2-羟基-9-(4-羟基苯基)-1H-萘嵌苯-1-酮 | 56252-02-9

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-羟基-9-(4-羟基苯基)-1H-萘嵌苯-1-酮
• 英文名称: 2-hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-1-one
• 英文别名: hydroxyanigorufone；emenolone；2-hydroxy-9-(4-hydroxyphenyl)phenalen-1-one
• CAS: 56252-02-9
• 化学式: C₁₉H₁₂O₃
• 分子量: 288.302
• InChiKey: HTELDEYOMOTOBI-UHFFFAOYSA-N

物化性质

• 熔点：
  201-204℃
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 2-羟基-9-(4-羟基苯基)-1H-萘嵌苯-1-酮 生成 2-methoxy-9-(4'-methoxyphenyl)phenalen-1-one
  参考文献：
  名称：

  Cooke,R.G.; Thomas,R.L., Australian Journal of Chemistry, 1975, vol. 28, p. 1053 - 1057

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3-(naphthalen-1-yl)acrylic acid 在 叔丁基过氧化氢 、 aluminum (III) chloride 、 草酰氯 、 三溴化硼 、 苄基三甲基氢氧化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 8.17h， 生成 2-羟基-9-(4-羟基苯基)-1H-萘嵌苯-1-酮
  参考文献：
  名称：

  Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer

  摘要：

  Concise total syntheses of the natural phytoalexins 2-hydroxy-8-(4-hydroxyphenyl)phenalen-1-one (1), 2-hydroxy-8-(3,4-dihydroxyphenyl)phenalen-1-one (2), and hydroxyanigorufone (4), together with regioisomer 3 are accomplished in 11 or 12 steps. The synthetic strategy features a Friedel Crafts acylation to construct the 1H-phenalen-1-one tricyclic core followed by a Suzuki cross-coupling to obtain the target compounds.

  DOI：

  10.1021/acs.jnatprod.7b00709

文献信息

• Phenylphenalenone-type Phytoalexins from Unripe Buñgulan Banana Fruit
  作者：Tsunashi KAMO、Nagomi KATO、Nobuhiro HIRAI、Mitsuya TSUDA、Daie FUJIOKA、Hajime OHIGASHI

  DOI：10.1271/bbb.62.95

  日期：1998.1

  Fourteen phenylphenalenone-type phytoalexins (1-14), including three new compounds, were isolated from the peel of unripe Musa acuminata [AAA] cv. Buñgulan fruit which had been injured and then inoculated with conidia of Colletotrichum musae. These new phytoalexins were identified as (+)-cis-2,3-dihydro-2,3-dihydroxy-4-(4′-hydroxyphenyl)phenalen-1-one (12), 9-(3′,4′-dimethoxyphenyl)-2-methoxyphenalen-1-one (13) and 9-(4′-hydroxyphenyl)-2-methoxyphenalen-1-one (14). The ratios of the relative intensities of the [M]+/[M-H]+ ions or [M-H2O]+/[M-H2O-H]+ ions in the EI mass spectra were applied to discriminate between 4- and 9-phenylphenalenones. An antifungal test on the phytoalexins showed that a phenolic hydroxyl group was essential for the activity.

  从未熟的麝香草 [AAA] cv. Buñgulan 果实的果皮中分离出 14 种苯丙芘酮类植物毒素（1-14），其中包括三种新化合物。Buñgulan 果实受伤后接种了 Colletotrichum musae 的分生孢子。这些新的植物毒素被鉴定为 (+)-cis-2,3-dihydro-2,3-dihydroxy-4-(4′-hydroxyphenyl)phenalen-1-one (12)、9-(3′,4′-dimethoxyphenyl)-2-methoxyphenalen-1-one (13) 和 9-(4′-hydroxyphenyl)-2-methoxyphenalen-1-one (14)。利用电离质谱中[M]+/[M-H]+离子或[M- ]+/[M-H2O-H]+离子的相对强度比来区分 4-苯基和 9-苯基苯丙烯酮。对植物醛毒素进行的抗真菌测试表明，酚羟基对其活性至关重要。
• Variability of phenylpropanoid precursors in the biosynthesis of phenylphenalenones in Anigozanthos preissii
  作者：Bettina Schmitt、Dirk Hölscher、Bernd Schneider

