1-(4-hydroxy-3-methoxyphenyl)butane-1,3-dione | 157340-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-hydroxy-3-methoxyphenyl)butane-1,3-dione
• 英文别名: 1-(4-Hydroxy-3-methoxyphenyl)-butane-1,3-dione
• CAS: 157340-27-7
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: HRMGIMMBNLHXPS-UHFFFAOYSA-N

物化性质

• 沸点：
  375.3±27.0 °C(predicted)
• 密度：
  1.199±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二甲氧基苯甲醛 、 1-(4-hydroxy-3-methoxyphenyl)butane-1,3-dione 在 boron trioxide 、 硼酸三甲酯 、 正丁胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以47%的产率得到(E)-5-(3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)pent-4-ene-1,3-dione
  参考文献：
  名称：

  Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids

  摘要：

  A click-type entry into shortened curcuminoids of the diarylpentanoid type has been developed. The reaction is ideally suited to generate non-symmetrical analogues of curcumin, a class of natural products difficult to access but of growing biomedical relevance and special mechanistic interest to investigate the unique binding mode of curcumin to tubulin. Investigation of a series of click diarylpentane curcuminoids and their pyrazole adducts in various cellular tubulin functional assays validated this class of compounds as a novel type of anti-mitotic agents, evidencing structure-activity relationships, and identifying the pyrazole adduct 4k as a promising lead. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.053

文献信息

• Chemical Compounds
  申请人：Rees David Daryl

  公开号：US20080045591A1

  公开（公告）日：2008-02-21

  Compounds of general formula I: wherein: R 1 and R 2 are, independently of each other, selected from hydrogen, optionally substituted C 1-10 alkyl, optionally substituted —CO—(C 1-10 alkyl), optionally substituted C 3-10 cycloalkyl, optionally substituted —CO—(C 3-10 cycloalkyl), optionally substituted C 2-10 alkenyl, optionally substituted —CO—(C 2-10 alkenyl), optionally substituted aryl, and optionally substituted —CO-aryl, or R 1 and R 2 together represent an optionally substituted saturated or unsaturated C 1-10 alkylidene group, or an optionally substituted saturated or unsaturated C 3-10 cycloalkylidene group, or R 1 and R 2 together with the carbon atom to which they are attached represent an optionally substituted saturated or unsaturated organic ring containing 3, 4, 5, 6, 7 or 8 ring carbon atoms and optionally 1, 2 or 3 ring heteroatoms selected from O, N and S; R 3 , which may be the same as, or different from, either of R 1 and R 2 , is selected from optionally substituted C 1-10 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted C 2-10 alkenyl, and optionally substituted aryl; R 4 , R 5 and R 6 are, independently of each other, selected from hydrogen, optionally substituted C 1-10 alkyl, OH, optionally substituted C 1-10 alkoxy, halo, optionally substituted aryloxy, optionally substituted (C 1-10 alkyl)-S(O) n — where n=0, 1 or 2, optionally substituted aryl-S(O) n — where n=0, 1 or 2, or R 4 is hydrogen and R 5 and R 6 together represent an optionally substituted saturated or unsaturated organic chain containing 1, 2, 3, 4, 5, 6 or 7 chain carbon atoms and optionally 1, 2 or 3 chain heteroatoms selected from O, N and S, provided that the chain is at least 3 atoms long; with the proviso that, when R 1 ═R 2 =hydrogen, then any optionally substituted C 1-10 alkyl or optionally substituted C 2-10 alkenyl for R 3 must have a branch point at one or more of the α and β positions counted from the carbonyl group (or tautomeric form thereof) to which R 3 is attached; or a physiologically acceptable salt, complex or prodrug thereof; are disclosed per se and for use in the treatment or prophylaxis of hypersensitivity, smooth muscle disorders, spasmodic conditions, allergic conditions, inflammatory conditions and/or pain.

