(E)-1-(4-hydroxyphenyl)-7-phenylhept-1-en-3-one | 87657-69-0

• 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: (E)-1-(4-hydroxyphenyl)-7-phenylhept-1-en-3-one
• CAS: 87657-69-0
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: SDLPKHSWWKDGFG-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (E)-1-(4-hydroxyphenyl)-7-phenylhept-1-en-3-one 在 palladium on activated charcoal 氢气 作用下， 以 苯 为溶剂， 以73%的产率得到1-(4-hydroxyphenyl)-7-phenyl-3-heptanone
  参考文献：
  名称：

  Synthesis of diarylheptanoids and assessment of their pungency.

  摘要：

  为了将辛辣味与一个苯环上的取代基团联系起来，我们通过克莱森-施密特反应合成了多种药蟾素类似物。通过直接比较味觉实验中获得的阈值浓度来评估它们的辛辣程度。高辛辣度离不开酚羟基的存在，而庚酮部分的 1，2-双键则会降低辛辣度。

  DOI：

  10.1248/cpb.31.2491
• 作为产物：
  描述：

  1-(4-hydroxyphenyl)-7-phenyl-3-heptanone 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 3.0h， 以47%的产率得到(E)-1-(4-hydroxyphenyl)-7-phenylhept-1-en-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

文献信息

• CONNOR, DAVID T.;FLYNN, DANIEL L.
  作者：CONNOR, DAVID T.、FLYNN, DANIEL L.

  DOI：——

  日期：——
• 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.
• Synthesis of diarylheptanoids and assessment of their pungency.
  作者：HIDEJI ITOKAWA、RITSUO AIYAMA、AKIRA IKUTA

  DOI：10.1248/cpb.31.2491

  日期：——

  With the aim of correlating pungency with substituent groups on one benzene ring, various analogues of yakuchinones were synthesized by means of the Claisen-Schmidt reaction. Their pungencies were assessed by direct comparison of the threshold concentrations obtained in taste experiments. The presence of a phenolic hydroxyl group was indispensable for high pungency, while that of a 1, 2-double bond of the heptanone part tended to decrease the pungency.

  为了将辛辣味与一个苯环上的取代基团联系起来，我们通过克莱森-施密特反应合成了多种药蟾素类似物。通过直接比较味觉实验中获得的阈值浓度来评估它们的辛辣程度。高辛辣度离不开酚羟基的存在，而庚酮部分的 1，2-双键则会降低辛辣度。