angustone A | 90686-13-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: angustone A
• 英文别名: 5,7,2',4'-Tetrahydroxy-6,3'-diprenylisoflavone；3-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
• CAS: 90686-13-8
• 化学式: C₂₅H₂₆O₆
• 分子量: 422.478
• InChiKey: KKFAKKIIFUFASS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  angustone A 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 4'-O-methylalpinumisoflavone
  参考文献：
  名称：

  羽扇豆根中的异黄酮

  摘要：

  摘要 两种新型异黄酮，5,7,2'-三羟基-6-(3,3-二甲基烯丙基)-[6",6"-二甲基吡喃(2",3":4',3')]-异黄酮和5 ,2',4'-三羟基-3'-(3,3-二甲基烯丙基)-[6",6"-二甲基吡喃(2",3":7,6)]异黄酮，已从羽扇豆的根中分离出来狭叶 联合收割机。通过分析 13 C NMR 和其他光谱数据，以及通过将其中一种化合物化学转化为香豆素色酮来确定结构。

  DOI：

  10.1016/s0031-9422(00)81531-9
• 作为产物：
  描述：

  5,7,4'-trihydroxy-2'-methoxy-6,3'-diprenylisoflavone 在 哌啶 、 硫酸 作用下， 反应 4.0h， 以3 mg的产率得到angustone A
  参考文献：
  名称：

  Flavonoids from Millettia pulchra

  摘要：

  DOI：

  10.1016/s0031-9422(00)80349-0

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• Fad-dependent epoxidase as a key enzyme in fungal metabolism of prenylated flavonoids
  作者：Mitsuharu Tanaka、Satoshi Tahara

  DOI：10.1016/s0031-9422(97)00322-1

  日期：1997.10

  Crude protein extracts from Botrytis cinerea preincubated with 6-prenylnaringenin (6-PN) for 20 hr catalysed the prenyl epoxidation of 7-O-methyl-luteone. The resulting epoxide was non-enzymatically and slowly converted into the corresponding dihydrofurano derivative in a buffer solution at pH 7.5. Preparation of cell-free extracts in the presence of 6-PN from the mycelia without preincubation with 6-PN hardly showed the epoxidizing activity. These facts revealed that the substrate analogue 6-PN has a role as an enzyme inducer rather than stabilizer. The enzyme reaction depends on molecular oxygen and NADPH. Low amounts of FAD were necessary for maximal enzyme activity. The enzymatic activity was not inhibited by various inhibitors of cytochrome P-450 tested, in addition to carbon monoxide and cytochrome c. The results indicated that this enzyme does not belong to the monooxygenases dependent on cytochrome P-450, but to those dependent on FAD. About half of. the total enzyme activity was found in the 125 000 g supernatant, but the specific activity for the epoxidation reaction in the 125 000 g pellet was 3.7-fold higher than in the soluble fraction. The enzyme showed high specificity to monoprenyl isoflavones. Finally, a preliminary experiment using a cell-free system from white lupin hypocotyls resulted in formation of small amounts of an epoxide corresponding to 7-O-methyl-luteone used as the substrate. (C) 1997 Elsevier Science Ltd.
• Fungitoxic dihydrofuranoisoflavones and related compounds in white lupin, Lupinus albus
  作者：Satoshi Tahara、John L. Ingham、Shiro Nakahara、Junya Mizutani、Jeffrey B. Harborne

  DOI：10.1016/s0031-9422(00)84936-5

  日期：1984.8
• Nakahara, Shiro; Tahara, Satoshi; Mizutani, Junya, Agricultural and Biological Chemistry, 1986, vol. 50, p. 863 - 874
  作者：Nakahara, Shiro、Tahara, Satoshi、Mizutani, Junya、Ingham, John L.

  DOI：——

  日期：——
• PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
  申请人：McMaster University

  公开号：US20210380513A1

  公开（公告）日：2021-12-09

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).