6-(3,4-dihydroxyphenyl)-hex-5-en-2,4-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 6-(3,4-dihydroxyphenyl)-hex-5-en-2,4-dione
• 英文别名: (5E)-6-(3,4-dihydroxyphenyl)hex-5-ene-2,4-dione；(E)-6-(3,4-dihydroxyphenyl)hex-5-ene-2,4-dione；hispolone
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: SEOGGTOIKLUNNM-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(3,4-dihydroxyphenyl)-hex-5-en-2,4-dione 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 反应 2.0h， 以77.5%的产率得到6-(3,4-dihydroxyphenyl)hexane-2,4-dione
  参考文献：
  名称：

  作为潜在的抗结核药物的组蛋白类似物的合成，筛选和对接分析。

  摘要：

  合成了一系列的20个Hispolons / dihydrohispolons，并通过光谱数据对其进行了表征。对这些化合物进行了针对结核分枝杆菌（H37Rv）菌株的体外抗结核活性筛选。合成的化合物显示出从100到1.6μg/ mL的变化的抗结核活性。在筛选出的化合物中，四种化合物（H1，H2，H3和H15）具有中等活性，MIC为25μg/ mL。观察到二氢hispolon衍生物H14（MIC1.6μg/ mL），然后是H13（6.25μg/ mL）和H17（12.5μg/ mL），H19（3.125μg/ ML）的活性。对接模拟对测试化合物与β-酮酰基合酶（mtbFabH）之间可能的相互作用提供了很好的见解。药物-抑制剂组合研究显示，与针对霉菌酸生物合成的药物没有协同作用（异烟肼，

  DOI：

  10.1016/j.bmcl.2016.11.047
• 作为产物：
  描述：

  乙酰丙酮 、 3,4-二羟基苯甲醛 在 硼酸三乙酯 、 boron trioxide 、 哌啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.5h， 以32%的产率得到6-(3,4-dihydroxyphenyl)-hex-5-en-2,4-dione
  参考文献：
  名称：

  Structure activity relationship study of curcumin analogues toward the amyloid-beta aggregation inhibitor

  摘要：

  Inhibition of the amyloid beta aggregation process could possibly prevent the onset of Alzheimer's disease. In this article, we report a structure-activity relationship study of curcumin analogues for anti amyloid beta aggregation activity. Compound 7, the ideal amyloid beta aggregation inhibitor in vitro among synthesized curcumin analogues, has not only potent anti amyloid beta aggregation effects, but also water solubility more than 160 times that of curcumin. In addition, new approaches to improve water solubility of curcumin-type compounds are proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.076

文献信息

• Hydroxyphenylalkadiones and Their Use for Masking Bitter Taste and/or for Intensifying Sweet Taste
  申请人：Ley Jakob

  公开号：US20080227866A1

  公开（公告）日：2008-09-18

  The use of a hydroxyphenylalkadione derivative of the formula (I) wherein, for X, a and Y: X is a —CH 2 —, —NH— or —O— group, Y is a —CH 2 — group and a is a single bond or X and Y are in each case a —CH— group and a is a double bond in the Z or E configuration, wherein, for R 1 , R 2 and R 3 R 1 denotes hydrogen, an aliphatic radical having 1 to 4 C atoms or a —O—R 5 , —S—R 5 or —NR 5 R 6 group and R 2 and R 3 independently of one another denote hydrogen or an alkyl having 1, 2, 3, 4 or 5 C atoms which is optionally substituted by one or more oxo groups or R 7 —O— groups or R 1 and R 2 together form an aliphatic ring which contains a total of 4 to 10 carbon atoms and 0 or 1 oxygen atom, wherein the ring constituent represented by R 1 and R 2 is optionally substituted by one or more oxo groups and/or R 7 —O— groups and/or aliphatic radicals having 1 to 4 C atoms and R 3 denotes hydrogen or an alkyl having 1, 2, 3, 4 or 5 C atoms which is optionally substituted by one or more oxo groups or R 7 —O— groups or R 2 and R 3 together form an aliphatic ring which contains a total of 4 to 10 carbon atoms and 0 or 1 oxygen atom, wherein the ring constituent represented by R 2 and R 3 is optionally substituted by one or more oxo groups and/or R 7 —O— groups and/or aliphatic radicals having 1 to 4 C atoms and R 1 denotes hydrogen, an aliphatic radical having 1 to 4 C atoms or a —O—R 5 , —S—R 5 or —NR 5 R 6 group, wherein, for R 4 and R: R 4 and R independently of one another denote hydrogen, methyl or ethyl and wherein, for R 5 , R 6 and R 7 : R 5 , R 6 and R 7 independently of one another denote hydrogen or an aliphatic radical having 1 to 4 C atoms, a salt of such a hydroxyphenylalkadione of the formula (I), a mixture comprising or consisting of two or more different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, a mixture comprising or consisting of salts of two or more different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, or a mixture comprising or consisting of a hydroxyphenylalkadione of the formula (I) or two or more different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, and a salt of a hydroxyphenylalkadione of the formula (I) or two or more salts of different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 in each case have the meaning given above, for modifying, masking or reducing the unpleasant flavour impression of an unpleasantly tasting substance and/or for intensifying the sweet taste of a sweet-tasting substance and/or the sweet odour impression of an aroma substance which causes a sweet odour impression, as well as formulations and processes including a hydroxyphenylalkadione of the formula (I), are described.

