(E)-1,7-diphenyl-hept-6-en-3-one | 87030-31-7

• 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)-1,7-diphenyl-hept-6-en-3-one
• 英文别名: 1,7-diphenyl-(6E)-6-hepten-3-one；(E)-1,7-diphenylhept-6-en-3-one
• CAS: 87030-31-7
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: VNFWNGSEJXPCSW-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1,7-diphenyl-hept-6-en-3-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以95%的产率得到1,7-二苯基-3-庚酮
  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：

  3-苯丙酸乙酯 在 氢氧化钾 、 正丁基锂 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.5h， 生成 (E)-1,7-diphenyl-hept-6-en-3-one
  参考文献：
  名称：

  Diphenylphosphinoyl-mediated synthesis of ketones

  摘要：

  α-二苯基膦酰基酮在α位上选择性且顺序性地进行烷基化。双锂化和选择性烷基化发生在较不稳定的γ位。脱膦酰化得到的烷基化产物是酮。单烷基化具有选择性，形成的中间体晶体高度结晶，且可以进行一步完成的方法。该方法非常适合制备酸敏感的酮。

  DOI：

  10.1039/b606873a

文献信息

• Ti(O<i>i</i>Pr)₄-Enabled Dual Photoredox and Nickel-Catalyzed Arylation and Alkenylation of Cyclopropanols
  作者：Nastassia Varabyeva、Maryia Barysevich、Yauhen Aniskevich、Alaksiej Hurski

  DOI：10.1021/acs.orglett.1c01795

  日期：2021.7.16

  Readily available from esters or ketones, cyclopropanols are inclined to undergo diverse ring-opening transformations. Their one-electron oxidation is a conventional way to β-carbonyl radicals. However, despite this fact, their application as a coupling partner in dual photoredox and nickel-catalyzed reactions with organic halides remains underdeveloped. Here, we report that the Ti(OiPr)4 additive

  环丙醇很容易从酯或酮中获得，倾向于进行各种开环转化。它们的单电子氧化是β-羰基自由基的常规方式。然而，尽管如此，它们作为偶联伙伴在与有机卤化物的双重光氧化还原和镍催化反应中的应用仍然不成熟。在这里，我们报告了 Ti(O i Pr) 4添加剂使这种难以捉摸的与芳基溴和烯基溴的交叉偶联成为可能，从而产生 β 取代的酮。
• 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。
• Discovery of diarylheptanoids that activate α7 nAchR-JAK2-STAT3 signaling in macrophages with anti-inflammatory activity in vitro and in vivo
  作者：Yuan Lin、Kanjana Wongkrajang、Xiaofei Shen、Ping Wang、Zongyuan Zhou、Thipphawan Chuprajob、Nilubon Sornkaew、Na Yang、Lijuan Yang、Xiaoxia Lu、Ratchanaporn Chokchaisiri、Apichart Suksamrarn、Guolin Zhang、Fei Wang

  DOI：10.1016/j.bmc.2022.116811

  日期：2022.7

  anti-inflammatory properties. However, the possible mechanism of diarylheptanoids has rarely been investigated. In this study, we isolated and synthesized 49 diarylheptanoids and analogues and evaluated their anti-inflammatory activities. Among them, compounds 28 and 40 markedly blocked lipopolysaccharide (LPS)-induced production of nitric oxide (NO), interleukin-1β (IL-1β) and interleukin-6 in murine RAW264.7 cells

  脓毒症等急性炎症性疾病是危及生命的疾病。调节 α7 烟碱型乙酰胆碱受体 (α7 nAchR) 介导的信号传导可能是治疗败血症的有希望的策略。早就发现二芳基庚烷具有抗炎特性。然而，很少研究二芳基庚烷的可能机制。在这项研究中，我们分离并合成了 49 种二芳基庚烷和类似物，并评估了它们的抗炎活性。其中，化合物28和40显着阻断了脂多糖 (LPS) 诱导的小鼠 RAW264.7 细胞中一氧化氮 (NO)、白细胞介素 1β (IL-1β) 和白细胞介素 6 的产生。此外，化合物28和40还有效减弱 LPS 诱导的脓毒症、急性肺损伤和体内细胞因子释放。从机制上讲，化合物28和40显着诱导 janus 激酶 2/信号转导和转录激活因子 3 (JAK2/STAT3) 信号传导和核因子-κB (NF-κB) 通路的抑制。此外，阻断 α7 nAchR 可以有效地消除化合物28和40介导的 JAK2-STAT3
• Substituted pyrrolidine cardiovascular system regulators and antihypertensives, their preparation and use
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0071399A2

  公开（公告）日：1983-02-09

  Compounds of the formula: and the pharmaceutically acceptable acid addition salts thereof, wherein: each X is indeoendently selected from -F, -R1, -OR. -S(O)dR', -CONHR, -NHR, -CH2OR, -CN, -NHCONHR, -NHCSNHR, -NHCOR', -SO2NHR, -NHSO2R1, and -NHCO2R wherein R is either hydrogen or lower alkyl wherein lower alkyl is defined as a straight or branched hydrocarbon chain of 1-4 carbon atoms, R' is lower alkyl wherein alkyl is as defined above and d is 0, 1, or 2, or two Xs taken together are -OCH2O-; each Y is independently selected from the same group as set forth for X; B is hydrogen or hydroxyl; a is 0, 1, or 2; b is 0, 1, or 2; c is 0, 1, 2 or 3; are useful as regulators of the cardiovascular system and are also bronchodilators.

  式化合物 及其药学上可接受的酸加成盐，其中 每个 X 不可重复地选自 -F、-R1、-OR.-S(O)dR'、-CONHR、-NHR、-CH2OR、-CN、-NHCONHR、-NHCSNHR、-NHCOR'、-SO2NHR、-NHSO2R1 和 -NHCO2R，其中 R 是氢或低级烷基，其中低级烷基定义为 1-4 个碳原子的直链或支链烃链，R'是低级烷基，其中烷基定义如上，d 是 0、1 或 2，或两个 X 合在一起是 -OCH2O-； 每个 Y 独立地选自与 X 相同的组； B 是氢或羟基； a 是 0、1 或 2 b 是 0、1 或 2 c 是 0、1、2 或 3；可作为心血管系统的调节剂，也是支气管扩张剂。
• Diphenylphosphinoyl-mediated synthesis of ketones
  作者：David J. Fox、Daniel Sejer Pedersen、Stuart Warren

  DOI：10.1039/b606873a

  日期：——

  α-Diphenylphosphinoyl ketones are selectively and sequentially alkylated at the α-position. Double lithiation and selective alkylation occurs at the less stabilised γ-position. Dephosphinoylation of the alkylation products gives ketones. Mono-alkylation is selective, highly crystalline intermediates are formed and a one-pot strategy is possible. The method is ideally suited for the preparation of acid-sensitive ketones.

  α-二苯基膦酰基酮在α位上选择性且顺序性地进行烷基化。双锂化和选择性烷基化发生在较不稳定的γ位。脱膦酰化得到的烷基化产物是酮。单烷基化具有选择性，形成的中间体晶体高度结晶，且可以进行一步完成的方法。该方法非常适合制备酸敏感的酮。