  通式I的化合物： 其中： R1和R2独立地选自氢，可选取代的C1-10烷基，可选取代的—CO—（C1-10烷基），可选取代的C3-10环烷基，可选取代的—CO—（C3-10环烷基），可选取代的C2-10烯基，可选取代的—CO—（C2-10烯基），可选取代的芳基和可选取代的—CO-芳基，或者R1和R2一起代表一个可选取代的饱和或不饱和的C1-10烷基亚基，或一个可选取代的饱和或不饱和的C3-10环烷基亚基，或者R1和R2与它们连接的碳原子一起代表一个可选取代的含有3、4、5、6、7或8个环碳原子和可选取代的1、2或3个从O、N和S中选取的环杂原子的饱和或不饱和的有机环； R3可以与R1和R2中的任何一个相同或不同，选自可选取代的C1-10烷基，可选取代的C3-10环烷基，可选取代的C2-10烯基和可选取代的芳基； R4、R5和R6独立地选自氢，可选取代的C1-10烷基，OH，可选取代的C1-10烷氧基，卤素，可选取代的芳氧基，可选取代的（C1-10烷基）-S（O）n-，其中n=0、1或2，可选取代的芳基-S（O）n-，其中n=0、1或2，或者R4为氢，R5和R6一起代表一个可选取代的含有1、2、3、4、5、6或7个链碳原子和可选取代的1、2或3个链杂原子的饱和或不饱和的有机链，前提是该链至少由3个原子组成； 但是，当R1=R2=氢时，R3必须选取一个可选取代的C1-10烷基或可选取代的C2-10烯基，其中至少有一个分支点位于从R3所连接的羰基（或其互变异构体）计算的α和β位置之一；或其生理上可接受的盐、络合物或前药，本发明公开了其本身和用于治疗或预防过敏、平滑肌障碍、痉挛性疾病、过敏性疾病、炎症性疾病和/或疼痛。
• Chemical compounds
  申请人：Phytopharm PLC

  公开号：US07589123B2

  公开（公告）日：2009-09-15

  Compounds of general formula I: wherein: R1 and R2 are, independently of each other, selected from hydrogen, optionally substituted C1-10alkyl, optionally substituted —CO—(C1-10alkyl), optionally substituted C3-10cycloalkyl, optionally substituted —CO—(C3-10cycloalkyl), optionally substituted C2-10alkenyl, optionally substituted —CO—(C2-10alkenyl), optionally substituted aryl, and optionally substituted —CO-aryl, or R1 and R2 together represent an optionally substituted saturated or unsaturated C1-10alkylidene group, or an optionally substituted saturated or unsaturated C3-10cycloalkylidene group, or R1 and R2 together with the carbon atom to which they are attached represent an optionally substituted saturated or unsaturated organic ring containing 3, 4, 5, 6, 7 or 8 ring carbon atoms and optionally 1, 2 or 3 ring heteroatoms selected from O, N and S; R3, which may be the same as, or different from, either of R1 and R2, is selected from optionally substituted C1-10alkyl, optionally substituted C3-10cycloalkyl, optionally substituted C2-10alkenyl, and optionally substituted aryl; R4, R5 and R6 are, independently of each other, selected from hydrogen, optionally substituted C1-10alkyl, OH, optionally substituted C1-10 alkoxy, halo, optionally substituted aryloxy, optionally substituted (C1-10alkyl)-S(O)n— where n=0, 1 or 2, optionally substituted aryl-S(O)n— where n=0, 1 or 2, or R4 is hydrogen and R5 and R6 together represent an optionally substituted saturated or unsaturated organic chain containing 1, 2, 3, 4, 5, 6 or 7 chain carbon atoms and optionally 1, 2 or 3 chain heteroatoms selected from O, N and S, provided that the chain is at least 3 atoms long; with the proviso that, when R1═R2=hydrogen, then any optionally substituted C1-10alkyl or optionally substituted C2-10alkenyl for R3 must have a branch point at one or more of the α and β positions counted from the carbonyl group (or tautomeric form thereof) to which R3 is attached; or a physiologically acceptable salt, complex or prodrug thereof; are disclosed per se and for use in the treatment or prophylaxis of hypersensitivity, smooth muscle disorders, spasmodic conditions, allergic conditions, inflammatory conditions and/or pain.