  本文描述了使用公式（I）的羟基苯基丙酮衍生物的用途，其中，对于X、a和Y： X是一个-CH2-，-NH-或-O-基团， Y是一个-CH2-基团， a是一个单键； 或者X和Y在每种情况下都是一个-CH-基团，并且在Z或E构型中有一个双键； 对于R1、R2和R3，它们分别表示氢、具有1至4个C原子的脂肪基或-O-R5、-S-R5或-NR5R6基团； R2和R3独立地表示氢或具有1、2、3、4或5个C原子的烷基，该烷基可以被一个或多个氧化基团或R7-O-基团取代； 或者R1和R2共同形成一个含有4至10个碳原子和0或1个氧原子的脂肪环，其中由R1和R2表示的环组分可以选择地被一个或多个氧化基团和/或R7-O-基团和/或具有1至4个C原子的脂肪基取代，而R3表示氢或具有1、2、3、4或5个C原子的烷基，该烷基可以被一个或多个氧化基团或R7-O-基团取代； 或者R2和R3共同形成一个含有4至10个碳原子和0或1个氧原子的脂肪环，其中由R2和R3表示的环组分可以选择地被一个或多个氧化基团和/或R7-O-基团和/或具有1至4个C原子的脂肪基取代； R1表示氢、具有1至4个C原子的脂肪基或-O-R5、-S-R5或-NR5R6基团； 对于R4和R： R4和R分别独立地表示氢、甲基或乙基； 对于R5、R6和R7： R5、R6和R7分别独立地表示氢或具有1至4个C原子的脂肪基； 本文还描述了使用公式（I）的羟基苯基丙酮衍生物的盐，包括或仅包括两种或两种以上不同的公式（I）的羟基苯基丙酮衍生物的混合物，其中X、a、Y、R、R1、R2、R3、R4、R5、R6和R7在每种情况下具有上述给定的含义，以及包括公式（I）的羟基苯基丙酮衍生物的制剂和过程，用于修改、掩盖或减少令人不愉快的味道物质的不愉快的口感印象，以及用于增强甜味物质的甜味和/或引起甜味印象的香气物质的甜味气味印象。
• HYDROXYPHENYLALKADIONES AND THEIR USE FOR MASKING BITTER TASTE AND/OR FOR INTENSIFYING SWEET TASTE
  申请人：Symrise GmbH & Co. KG

  公开号：EP1901618A1

  公开（公告）日：2008-03-26
• [EN] HYDROXYPHENYLALKADIONES AND THEIR USE FOR MASKING BITTER TASTE AND/OR FOR INTENSIFYING SWEET TASTE<br/>[FR] HYDROXYPHÉNYLALCADIONES ET LEUR UTILISATION POUR MASQUER UN GOÛT AMER ET/OU POUR INTENSIFIER UN GOÛT SUCRÉ
  申请人：SYMRISE GMBH & CO KG

