3',4,6-tribenzyloxy-2-methoxymethyloxy-E-retrochalcone | 863237-42-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3',4,6-tribenzyloxy-2-methoxymethyloxy-E-retrochalcone
• 英文别名: (E)-3-[2-(methoxymethoxy)-4,6-bis(phenylmethoxy)phenyl]-1-(3-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 863237-42-7
• 化学式: C₃₈H₃₄O₆
• 分子量: 586.684
• InChiKey: IWODGMNWHUWOOD-QZQOTICOSA-N

物化性质

• 熔点：
  108-110 °C
• 沸点：
  756.9±60.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  44.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3',4,6-tribenzyloxy-2-methoxymethyloxy-E-retrochalcone 在 sodium tetrahydroborate 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 1-(3'-benzyloxyphenyl)-3-(2''-methoxymethyloxy-4'',6''-dibenzyloxyphenyl)propan-1-ol
  参考文献：
  名称：

  Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus

  摘要：

  Two enantiomerically pure B-ring modified analogues of (-)epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.086
• 作为产物：
  描述：

  2,4-bis(benzyloxy)-6-hydroxybenzaldehyde 在 氢氧化钾 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 16.0h， 生成 3',4,6-tribenzyloxy-2-methoxymethyloxy-E-retrochalcone
  参考文献：
  名称：

  Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus

  摘要：

  Two enantiomerically pure B-ring modified analogues of (-)epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.086