  通式I的化合物，其中：R1和R2是独立选择的氢、可选择取代的C1-10烷基、可选择取代的—CO—（C1-10烷基）、可选择取代的C3-10环烷基、可选择取代的—CO—（C3-10环烷基）、可选择取代的C2-10烯基、可选择取代的—CO—（C2-10烯基）、可选择取代的芳基和可选择取代的—CO-芳基，或者R1和R2共同表示可选择取代的饱和或不饱和的C1-10烷基亚基，或可选择取代的饱和或不饱和的C3-10环烷基亚基，或者R1和R2与它们所附着的碳原子共同表示可选择取代的含3、4、5、6、7或8个环碳原子和可选择从O、N和S中选取1、2或3个环杂原子的有机环；R3可能与R1和R2中的任何一个相同或不同，选择可选择取代的C1-10烷基、可选择取代的C3-10环烷基、可选择取代的C2-10烯基和可选择取代的芳基；R4、R5和R6独立选择的是氢、可选择取代的C1-10烷基、OH、可选择取代的C1-10烷氧基、卤素、可选择取代的芳氧基、可选择取代的（C1-10烷基）-S（O）n-其中n = 0,1或2，可选择取代的芳基-S（O）n-其中n = 0,1或2，或者R4是氢，R5和R6共同表示可选择取代的含1、2、3、4、5、6或7个链碳原子和可选择从O、N和S中选取1、2或3个链杂原子的有机链，前提是链至少有3个原子长；但是，当R1═R2=氢时，R3的可选择取代的C1-10烷基或可选择取代的C2-10烯基必须在从R3所附着的羰基（或其互变异构体）计数的α和β位置中的一个或多个位置具有分支点；或其生理上可接受的盐、复合物或前药。本发明公开了该化合物本身及其在治疗或预防过敏、平滑肌障碍、痉挛性疾病、过敏症、炎症病症和/或疼痛方面的用途。
• DIOXO-ALKANES AND DIOXO-ALKENES
  申请人：PHYTOPHARM PLC

  公开号：EP2046311A2

  公开（公告）日：2009-04-15
• US7589123B2
  申请人：——

  公开号：US7589123B2

  公开（公告）日：2009-09-15
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：PHYTOPHARM PLC

