1E,3E-1,7-diphenylheptadien-5-ol | 58506-34-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1E,3E-1,7-diphenylheptadien-5-ol
• 英文别名: trans,trans-1,7-diphenyl-1,3-heptadien-5-ol；(E,E)-1,7-diphenylhepta-1,3-dien-5-ol；(4E,6E)-1,7-diphenylhepta-4,6-dien-3-ol
• CAS: 58506-34-6
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: OVURIZIJDDTXJS-FNCQTZNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1E,3E-1,7-diphenylheptadien-5-ol 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 生成 Acetic acid (2E,4E)-1-phenethyl-5-phenyl-penta-2,4-dienyl ester
  参考文献：
  名称：

  Non-Phenolic Linear Diarylheptanoids fromCurcuma xanthorrhiza: A Novel Type of Topical Anti-Inflammatory Agents: Structure-Activity Relationship

  摘要：

  三种非酚类线性1,7-二苯基庚烷酮的局部抗炎活性在小鼠模型中进行了评估，该模型以乙基苯丙酰胺引起的耳部水肿为基础。这些化合物之前是在一种泰国药用植物黄姜（Curcuma xanthorrhiza，姜科）中分离出的，并且还评估了四种新的半合成衍生物。自然存在的化合物1E,3E,1,7-二苯基庚烯-5-酮（6）表现出最强的抗炎活性，其ID50值与参考药物氧苯丁酮相似（分别为67与46 µg/耳）。没有任何半合成的二苯基庚烷酮的活性超过6。天然和半合成衍生物的化学结构和药理数据确立了明显的结构-活性关系。发现C7链中1和3号位的未饱和程度，以及5号位的氧化官能团的性质在决定观察到的体内活性中起着重要作用。基于这些发现，非酚类线性1,7-二苯基庚烷酮被建议代表一种新型的局部抗炎药物类。

  DOI：

  10.1055/s-2006-957867
• 作为产物：
  描述：

  桤木酮 在 sodium tetrahydroborate 、 乙醇 作用下， 反应 4.0h， 以80%的产率得到1E,3E-1,7-diphenylheptadien-5-ol
  参考文献：
  名称：

  Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids

  摘要：

  Four linear nonphenolic diarylheptanoids were synthesized and their antibacterial activities were studied. (S)-2-Me-CBS-catalysed reduction of alnustone with BH3.SMe2 gave (R) (-)(4E,6E)-1,7-diphenylhepta-4,6-dien-3-ol, a natural product. Reduction of alnustone with Na in t-BuOH at -15 degrees C under NH3 atm gave ( E)-1,7-diphenylhept-5-en-3-one as a Birch-type reduction product. t-BuOK catalysed condensation of benzalacetone with propionyl chloride gave (4Z,6E)-5-hydroxy-1,7-diphenylhepta-4,6-dien-3-one, a natural product. (1E,4Z,6E)-5-Hydroxy-4-phenethyl-1,7-diphenylhepta-1,4,6-trien-3-one, a curcuminoid, was synthesized starting from pentan-2,4-dione in 3 steps. The synthesized chemical compounds were applied against 2 gram-positive bacteria (Bacillus cereus and Arthrobacter agilis), 4 gram-negative bacteria (Pseudomonas aeruginosa, Xanthomonas campestris, Klebsiella oxytoca, and Helicobacter pylori), and 1 yeast (Candida albicans) by the disc diffusion method. All of the synthesized compound exhibited different degrees of antimicrobial activity at concentrations between 20-100 mu g/disc against the test organisms.

  DOI：

  10.3906/kim-1911-61

文献信息

• Electrochemical Nozaki–Hiyama–Kishi Coupling: Scope, Applications, and Mechanism
  作者：Yang Gao、David E. Hill、Wei Hao、Brendon J. McNicholas、Julien C. Vantourout、Ryan G. Hadt、Sarah E. Reisman、Donna G. Blackmond、Phil S. Baran

  DOI：10.1021/jacs.1c03007

  日期：2021.6.30

  practical using an electroreductive manifold. Although early studies pointed to the feasibility of such a process, those precedents were never applied by others due to cumbersome setups and limited scope. Here we show that a carefully optimized electroreductive procedure can enable a more sustainable approach to NHK, even in an asymmetric fashion on highly complex medicinally relevant systems. The e-NHK

  最常用的 C-C 键形成方法之一是使用还原歧管，使卤乙烯与 Ni 和 Cr 催化的醛偶联（Nozaki-Hiyama-Kishi，NHK）变得更加实用。尽管早期研究指出了这种过程的可行性，但由于设置繁琐且范围有限，这些先例从未被其他人应用。在这里，我们展示了经过精心优化的电还原程序可以使 NHK 采用更可持续的方法，即使在高度复杂的医学相关系统上以不对称方式也是如此。当传统化学技术失败时，e-NHK 甚至可以使非规范底物类别（例如氧化还原活性酯）参与低负载量的 Cr。详细的动力学、循环伏安法、
• KATO, NOBUHARU;HAMADA, YASUMASA;SHIOIRI, TAKAYUKI, CHEM. AND PHARM. BULL., 1984, 32, N 8, 3323-3326
  作者：KATO, NOBUHARU、HAMADA, YASUMASA、SHIOIRI, TAKAYUKI

