1-(4-{[(2E)-3,7-dimethylocta-2,6-dienyl]oxy}-2-hydroxyphenyl)ethanone | 74021-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-{[(2E)-3,7-dimethylocta-2,6-dienyl]oxy}-2-hydroxyphenyl)ethanone
• 英文别名: 2-hydroxyl-4-geranyloxyacetophenone；2-hydroxy-4-geranyloxyacetophenone；1-[4-[(2E)-3,7-dimethylocta-2,6-dienoxy]-2-hydroxyphenyl]ethanone
• CAS: 74021-55-9
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: GCSSIFXYUYGMJU-GXDHUFHOSA-N

物化性质

• 沸点：
  443.3±45.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-{[(2E)-3,7-dimethylocta-2,6-dienyl]oxy}-2-hydroxyphenyl)ethanone 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 2,4-二羟基苯乙酮
  参考文献：
  名称：

  使用三氟化硼醚酯对异戊二烯、香叶基和植基醚和酯进行高效和选择性脱保护的方法

  摘要：

  摘要 开发了一种高效、简单、实用的方法，用于在室温下使用三氟化硼醚合物 (BF3 · OEt2) 对异戊二烯、香叶基和植基醚以及芳香族和脂肪族化合物的酯进行脱保护，首次获得良好的收率。时间。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要

  DOI：

  10.1080/00397911.2011.589561
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 、 香叶基溴 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 1-(4-{[(2E)-3,7-dimethylocta-2,6-dienyl]oxy}-2-hydroxyphenyl)ethanone
  参考文献：
  名称：

  使用三氟化硼醚酯对异戊二烯、香叶基和植基醚和酯进行高效和选择性脱保护的方法

  摘要：

  摘要 开发了一种高效、简单、实用的方法，用于在室温下使用三氟化硼醚合物 (BF3 · OEt2) 对异戊二烯、香叶基和植基醚以及芳香族和脂肪族化合物的酯进行脱保护，首次获得良好的收率。时间。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要

  DOI：

  10.1080/00397911.2011.589561

文献信息

• Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines
  作者：Céline Bruyère、Salvatore Genovese、Benjamin Lallemand、Alexandra Ionescu-Motatu、Massimo Curini、Robert Kiss、Francesco Epifano

  DOI：10.1016/j.bmcl.2011.05.089

  日期：2011.7

  A series of 25 selected oxyprenylated natural phenylpropanoids were synthesized, and their growth inhibitory activities were evaluated in vitro together with 14 other commercially available non-alkylated compounds belonging to the same chemical series. The compounds were tested on six human cancer cell lines using MTT colorimetric assays. The data reveal that of the six chemical groups (G) studied, coumarins (G1), cinnamic and benzoic acids (G2), chalcones (G3), acetophenones (G4), anthraquinones (G5), and cinnamaldehydes and cinnamyl alcohols (G6), G2-related compounds displayed the weakest growth inhibitory activities in vitro, whereas G5-related compounds displayed the highest activities. Quantitative videomicroscopy analyses were then carried out on human U373 glioblastoma cells, which are characterized by various levels of resistance to different pro-apoptotic stimuli. These analyses revealed that compounds 20 (4,2',4'-trihydroxychalcone), and 30 and 31 (two cinnamaldehydes) were cytostatic and able to overcome the intrinsic resistance of U373 cancer cells to pro-apoptotic stimuli. (C) 2011 Elsevier Ltd. All rights reserved.
• First Total Syntheses of 4′-0-Geranylisoliquiritigenin And 4′-O-Geranylnarigenin
  作者：Chusheng Huang、Shuhua Li、Liming Hou、Yulin Li、Ying Li

  DOI：10.1080/00397919908086114

  日期：1999.4

  The title compounds, 4'-O-geranylisoliquiritigenin and 4'-O-geranylnaringenin isolated from Millettia ferruginea and Borania coerulescens respectively, were first synthesized starting from geranyl bromide, 4-hydroxybenzaldehyde and O-hydroxy acetophenones by the condensation reaction and demethoxymethylation as key steps.
• Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents
  作者：Salvatore Genovese、Francesco Epifano、Massimo Curini、Monika Dudra-Jastrzebska、Jarogniew J. Luszczki

  DOI：10.1016/j.bmcl.2009.07.110

  日期：2009.9

  In this study, we synthesized some natural and semi-synthetic prenyloxyphenylpropanoids (e.g., acetophenones, benzoic and cinnamic acids, chalcones, and coumarins), and we assessed their in vivo neuroprotective activity, using the mouse maximal electroshock-induced seizure model (MES test). 7-Iso-pentenyloxycoumarin and (2E)-3-4-[(3-methylbut-2-enyl)oxy]phenyl}prop-2-enoic acid, administered ip at a dose of 300 mg/kg, suppressed MES-induced seizures in mice in a time- and dose-dependent manner. (C) 2009 Elsevier Ltd. All rights reserved.
• Highly Efficient and Selective Deprotection Method for Prenyl, Geranyl, and Phytyl Ethers and Esters Using Borontrifluoride–Etherate
  作者：T. Narender、K. Venkateswarlu、G. Madhur、K. Papi Reddy

  DOI：10.1080/00397911.2011.589561

  日期：2013.1.1

  Abstract An efficient, simple, and practical method has been developed for the deprotection of prenyl, geranyl, and phytyl ethers and esters of aromatic and aliphatic compounds using borontrifluoride–etherate (BF3 · OEt2) at room temperature in good to excellent yields for the first time. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications®

  摘要 开发了一种高效、简单、实用的方法，用于在室温下使用三氟化硼醚合物 (BF3 · OEt2) 对异戊二烯、香叶基和植基醚以及芳香族和脂肪族化合物的酯进行脱保护，首次获得良好的收率。时间。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要