  公开号：WO2008003978A2

  公开（公告）日：2008-01-10

  [EN] Compounds of general formula (I) wherein: R₁ and R₂ are, independently of each other, selected from hydrogen, optionally substituted C_1-10alkyl, optionally substituted -CO-(C_1-10alkyl), optionally substituted C_3-10cycloalkyl, optionally substituted -CO-(C_3-10cycloalkyl), optionally substituted C_2-10alkenyl, optionally substituted -CO-(C_2-10alkenyl), optionally substituted aryl, and optionally substituted -CO-aryl, or R₁ and R₂ together represent an optionally substituted saturated or unsaturated C_1-10alkylidene group, or an optionally substituted saturated or unsaturated C_3-10cycloalkylidene group, or R₁ and R₂ together with the carbon atom to which they are attached represent an optionally substituted saturated or unsaturated organic ring containing 3, 4, 5, 6, 7 or 8 ring carbon atoms and optionally 1, 2 or 3 ring heteroatoms selected from O, N and S; R₃, which may be the same as, or different from, either of R₁ and R₂, is selected from optionally substituted C_1-10alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted C_2-10alkenyl, and optionally substituted aryl; R₄, R₅ and R₆ are, independently of each other, selected from hydrogen, optionally substituted C_1-10alkyl, OH, optionally substituted C_1-10alkoxy, halo, optionally substituted aryloxy, optionally substituted (C_1-10alkyl)-S(O)_n- where n = 0, 1 or 2, optionally substituted aryl-S(O)_n- where n = 0, 1 or 2, or R₄ is hydrogen and R₅ and R₆ together represent an optionally substituted saturated or unsaturated organic chain containing 1, 2, 3, 4, 5, 6 or 7 chain carbon atoms and optionally 1, 2 or 3 chain heteroatoms selected from O, N and S, provided that the chain is at least 3 atoms long; with the proviso that, when R₁ = R₂ = hydrogen, then any optionally substituted C_1-10alkyl or optionally substituted C_2-10alkenyl for R₃ must have a branch point at one or more of the a and ß positions counted from the carbonyl group (or tautomeric form thereof) to which R₃ is attached; or a physiologically acceptable salt, complex or prodrug thereof; are disclosed per se and for use in the treatment or prophylaxis of hypersensitivity, smooth muscle disorders, spasmodic conditions, allergic conditions, inflammatory conditions and/or pain.
  [FR] L'invention concerne des composés de formule générale (I) dans laquelle : R₁ et R₂ sont chacun indépendamment de l'autre sélectionnés parmi un hydrogène, un alkyle en C_1-10 éventuellement substitué, un -CO-(alkyle en C_1-10) éventuellement substitué, un cycloalkyle en C_3-10 éventuellement substitué, un -CO-(cycloalkyle en C_3-10) éventuellement substitué, un alcényle en C_2-10 éventuellement substitué et un -CO-(alcényle en C_2-10) éventuellement substitué, un aryle éventuellement substitué, un -CO-aryle éventuellement substitué ou bien R₁ et R₂ représentent ensemble un groupe alkylidène en C_1-10 saturé ou insaturé éventuellement substitué ou un groupe cycloalkylidène en C_3-10 saturé ou insaturé éventuellement substitué ou bien R₁ et R₂ représentent ensemble avec l'atome de carbone auquel ils sont attachés un cycle organique saturé ou insaturé éventuellement substitué contenant 3, 4, 5, 6, 7 ou 8 atomes de carbone dans le cycle et éventuellement 1, 2 ou 3 hétéroatomes dans le cycle sélectionnés chacun parmi O, N et S ; R₃, lequel peut être identique ou différent de R₁ et de R₂, est sélectionné parmi un alkyle en C_1-10 éventuellement substitué, un cycloalkyle en C_3-10 éventuellement substitué, un alcényle en C_2-10 éventuellement substitué et un aryle éventuellement substitué ; R₄, R₅ et R₆ sont, chacun indépendamment les uns des autres, sélectionnés parmi un hydrogène, un alkyle en C_1-10 éventuellement substitué, OH, un alcoxy en C_1-10 éventuellement substitué, un halogéno, un aryloxy éventuellement substitué, un (alkye en C_1-10)-S(O)_n- éventuellement substitué où n = 0, 1 ou 2, un aryl-S(O)_n- éventuellement substitué où n = 0, 1 ou 2 ou bien R₄ est un hydrogène et R₅ et R₆ représentent ensemble une chaîne organique saturée ou insaturée éventuellement substituée contenant 1, 2, 3, 4, 5, 6 ou 7 atomes de carbone dans la chaîne et éventuellement 1, 2 ou 3 hétéroatomes dans la chaîne sélectionnés chacun parmi O, N et S, à condition que la chaîne ait une longueur d'au moins 3 atomes ; à condition que, lorsque R₁ = R₂ = un hydrogène, alors tout alkyle en C_1-10 éventuellement substitué ou tout alcényle en C_2-10 éventuellement substitué représenté par R₃ ait un point de ramification au niveau d'une ou de plusieurs des positions a et ß comptées à partir du groupe carbonyle (ou de la forme tautomère de celui-ci) auquel R₃ est attaché ; ou un sel, complexe ou promédicament acceptable du point de vue physiologique de ceux-ci ; en tant que tels et étant destinés à être utilisés dans le traitement ou la prophylaxie de l'hypersensibilité, de troubles des muscles lisses, d'affections spasmodiques, d'affections allergiques, d'affections inflammatoires et/ou de la douleur.