(E)-1,3-dimethoxy-5-(non-1-enyl)benzene | 634922-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1,3-dimethoxy-5-(non-1-enyl)benzene
• 英文别名: 1,3-dimethoxy-5-[(E)-non-1-enyl]benzene
• CAS: 634922-45-5
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: VWRLPWDGPZQUOU-ZHACJKMWSA-N

物化性质

• 沸点：
  373.4±22.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1,3-dimethoxy-5-(non-1-enyl)benzene 在 palladium on activated charcoal chromium(VI) oxide 、 lithium aluminium tetrahydride 、 硫酸 、 水 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 78.0h， 生成 2-acetoxy-5-methoxy-3-(non-1-yl)benzo-1,4-quinone
  参考文献：
  名称：

  取代对苯醌的合成及药害评价

  摘要：

  Sorgoleone (1) 是高粱根系分泌物的主要成分之一。Sorgoleone 是一种化感化学物质，可减少阔叶植物的生长。3,5-二甲氧基苯甲醇 (3) 用作合成 2-甲氧基-6-(非-1-基)苯并-1,4-醌 (9) 的原料，产率为 69%。(9)用乙酸酐乙酰化得到三乙酸酯(10)，产率为82％。然后将三乙酸酯 (10) 分两步转化为 2-羟基-5-甲氧基-3-(非-1-基)苯并-1,4-醌 (11) 和 2-乙酰氧基-5-甲氧基-3- (non-1-yl)benzo-1,4-quinone (12)，产率分别为 8% 和 37%。还通过(12)与DBU反应得到醌(11)，产率为63％。(3) 的烷基化和用铬酸酐氧化形成新的醌 (16) (17) 和 (18)，总产率分别为 23%、16% 和 12%。

  DOI：

  10.1071/ch02032
• 作为产物：
  描述：

  1-溴辛烷 在 potassium carbonate 、 三苯基膦 作用下， 以 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 24.0h， 生成 (Z)-1,3-dimethoxy-5-(non-1-enyl)benzene 、 (E)-1,3-dimethoxy-5-(non-1-enyl)benzene
  参考文献：
  名称：

  COMPOUNDS HAVING AGONISTIC EFFECT AGAINST GPR84, PREPARATION METHOD FOR COMPOUNDS AND USE OF COMPOUNDS

  摘要：

  本发明涉及一类由式I表示的化合物，或其药用可接受盐，其制备方法，以及作为GPR84激动剂的小分子工具的应用，以及它们在制备治疗败血症的药物中的应用。

  公开号：

  US20180237399A1

文献信息

• An expedient synthesis of 5-<i>n</i>-alkylresorcinols and novel 5-<i>n</i>-alkylresorcinol haptens
  作者：Kirsti Parikka、Kristiina Wähälä

  DOI：10.3762/bjoc.5.22

  日期：——

  The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C₂₃ and C₂₅ analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semi-stabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.

  描述了通过一种新颖的Wittig反应改进合成生物活性长烷基链5-烷基间苯二酚，这种物质存在于全谷物产品中。合成了黑麦和小麦中所有主要的长链5-烷基间苯二酚，包括C23和C25类似物以及以前未制备的半抗原。在水中，半稳定叶立德和烷醛的微波促进反应在加压和开放系统中均获得良好产率。另一种微波促进合成方法是从非稳定的烷基三苯基膦盐和3,5-二甲氧基苯甲醛出发。即使起始材料在水中不溶解，水介质也适用于这些反应。5-烷基间苯二酚是全谷物摄入的潜在生物标志物，而新的5-烷基间苯二酚半抗原衍生物将为烷基间苯二酚的免疫化学检测技术打开道路。
• Synthesis and Inhibitory Activities against Colon Cancer Cell Growth and Proteasome of Alkylresorcinols
  作者：Yingdong Zhu、Dominique N. Soroka、Shengmin Sang

  DOI：10.1021/jf302872a

  日期：2012.9.5

  We have identified alkylresorcinols (ARs) as the major active components in wheat bran against human colon cancer cell growth (HCT-116 and HT-29) using a bioassay-guided approach. To further study the structure activity relationships, 15 ARs and their intermediates (1-15) were synthesized expediently by the modified Wittig reaction in aqueous media, and six 5-alkylpyrogallols and their analogues (16-21) were prepared by the general Grignard reaction. The synthetic AR analogues were evaluated for activities against the growth of human colon cancer cells HCT-116 and HT-29 and the chymotrypsin-like activity of the human 20S proteasome. Our results found that (1) AR C13:0 and C15:0 (13 and 14) had the greatest inhibitory effects in human colon cancer cells HCT-116 and HT-29, while decreasing or increasing the side chain lengths diminished the activities; (2) two free meta-hydroxyl groups at C-1 and C-3 on the aromatic ring of the AR analogues greatly contributed to their antitumor activity; (3) the introduction of a third hydroxyl group at C-2 (20 and 21) into the aromatic ring of the AR analogues yielded no significant enhancement in activity against HCT-116 cells and decimated the effects against HT-29 cells, but dramatically increased the activity against the chymotrypsin-like activity of the human 20S proteasome; and (4) AR C11:0 (12) was found to have the greatest effect in a series of AR C9:0-C17:0 against the chymotrypsin-like activity of the human 20S proteasome.