furfural curcuminoid | 92496-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: furfural curcuminoid
• 英文别名: (1E,6E)-1,7-Di-(2-furyl)-1,6-heptadiene-3,5-dione；1,7-Bis--hepta-1,6-dien-3,5-dion；1,7-di-furan-2-yl-hepta-1,6-diene-3,5-dione；1t,7t-di-[2]furyl-hepta-1,6-diene-3,5-dione；1t,7t-Di-[2]furyl-hepta-1,6-dien-3,5-dion；1,7-Di(furan-2-yl)-5-hydroxyhepta-1,4,6-trien-3-one；(1E,6E)-1,7-bis(furan-2-yl)hepta-1,6-diene-3,5-dione
• CAS: 92496-94-1
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: VVSPMCDLBJTCII-KQQUZDAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  furfural curcuminoid 在 盐酸 作用下， 以 水 为溶剂， 生成 1,7-di(furan-2-yl)-5-hydroxyhepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Synthesis and Identification of New 4-Arylidene Curcumin Analogues as Potential Anticancer Agents Targeting Nuclear Factor-κB Signaling Pathway

  摘要：

  A series of curcumin analogues including new 4-arylidene curcumin analogues (4-arylidene-1,7-bisarylhepta-1,6-diene-3,5-diones) were synthesized. Cell growth inhibition assays revealed that most 4-arylidene curcumin analogues can effectively decrease the growth of a panel of lung cancer cells at submicromolar and low micromolar concentrations. High content analysis technology coupled with biochemical studies showed that this new class of 4-arylidene curcumin analogues exhibits significantly improved NF-kappa B inhibition activity over the parent compound curcumin, at least in part by inhibiting I kappa B phosphorylation and degradation via IKK blockage; selected 4-arylidene curcumin analogues also reduced the tumorigenic potential of cancer cells in a clonogenic assay.

  DOI：

  10.1021/jm1004545
• 作为产物：
  描述：

  4-acetyl-1t,7t-di-[2]furyl-hepta-1,6-diene-3,5-dione 在 sodium hydroxide 、 二氧化碳 作用下， 生成 furfural curcuminoid
  参考文献：
  名称：

  Lampe et al., Chemicke Listy, 1932, vol. 26, p. 454,456

  摘要：

  DOI：

文献信息

• On Regioselectivity of Aldol Condensation of Aromatic Aldehydes with Borate Complex of Acetylacetone
  作者：Val V. Martichonok、Peter K. Chiang、Padraick J. Dornbush、Kirkwood M. Land

  DOI：10.1080/00397911.2013.850094

  日期：2014.5.3

  Abstract While cinnamoyl acetone 1 is obtained in good yield by a condensation of 3 molar excess of a borate complex of acetylacetone with benzaldehyde, products of Knoevenagel condensation 2 are predominantly obtained with furfural and 5-substituted furfurals. Cinnamoyl acetone 1 can be further condensed with furfural to form unsymmetrical curcuminoid 5. Compound 2a does not produce any new products

  摘要 虽然肉桂酰丙酮 1 是通过 3 摩尔过量的乙酰丙酮与苯甲醛的硼酸盐络合物缩合获得的，但 Knoevenagel 缩合 2 的产物主要通过糠醛和 5-取代的糠醛获得。肉桂酰丙酮1可以进一步与糠醛缩合形成不对称姜黄素5。化合物2a在相同条件下不产生任何新产物。化合物3和5是原生动物阴道毛滴虫生长的良好抑制剂。图形概要
• Efficient synthesis of multicyclic spirooxindoles via a cascade Michael/Michael/oxa-Michael reaction of curcumins and isatylidene malononitriles
  作者：Xiao-Gang Yin、Xin-Yun Liu、Zhi-Peng Hu、Ming Yan

  DOI：10.1039/c2ob06995d

  日期：——

  A cascade Michael/Michael/oxa-Michael reaction between curcumins and isatylidene malononitriles has been developed. Multicyclic spirooxindoles were prepared in excellent yields and diastereoselectivities. DMAP was found to catalyze this transformation efficiently under mild reaction conditions.

  已开发出姜黄素和异亚甲基丙二腈之间的迈克尔/迈克尔/氧桥迈克尔级联反应。多环螺吲哚以优异的产率和立体选择性制备。DMAP在温和的反应条件下可有效催化这一转化。
• [EN] PALLADIUM COMPLEXES OF CURCUMIN AND ITS ANALOGUES AND METHODS OF PREPARATION OF THE SAME<br/>[FR] COMPLEXES DE PALLADIUM DE LA CURCUMINE ET SES ANALOGUES, ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：UNIVERZITA KOMENSKEHO V BRATISLAVE

  公开号：WO2014175841A1

  公开（公告）日：2014-10-30

  The invention relates to palladium(II) complexes of curcumin and its analogues of general formula (Formula (A)) wherein R1 and R2 are each independently hydrogen, hydroxy, methoxy or ethoxy, as well as the process for preparing the same by reacting the complex compounds [(tmcyda)Pd(OAc)2 ] or [(dmpip)Pd(OAc)2] of general formula ((Formula (B) with curcumin or its analogues of general formula (Formula (B)) wherein R1 and R2 are the same as defined above, in an alcohol having 1 to 4 carbon atoms, or in chlorinated solvents, selected from the group comprising chloroform and dichloromethane, for 12 to 140 hours at the temperature of 15 to 50 °C.

  该发明涉及到姜黄素及其类似物的钯（II）络合物，其一般化学式为（化学式（A）），其中R1和R2分别独立地为氢、羟基、甲氧基或乙氧基，以及通过将一般化学式为（化学式（B））的复合物化合物[(tmcyda)Pd(OAc)2]或[(dmpip)Pd(OAc)2]与姜黄素或其一般化学式为（化学式（B））的类似物在1至4个碳原子的醇中，或在氯化溶剂（包括氯仿和二氯甲烷）中，在15至50°C的温度下反应12至140小时制备它们的方法。
• Diastereo- and enantioselective synthesis of densely functionalized cyclohexanones via double Michael addition of curcumins with nitroalkenes
  作者：Narasimham Ayyagari、Irishi N.N. Namboothiri

  DOI：10.1016/j.tetasy.2012.04.011

  日期：2012.4

  The asymmetric double Michael additions of curcumins to nitroalkenes to afford highly functionalized cyclohexanones have been carried out for the first time. A combination of a dihydrocinchonine-thiourea organocatalyst and K2CO3 was found to be the most effective in obtaining the desired cyclohexanones in good yield, diastereoselectivity and enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.