(4E,6E)-1-(4-hydroxyphenyl)-7-phenylhepta-4,6-dien-3-one | 562810-28-0

• 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: (4E,6E)-1-(4-hydroxyphenyl)-7-phenylhepta-4,6-dien-3-one
• 英文别名: 1-(4-hydroxyphenyl)-7-phenyl-(4E,6E)-4,6-heptadien-3-one
• CAS: 562810-28-0
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: GIXGHUAQPPUMRA-KBXRYBNXSA-N

物化性质

• 熔点：
  129.3-130.0 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  498.7±38.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4E,6E)-1-(4-hydroxyphenyl)-7-phenylhepta-4,6-dien-3-one 、 碘甲烷 在 吡啶 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以82%的产率得到(4E,6E)-1-(4-methoxyphenyl)-7-phenylhepta-4,6-dien-3-one
  参考文献：
  名称：

  Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation

  摘要：

  Three new diarylheptanoids, a 1: 2 mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-( 6E)-6-hepten-3- one ( 15), together with two synthetically known diarylheptanoids 1,7-diphenyl-(1E,3E,5E)-1,3,5-triene(9) and 1-(4-hydroxyphenyl)7-phenyl-(4E,6E)-4,6-heptadien-3- one ( 16), and nine known diarylheptanoids, 2, 8, 10 - 12, 14, a 3: 1 mixture of 17a and 17b, and 18, were isolated from the rhizomes of Curcuma comosa Roxb. The absolute stereochemistry of the isolated compounds has also been determined using the modified Mosher's method. The isolated compounds and the chemically modified analogues were evaluated for their estrogenic-like transcriptional activity using RT-PCR in HeLa cell line. Some of the isolated diarylheptanoids and their modified analogues exhibited estrogenic activity comparable to or higher than that of the phytoestrogen genistein. Based on the transcriptional activation of both estrogenic targets, Bcl-xL and ER beta gene expression, the structural features for a diarylheptanoid to exhibit high estrogenic activity are the presence of an phenolic function conjugated with the aromatic ring at the 7-position, a keto group at the 3-position, and a phenolic hydroxyl group at the p-position of the aromatic ring attached to the 1- position of the heptyl chain. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.051
• 作为产物：
  描述：

  4-(3-氧代丁基)苯基苯甲酸酯 在 4 A molecular sieve 、 potassium carbonate 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 1.25h， 生成 (4E,6E)-1-(4-hydroxyphenyl)-7-phenylhepta-4,6-dien-3-one
  参考文献：
  名称：

  通过三种不同的策略合成新的生物合成重要的二芳基庚烷及其氧杂和氟类似物

  摘要：

  摘要 Wittig、aldol 和 Wittig-Horner 反应已被用于合成新的二芳基庚烷类化合物，它们是植物中苯菲酮生物合成的假定中间体。与其他方法相比，Wittig-Horner 方法是最合适的，并且产生了显着更高的产量。

  DOI：

  10.1081/scc-120016367

文献信息

• Synthesis of New Biosynthetically Important Diarylheptanoids and Their Oxa- and Fluoro- Analogues by Three Different Strategies
  作者：Alexander Baranovsky、Bettina Schmitt、Daniel J. Fowler、Bernd Schneider

  DOI：10.1081/scc-120016367

  日期：2003.1.4

  Abstract Wittig, aldol and Wittig-Horner reactions have been used to synthesize new diarylheptanoids, which are putative intermediates in phenylphenalenone biosynthesis in plants. The Wittig-Horner approach was most suitable and gave significantly higher yields in comparison with other methods.

  摘要 Wittig、aldol 和 Wittig-Horner 反应已被用于合成新的二芳基庚烷类化合物，它们是植物中苯菲酮生物合成的假定中间体。与其他方法相比，Wittig-Horner 方法是最合适的，并且产生了显着更高的产量。
• Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation
  作者：Apichart Suksamrarn、Mathurose Ponglikitmongkol、Kanjana Wongkrajang、Anon Chindaduang、Suthadta Kittidanairak、Aroon Jankam、Boon-ek Yingyongnarongkul、Narin Kittipanumat、Ratchanaporn Chokchaisiri、Pichit Khetkam、Pawinee Piyachaturawat

  DOI：10.1016/j.bmc.2008.05.051

  日期：2008.7

  Three new diarylheptanoids, a 1: 2 mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-( 6E)-6-hepten-3- one ( 15), together with two synthetically known diarylheptanoids 1,7-diphenyl-(1E,3E,5E)-1,3,5-triene(9) and 1-(4-hydroxyphenyl)7-phenyl-(4E,6E)-4,6-heptadien-3- one ( 16), and nine known diarylheptanoids, 2, 8, 10 - 12, 14, a 3: 1 mixture of 17a and 17b, and 18, were isolated from the rhizomes of Curcuma comosa Roxb. The absolute stereochemistry of the isolated compounds has also been determined using the modified Mosher's method. The isolated compounds and the chemically modified analogues were evaluated for their estrogenic-like transcriptional activity using RT-PCR in HeLa cell line. Some of the isolated diarylheptanoids and their modified analogues exhibited estrogenic activity comparable to or higher than that of the phytoestrogen genistein. Based on the transcriptional activation of both estrogenic targets, Bcl-xL and ER beta gene expression, the structural features for a diarylheptanoid to exhibit high estrogenic activity are the presence of an phenolic function conjugated with the aromatic ring at the 7-position, a keto group at the 3-position, and a phenolic hydroxyl group at the p-position of the aromatic ring attached to the 1- position of the heptyl chain. (c) 2008 Elsevier Ltd. All rights reserved.

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