  公开号：WO2007003527A1

  公开（公告）日：2007-01-11

  [EN] The use of a hydroxyphenylalkadione derivative of the formula (I) wherein, for X, a and Y: X is a -CH₂-, -NH- or -O- group, Y is a -CH₂- group and a is a single bond or X and Y are in each case a -CH- group and a is a double bond in the Z or E configuration, wherein, for R¹ , R² and R³ R¹ denotes hydrogen, an aliphatic radical having 1 to 4 C atoms or a -O-R⁵, -S-R⁵ or -NR⁵R⁶ group and R² and R³ independently of one another denote hydrogen or an alkyl having 1, 2, 3, 4 or 5 C atoms which is optionally substituted by one or more oxo groups or R⁷-O- groups or R¹ and R² together form an aliphatic ring which contains a total of 4 to 10 carbon atoms and 0 or 1 oxygen atom, wherein the ring constituent represented by R¹ and R² is optionally substituted by one or more oxo groups and/or R⁷-O- groups and/or aliphatic radicals having 1 to 4 C atoms and R³ denotes hydrogen or an alkyl having 1, 2, 3, 4 or 5 C atoms which is optionally substituted by one or more oxo groups or R⁷-O- groups or R² and R³ together form an aliphatic ring which contains a total of 4 to 10 carbon atoms and 0 or 1 oxygen atom, wherein the ring constituent represented by R² and R3 is optionally substituted by one or more oxo groups and/or R⁷-O- groups and/or aliphatic radicals having 1 to 4 C atoms and R¹ denotes hydrogen, an aliphatic radical having 1 to 4 C atoms or a -O-R⁵, -S-R⁵ or -NR⁵R⁶ group, wherein, for R⁴ and R: R⁴ and R independently of one another denote hydrogen, methyl or ethyl and wherein, for R⁵, R⁶ and R⁷: R⁵ R⁶ and R⁷ independently of one another denote hydrogen or an aliphatic radical having 1 to 4 C atoms, a salt of such a hydroxyphenylalkadione of the formula (I), a mixture comprising or consisting of two or more different hydroxy- phenylalkadiones of the formula (I), wherein X, a, Y, R, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ in each case have the meaning given above, a mixture comprising or consisting of salts of two or more different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ in each case have the meaning given above, or a mixture comprising or consisting of a hydroxyphenylalkadione of the formula (I) or two or more different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ in each case have the meaning given above, and a salt of a hydroxyphenylalkadione of the formula (I) or two or more salts of different hydroxyphenylalkadiones of the formula (I), wherein X, a, Y, R, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ in each case have the meaning given above, for modifying, masking or reducing the unpleasant flavour impression of an unpleasantly tasting substance and/or for intensifying the sweet taste of a sweet-tasting substance and/or the sweet odour impression of an aroma substance which causes a sweet odour impression, as well as formulations and processes including a hydroxyphenylalkadione of the formula (I), are described.
  [FR] La présente invention concerne l'utilisation d'un dérivé hydroxyphénylalcadione répondant à la formule (I) dans laquelle, en ce qui concerne X, a et Y : X représente un groupe -CH₂-, -NH- ou -O-, Y représente un groupe -CH₂- et a représente une liaison simple ou X et Y représentent dans chaque cas un groupe -CH- et a représente une liaison double en configuration Z ou E, où, en ce qui concerne R¹, R² et R³, R¹ représente un atome d'hydrogène, un radical aliphatique ayant 1 à 4 atomes de carbone ou un groupe -O-R⁵, -S-R⁵ ou -NR⁵R⁶ et R² et R³ représentent indépendamment l'un de l'autre un atome d'hydrogène ou un groupe alkyle ayant 1, 2, 3, 4 ou 5 atomes de carbone qui est éventuellement substitué par un ou plusieurs groupes oxo ou groupes R⁷-O- ou R¹ et R² forment ensemble un cycle aliphatique qui contient un total de 4 à 10 atomes de carbone et 0 ou 1 atome d'oxygène, où le constituant du cycle représenté par R¹ et R² est éventuellement substitué par un ou plusieurs groupes oxo et/ou groupes R⁷-O- et/ou radicaux aliphatiques ayant 1 à 4 atomes de carbone et R³ représente un atome d'hydrogène ou un groupe alkyle ayant 1, 2, 3, 4 ou 5 atomes de carbone qui est éventuellement substitué par un ou plusieurs groupes oxo ou groupes R⁷-O- ou R² et R³ forment ensemble un cycle aliphatique qui contient un total de 4 à 10 atomes de carbone et 0 ou 1 atome d'oxygène, où le constituant du cycle représenté par R² et R³ est éventuellement substitué par un ou plusieurs groupes oxo et/ou groupes R⁷-O- et/ou radicaux aliphatiques ayant 1 à 4 atomes de carbone et R¹ représente un atome d'hydrogène, un radical aliphatique ayant 1 à 4 atomes de carbone ou un groupe -O-R⁵, -S-R⁵ ou -NR⁵R⁶, où, en ce qui concerne R⁴ et R : R⁴ et R représentent indépendamment l'un de l'autre un atome d'hydrogène, un groupe méthyle ou éthyle et où, en ce qui concerne R⁵, R⁶ et R⁷ : R⁵, R⁶ et R⁷ représentent indépendamment les uns des autres un atome d'hydrogène ou un radical aliphatique ayant 1 à 4 atomes de carbone, un sel d'une telle hydroxyphénylalcadione répondant à la formule (I), un mélange comprenant ou se composant de deux ou plusieurs hydroxyphénylalcadiones différentes répondant à la formule (I), où X, a, Y, R, R¹, R², R³, R⁴, R⁵, R⁶ et R⁷ ont dans chaque cas la signification donnée ci-dessus, ou un mélange comprenant ou se composant d'une hydroxyphénylalcadione répondant à la formule (I) ou de deux ou plusieurs hydroxyphénylalcadiones différentes répondant à la formule (I), où X, a, Y, R, R¹, R², R³, R⁴, R⁵, R⁶ et R⁷ ont dans chaque cas la signification donnée ci-dessus, et un sel d'une hydroxyphénylalcadione répondant à la formule (I) ou deux ou plusieurs sels d'hydroxyphénylalcadiones différentes répondant à la formule (I), où X, a, Y, R, R¹, R², R³, R⁴, R⁵, R⁶ et R⁷ ont dans chaque cas la signification donnée ci-dessus, pour modifier, masquer ou réduire l'impression de saveur désagréable d'une substance ayant un goût désagréable et/ou pour intensifier le goût sucré d'une substance sucrée et/ou l'impression d'odeur sucrée d'une substance aromatique ce qui entraîne une impression d'odeur sucrée, ainsi que des formulations et des procédés comprenant une hydroxyphénylalcadione répondant à la formule (I).
• Structure activity relationship study of curcumin analogues toward the amyloid-beta aggregation inhibitor
  作者：Hitoshi Endo、Yuri Nikaido、Mamiko Nakadate、Satomi Ise、Hiroyuki Konno

