4-epoxy isoeugenol | 36115-41-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-epoxy isoeugenol
• 英文别名: Oxirane, [[2-methoxy-4-(1-propenyl)phenoxy]methyl]-；2-[(2-methoxy-4-prop-1-enylphenoxy)methyl]oxirane
• CAS: 36115-41-0
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: GRKBETVXAMQRSR-UHFFFAOYSA-N

物化性质

• 熔点：
  59-60 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  346.0±22.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-epoxy isoeugenol 在 Oxone 、 四丁基硫酸氢铵 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 3.0h， 以92%的产率得到
  参考文献：
  名称：

  Diglycidylether of iso-eugenol: a suitable lignin-derived synthon for epoxy thermoset applications

  摘要：

  从木质素中催化裂解出的Iso-eugenol (isoEu)被转化为Iso-eugenol的二缩醛(DGE-isoEu)，在酸酐基固化剂的存在下，可以得到新的生物基环氧树脂热固性材料。

  DOI：

  10.1039/c6ra15200g
• 作为产物：
  描述：

  异丁香酚 、 环氧氯丙烷 在 potassium carbonate 作用下， 反应 20.0h， 生成 4-epoxy isoeugenol
  参考文献：
  名称：

  NaOH/BEt3 催化环氧化物区域选择性硼氢化制仲醇

  摘要：

  这里描述了环氧化物高效和区域选择性的硼氢化成仲醇，该反应由组合的 NaOH/BEt 3催化剂催化。这种不含过渡金属的催化体系适用于许多卤代化合物，并且在温和条件下对烯烃基团具有良好的耐受性。

  DOI：

  10.1002/ejoc.202200759

文献信息

• KMST isoeugenol derivatives and pharmaceutical activity
  申请人：——

  公开号：US20040266785A1

  公开（公告）日：2004-12-30

  A compound having the following formula I: 1 where R 1 is alkyl group or alkenyl group, X represents 2 R 2 is selected from the group consisting of a halogen (o, m, p) group such as F, Cl, Br or I, —NH 2 , —NO 2 and a hydrogen group, R 3 is a hydrogen group or OH, and n is 0 to 2. The compound has pharmacologically &agr; 2 -adrenergic/5-HT 2A antagonist activity, 5-HT re-uptake activity, and anti-oxidant activity. The compound is produced by preparing 4-epoxy isoeugenol, mixing piperazine dissolved in methanol with the 4-epoxy isoeugenol to reflux at 100° C. for approximately 2 to approximately 6 hours, removing the methanol, passing the mixture through a silica gel column chromatography after the removing step, eluting the passed mixture with n-hexane and ethyl acetate, drying the eluted mixture, and crystallizing the dried mixture with methanol.

  具有以下化学式I的化合物：其中R1是烷基或烯基基团，X代表R2从卤素（o，m，p）基团（如F、Cl、Br或I）、—NH2、—NO2和氢基团中选择，R3是氢基团或OH，n为0至2。该化合物具有药理学α2-肾上腺素/5-HT2A拮抗活性、5-HT再摄取活性和抗氧化活性。该化合物通过制备4-环氧异丁基酚，将丙二胺溶解在甲醇中与4-环氧异丁基酚混合，在100°C回流约2至约6小时，去除甲醇，经过去除步骤后通过硅胶柱色谱法将混合物通过，用正己烷和乙酸乙酯洗脱通过的混合物，干燥洗脱的混合物，并用甲醇结晶干燥的混合物。
• Compound eugenosedin-a and antidepressants protect against lipopolysaccharide-induced shock
  申请人：——

  公开号：US20040266786A1

  公开（公告）日：2004-12-30

  Isoeugenol derivative compounds having the moiety 1 and which exhibit &agr; 2 -adrenergic/5-HT 2A antagonist, 5-HT re-uptake inhibition, and anti-oxidant activities.

  具有1部分的异丁香酚衍生化合物表现出α2-肾上腺素能/5-HT2A拮抗剂、5-HT再摄取抑制和抗氧化活性。
• A new aspect of view in synthesizing new type β-adrenoceptor blockers with ancillary antioxidant activities
  作者：Yeun-Chih Huang、Bin-Nan Wu、Jwu-Lai Yeh、Sheue-Jiun Chen、Jyh-Chong Liang、Yi-Ching Lo、Ing-Jun Chen

  DOI：10.1016/s0968-0896(01)00067-0

  日期：2001.7

  A series of vanilloid-type beta -adrenoceptor blockers derived from antioxidant traditional Chinese herbal medicines were synthesized and tested for their antioxidant and adrenoceptor antagonistic activities. They all possessed significant beta -adrenoceptor blocking activities under in vitro experiments and radioligand binding assays. In addition, some compounds were further examined in in vivo tests and produced antagonist effects matching that of propranolol and labetalol by measurements of antagonism coward (-) isoproterenol-induced tachycardia and (-)phenylephrine-induced presser responses in anesthetized rats. Furthermore. all of the compounds had antioxidant effects inherited from their original structures. In conclusion. compound 11 had the most potent beta -adrenoceptors blocking activity. 12 and 13 possessed high cardioselectivity, whereas 14, 15 and 16 possessed additional alpha -adrenoceptor blocking activity and 15 is the most effective antioxidant of all. The antioxidant activity may be due to their alpha and beta unsaturated side chain at position 1 and ortho-substituted methoxy moiety on 4-phenoxyethylamine. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Diglycidylether of iso-eugenol: a suitable lignin-derived synthon for epoxy thermoset applications
  作者：Camille François、Sylvie Pourchet、Gilles Boni、Stéphane Fontaine、Yves Gaillard、Vincent Placet、Maxim V. Galkin、Alexander Orebom、Joseph Samec、Laurent Plasseraud

  DOI：10.1039/c6ra15200g

  日期：——

  Iso-eugenol (isoEu), catalytically fragmented from lignin, is converted into a diglycidylether of iso-eugenol (DGE-isoEu) which leads in the presence of anhydride acids based hardeners to new biobased epoxy thermosets.

  从木质素中催化裂解出的Iso-eugenol (isoEu)被转化为Iso-eugenol的二缩醛(DGE-isoEu)，在酸酐基固化剂的存在下，可以得到新的生物基环氧树脂热固性材料。
• NaOH/BEt ₃ Catalyzed Regioselective Hydroboration of Epoxides to Secondary Alcohols
  作者：Jiali Wang、Wubin Yao、Dandan Hu、Xinxin Qi、Jun‐Qi Zhang、Hongjun Ren

  DOI：10.1002/ejoc.202200759

  日期：2022.9.20

  Here described an efficient and regioselective hydroboration of epoxides to secondary alcohols, the reaction is catalyzed by a combined NaOH/BEt3 catalyst. Such a transition-metal-free catalytic system is suitable for many halogenated compounds and well-tolerated to olefin group under mild conditions.

  这里描述了环氧化物高效和区域选择性的硼氢化成仲醇，该反应由组合的 NaOH/BEt 3催化剂催化。这种不含过渡金属的催化体系适用于许多卤代化合物，并且在温和条件下对烯烃基团具有良好的耐受性。