diethyl (3,5-bis(benzyloxy)-4-methylbenzyl)phosphonate | 1006685-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl (3,5-bis(benzyloxy)-4-methylbenzyl)phosphonate
• CAS: 1006685-29-5
• 化学式: C₂₆H₃₁O₅P
• 分子量: 454.503
• InChiKey: CEQVQIAVCWSVRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.92
• 重原子数：
  32.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-苄氧基苯甲醛 、 diethyl (3,5-bis(benzyloxy)-4-methylbenzyl)phosphonate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 以75.7%的产率得到(E)-1,3-bis(benzyloxy)-5-[4-(benzyloxy)styryl]-2-methylbenzene
  参考文献：
  名称：

  Effect of Methyl Substitution on the Antioxidative Property and Genotoxicity of Resveratrol

  摘要：

  Resveratrol (trans- 3,4 ',5-trihydroxystilbene) is a natural phytoalexin with various biological activities including inhibition of lipid peroxidation and free radical scavenging properties. In addition to its beneficial effects, resveratrol also has significant genotoxicity that leads to a high frequency of chromosome aberration together with micronucleus and sister chromatid exchanges. To enhance the radical scavenging activities and to reduce the genotoxicity of resveratrol, we designed 4 '-methyl resveratrol analogues where a methyl group was introduced at the ortho position relative to the 4 '-hydroxy group, which is responsible for both antioxidative activities and genotoxicity of resveratrol. These synthesized methyl analogues of resveratrol showed increased antioxidative activities against galvinoxyl radical as an oxyl radical species. Furthermore, the methyl analogues also surprisingly showed reduced in vitro genotoxicities, suggesting that methyl substitution may improve resveratrol efficacy.

  DOI：

  10.1021/tx7003008
• 作为产物：
  描述：

  3,5-bis(benzyloxy)-4-methylbenzyl bromide 、 亚磷酸三乙酯 在 四丁基碘化铵 作用下， 反应 12.0h， 以95%的产率得到diethyl (3,5-bis(benzyloxy)-4-methylbenzyl)phosphonate
  参考文献：
  名称：

  Effect of Methyl Substitution on the Antioxidative Property and Genotoxicity of Resveratrol

  摘要：

  Resveratrol (trans- 3,4 ',5-trihydroxystilbene) is a natural phytoalexin with various biological activities including inhibition of lipid peroxidation and free radical scavenging properties. In addition to its beneficial effects, resveratrol also has significant genotoxicity that leads to a high frequency of chromosome aberration together with micronucleus and sister chromatid exchanges. To enhance the radical scavenging activities and to reduce the genotoxicity of resveratrol, we designed 4 '-methyl resveratrol analogues where a methyl group was introduced at the ortho position relative to the 4 '-hydroxy group, which is responsible for both antioxidative activities and genotoxicity of resveratrol. These synthesized methyl analogues of resveratrol showed increased antioxidative activities against galvinoxyl radical as an oxyl radical species. Furthermore, the methyl analogues also surprisingly showed reduced in vitro genotoxicities, suggesting that methyl substitution may improve resveratrol efficacy.

  DOI：

  10.1021/tx7003008