼酸是在没有任何溶剂的情况下用于醇，酚和胺的选择性乙酰化以及在非常温和的条件下用于芳族乙酸酯的化学选择性脱保护的高效催化剂。该方法已用于保护羟基以及几种天然存在的生物活性酚类化合物的乙酸酯的脱保护。该催化剂可以容易地回收和再利用。
• Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids
  作者：Vidavalur Siddaiah、Chunduri Venkata Rao、Somepalli Venkateswarlu、Alluri V. Krishnaraju、Gottumukkala V. Subbaraju

  DOI：10.1016/j.bmc.2005.11.031

  日期：2006.4

  vitro for their inhibitory activities against 5-lipoxygenase (5-LOX) enzyme. The analog 7-hydroxy-3-[(N,N-dimethylaminophenyl)methylene]chroman-4-one was found to possess potent inhibitory activity and was comparable to that of the standard, nordihydroguiaretic acid. These results suggest that these homoisoflavonoids, with their potent antioxidant and 5-LOX inhibitory activities, may have useful applications

  在四个步骤中，从适当取代的苯酚到苯并吡喃-4-酮合成了一系列四种天然存在的异黄酮类化合物和八种类似物。根据NMR光谱数据将产物指定为E-异构体。通过光异构化将E-异构体转化为Z-异构体。E-和Z-异构体显示出明显的化学位移，质子NMR光谱中（E）和（Z）-均异类黄酮之间的差异为确定立体化学提供了一种有用的方法。通过超氧化物歧化酶（NBT）和DPPH自由基清除方法测定了异黄酮类化合物的抗氧化活性。类似物7-羟基-3-[（3,4，5-三羟基苯基）亚甲基] chroman-4-one在这两种方法中均表现出优异的活性，其次是沙酮A，并且其效力比市售抗氧化剂如BHA，BHT等高出数倍。对这些化合物的体外抑制活性进行了评估-脂氧合酶（5-LOX）酶。发现类似物7-羟基-3-[（N，N-二甲基氨基苯基）亚甲基]苯并吡喃-4-酮具有有效的抑制活性，并且与标准的去甲二氢癸二酸相当。这些结果表明，这些同型异黄