  DOI：——

  日期：——
• NMR-Based Metabolic Profiling of <i>Anigozanthos</i> Floral Nectar
  作者：Dirk Hölscher、Silke Brand、Michael Wenzler、Bernd Schneider

  DOI：10.1021/np0705514

  日期：2008.2.1

  Nuclear magnetic resonance spectroscopic methods have been used to characterize the chemical composition of floral nectar of Anigozanthos species with a minimum of sample preparation and without derivatization. The nectar of this passerine-pollinated plant is largely dominated by glucose and fructose, while sucrose occurs only at a minor level. Tyrosine, several additional amino acids, and a variety of carboxylic acids were identified and their concentrations estimated. A linear diarylheptanoid was detected as a trace component, marking the first time this type of secondary product in Hemodoraceae has been found.
• Non-Phenolic Linear Diarylheptanoids from<i>Curcuma xanthorrhiza</i>: A Novel Type of Topical Anti-Inflammatory Agents: Structure-Activity Relationship
  作者：P. Claeson、U. Pongprayoon、T. Sematong、P. Tuchinda、V. Reutrakul、P. Soontornsaratune、W. Taylor

  DOI：10.1055/s-2006-957867

  日期：1996.6

  The topical anti-inflammatory activity of three non-phenolic linear 1,7-diarylheptanoids, previously isolated from a Thai medicinal plant, Curcuma xanthorrhiza (Zingiberaceae) and four new semi-synthetic derivatives of the naturally occurring compounds were assessed in the murine model of ethyl phenylpropiolate-induced ear edema. The naturally occurring compound 1E,3E,1,7-diphenylheptadien-5-one (6) exerted the most potent anti-inflammatory activity, with an ID50 value of similar magnitude to that of the reference drug oxyphenbutazone (67 vs. 46 µg/ear, respectively). None of the semi-synthetic diarylheptanoids was more active than 6. The chemical structures and pharmacological data of the natural and semi-synthetic derivatives identified a distinct structure-activity relationship. The degree of unsaturation in positions 1 and 3, and the nature of the oxygenated functional group in position 5 of the C7-chain were found to play significant roles in determining the observed in vivo activity. Based on these findings, the non-phenolic linear 1,7-diaryl-heptanoids are proposed to represent a novel class of topical anti-inflammatory agents.

  三种非酚类线性1,7-二苯基庚烷酮的局部抗炎活性在小鼠模型中进行了评估，该模型以乙基苯丙酰胺引起的耳部水肿为基础。这些化合物之前是在一种泰国药用植物黄姜（Curcuma xanthorrhiza，姜科）中分离出的，并且还评估了四种新的半合成衍生物。自然存在的化合物1E,3E,1,7-二苯基庚烯-5-酮（6）表现出最强的抗炎活性，其ID50值与参考药物氧苯丁酮相似（分别为67与46 µg/耳）。没有任何半合成的二苯基庚烷酮的活性超过6。天然和半合成衍生物的化学结构和药理数据确立了明显的结构-活性关系。发现C7链中1和3号位的未饱和程度，以及5号位的氧化官能团的性质在决定观察到的体内活性中起着重要作用。基于这些发现，非酚类线性1,7-二苯基庚烷酮被建议代表一种新型的局部抗炎药物类。
• Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids
  作者：Şemsi Betül DEMİR、Hatice SEÇİNTİ、Neslihan ÇELEBİOĞLU、Murat ÖZDAL、Alev SEZEN、Özlem GÜLMEZ、Ömer Faruk ALGUR、Hasan SEÇEN

  DOI：10.3906/kim-1911-61

  日期：——

  Four linear nonphenolic diarylheptanoids were synthesized and their antibacterial activities were studied. (S)-2-Me-CBS-catalysed reduction of alnustone with BH3.SMe2 gave (R) (-)(4E,6E)-1,7-diphenylhepta-4,6-dien-3-ol, a natural product. Reduction of alnustone with Na in t-BuOH at -15 degrees C under NH3 atm gave ( E)-1,7-diphenylhept-5-en-3-one as a Birch-type reduction product. t-BuOK catalysed condensation of benzalacetone with propionyl chloride gave (4Z,6E)-5-hydroxy-1,7-diphenylhepta-4,6-dien-3-one, a natural product. (1E,4Z,6E)-5-Hydroxy-4-phenethyl-1,7-diphenylhepta-1,4,6-trien-3-one, a curcuminoid, was synthesized starting from pentan-2,4-dione in 3 steps. The synthesized chemical compounds were applied against 2 gram-positive bacteria (Bacillus cereus and Arthrobacter agilis), 4 gram-negative bacteria (Pseudomonas aeruginosa, Xanthomonas campestris, Klebsiella oxytoca, and Helicobacter pylori), and 1 yeast (Candida albicans) by the disc diffusion method. All of the synthesized compound exhibited different degrees of antimicrobial activity at concentrations between 20-100 mu g/disc against the test organisms.