  DOI：10.1016/j.bmcl.2014.10.076

  日期：2014.12

  Inhibition of the amyloid beta aggregation process could possibly prevent the onset of Alzheimer's disease. In this article, we report a structure-activity relationship study of curcumin analogues for anti amyloid beta aggregation activity. Compound 7, the ideal amyloid beta aggregation inhibitor in vitro among synthesized curcumin analogues, has not only potent anti amyloid beta aggregation effects, but also water solubility more than 160 times that of curcumin. In addition, new approaches to improve water solubility of curcumin-type compounds are proposed. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis, screening and docking analysis of hispolon analogs as potential antitubercular agents
  作者：Neduri V. Balaji、Bollikolla Hari Babu、Gottumukkala V. Subbaraju、Kurre Purna Nagasree、Muthyala Murali Krishna Kumar

  DOI：10.1016/j.bmcl.2016.11.047

  日期：2017.1

  series of 20 hispolons/dihydrohispolons were synthesized and characterized by spectral data. These compounds were subjected to in vitro antitubercular activity screening against Mycobacterium tuberculosis (H37Rv) strain. The synthesized compounds showed varied antitubercular activity ranging from 100 to 1.6μg/mL. Among the screened compounds, four compounds (H1, H2, H3 and H15) have shown moderate activity

  合成了一系列的20个Hispolons / dihydrohispolons，并通过光谱数据对其进行了表征。对这些化合物进行了针对结核分枝杆菌（H37Rv）菌株的体外抗结核活性筛选。合成的化合物显示出从100到1.6μg/ mL的变化的抗结核活性。在筛选出的化合物中，四种化合物（H1，H2，H3和H15）具有中等活性，MIC为25μg/ mL。观察到二氢hispolon衍生物H14（MIC1.6μg/ mL），然后是H13（6.25μg/ mL）和H17（12.5μg/ mL），H19（3.125μg/ ML）的活性。对接模拟对测试化合物与β-酮酰基合酶（mtbFabH）之间可能的相互作用提供了很好的见解。药物-抑制剂组合研究显示，与针对霉菌酸生物合成的药物没有协同作用（异烟肼，