  DOI：10.1016/s0031-9422(99)00544-0

  日期：2000.2

  using 13C labelled precursors and NMR spectroscopic studies revealed general biosynthetic incorporation of phenylalanine and variable incorporation of cinnamic acid, p-coumaric acid, caffeic acid and ferulic acid into phenylphenalenones in root cultures of Anigozanthos preissii. Evidence was obtained for parallel pathways of phenylphenalenone biosynthesis, with respect to the left phenylpropanoid unit,

  使用 13 C 标记前体的饲养实验和 NMR 光谱研究揭示了苯丙氨酸的一般生物合成掺入和肉桂酸、对香豆酸、咖啡酸和阿魏酸在 Anigozanthos preissii 根培养物中可变掺入苯酚中。获得了关于左苯丙烷单元的苯苯​​酮生物合成平行途径的证据，以及涉及利用对香豆酸与右苯丙烷单元中的中间儿茶酚部分的后期生成的序列。
• Uses of hydroxyanigorufone
  申请人：TCI CO., LTD

  公开号：US10646455B2

  公开（公告）日：2020-05-12

  A method for at least one of increasing the synthesis of melatonin and promoting the secretion of melatonin is provided, wherein the method comprises administering to a subject in need an effective amount of a compound of formula (I): A method for at least one of treating diseases related to neurometabolic disorder, preventing diseases related to neurometabolic disorder, regulating appetite, regulating mood, regulating vasoconstriction, regulating hemostatic function and regulating immune response is also provided, wherein the method comprises administering to a subject in need an effective amount of a compound of formula (I) as described above.

  提供了一种用于增加褪黑激素合成和促进褪黑激素分泌中至少一种的方法，其中该方法包括向有需要的受试者施用有效量的式 (I) 化合物： 还提供了一种用于治疗与神经代谢紊乱有关的疾病、预防与神经代谢紊乱有关的疾病、调节食欲、调节情绪、调节血管收缩、调节止血功能和调节免疫反应中至少一种的方法，其中该方法包括向有需要的受试者施用有效量的上述式（I）化合物。
• Method of increasing melatonin synthesis to treat insomnia, ameliorate sleep disturbance and regulate sleep
  申请人：TCI CO., LTD.

  公开号：US10905674B2

  公开（公告）日：2021-02-02

  A method for at least one of increasing the synthesis of melatonin and promoting the secretion of melatonin is provided, wherein the method comprises administering to a subject in need an effective amount of a compound of formula (I): A method for at least one of treating diseases related to neurometabolic disorder, preventing diseases related to neurometabolic disorder, regulating appetite, regulating mood, regulating vasoconstriction, regulating hemostatic function and regulating immune response is also provided, wherein the method comprises administering to a subject in need an effective amount of a compound of formula (I) as described above.

  提供了一种用于增加褪黑激素合成和促进褪黑激素分泌中至少一种的方法，其中该方法包括向有需要的受试者施用有效量的式 (I) 化合物： 还提供了一种用于治疗与神经代谢紊乱有关的疾病、预防与神经代谢紊乱有关的疾病、调节食欲、调节情绪、调节血管收缩、调节止血功能和调节免疫反应中至少一种的方法，其中该方法包括向有需要的受试者施用有效量的上述式（I）化合物。
• Intermediates with biosynthetic implications in de novo production of phenyl-phenalenone-type phytoalexins by Musa acuminata revised structure of emenolone
  作者：Javier G. Luis、Winston Q. Fletcher、Fernando Echeverri、Teresa A. Grillo、Aurea Perales、JoséA. González

  DOI：10.1016/0040-4020(95)00129-v

  日期：1995.4

  Three new intermediates (1 - 3) in de novo biosynthetic pathway to phenyl-phenalenone-type phytoalexins have been isolated from rhizomes of Musa acuminata infected with the fungus Fusarium oxysporum. The structures of the new pre-phytoalexins were elucidated on the basis of spectroscopic evidences, chemical correlation and acid catalyzed biomimetic cyclization of 1 to emenolone (4), isolated from the same source and whose previously reported structure has been unambiguously corrected by X-ray diffraction analysis. The chemical shift for all of the hydrogen and carbon atoms in the substances were unambiguously established by mono- and bidimensional, homo- and heteronuclear NMR experiments (H-1 NMR, (1)3C NMR, COSY, ROESY, HMQC and HMBC).