benzyl 3-methoxy-4-benzyloxycinnamate | 481701-70-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: benzyl 3-methoxy-4-benzyloxycinnamate
• 英文别名: benzyl 3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-enoate
• CAS: 481701-70-6
• 化学式: C₂₄H₂₂O₄
• 分子量: 374.436
• InChiKey: XVQBOKOLCJGPRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 3-methoxy-4-benzyloxycinnamate 在 盐酸 、 4-二甲氨基吡啶 、 四氯化钛 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-4-(2-((3-(4-hydroxy-3-methoxyphenyl)acryloyl)oxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  Phenylsulfonylfuroxan NO-donor phenols: Synthesis and multifunctional activities evaluation

  摘要：

  Phenylsulfonyfuroxan nitric oxide (NO)-donor phenols were designed, synthesized and evaluated. The compounds were designed through a symbiotic approach using selected phenols and phenylsulfonylfuroxan NO-donor. The antioxidant activities of the hybrid compounds T-2-T-6 showed to be good in vivo. Compounds T-4 and T-6 revealed excellent yeast alpha-glucosidase inhibitory activity and anti-glycosylation activity. All of the compounds exhibited strong NO releasing activity and significant anti-platelet aggregation activity. The inhibition of platelet aggregation was more than 50% at low concentration (1.5 mu M) and 95% at higher concentration (15 mu M and 150 mu M). The vasodilatation experiment demonstrated that the six compounds under test exhibited definite vasodilation activity (pIC(50) ranged from 5.698 to 6.383), especially compound T6 (pIC(50) was 6.383) which was similar to sodium nitroprusside (pIC(50) was 6.786). Both anticoagulant and vasodilatation effects were correlated with their NO releasing activities. These hybrid phenylsulfonyfuroxan-based NO-donor phenols offer a multifunctional prodrug design concept for the development of therapeutic or preventive agents for metabolic syndrome. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2017.06.023
• 作为产物：
  描述：

  阿魏酸 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以86%的产率得到benzyl 3-methoxy-4-benzyloxycinnamate
  参考文献：
  名称：

  储存和油炸过程中油类的自由基清除活性和新型酚类抗氧化剂的性能

  摘要：

  AbstractNovel phenolic antioxidants: 2a (6′‐hydroxy‐2′,5′,7′,8′‐tetramethylchroman‐2′‐yl)methyl 3‐methoxy‐4‐hydroxycinnamate, 2b (6′‐hydroxy‐2′,5′,7′,8′‐tetramethylchroman‐2′‐yl)methyl 3,5‐dimethoxy‐4‐hydroxycinnamate, 2c (6′‐hydroxy‐2′,5′,7′,8′‐tetramethylchroman‐2′‐yl)methyl 3,4‐dihydroxycinnamate, and 3 (6‐hydroxy‐2,5,7,8‐tetramethylchroman‐2‐yl)methyl (6′‐hydroxy‐2′,5′,7′,8′‐tetramethylchroman‐2′‐carboxylate) have been prepared in good yields and fully characterized by 1H and 13C NMR, and HRMS. Their radical scavenging activities have been evaluated by DPPH and ORAC assays. Each of the synthesized antioxidants exhibited significantly higher radical scavenging activities than trolox and α‐tocopherol. These novel antioxidants efficiently protected canola oil triacylglycerides (CTG) during accelerated storage and frying. Compounds 2c and 3 were significantly more efficient than α‐tocopherol protecting CTG under accelerated storage. All new antioxidants were more efficient than α‐tocopherol under frying conditions and present significantly higher thermal stability.

  DOI：

  10.1007/s11746-011-1889-6