4,6-dibenzyloxy-2-methoxymethyloxybenzaldehyde | 863237-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,6-dibenzyloxy-2-methoxymethyloxybenzaldehyde
• 英文别名: Benzaldehyde, 2-(methoxymethoxy)-4,6-bis(phenylmethoxy)-；2-(methoxymethoxy)-4,6-bis(phenylmethoxy)benzaldehyde
• CAS: 863237-41-6
• 化学式: C₂₃H₂₂O₅
• 分子量: 378.425
• InChiKey: BBTQIRQOPMVYSE-UHFFFAOYSA-N

物化性质

• 沸点：
  557.9±50.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,6-dibenzyloxy-2-methoxymethyloxybenzaldehyde 在 氢氧化钾 、 sodium tetrahydroborate 、 溴 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 (E)-(5-(3-(2,4-bis(benzyloxy)-6-(methoxymethoxy)-phenyl)prop-1-enyl)-1,3-phenylene)bis(oxy)bis(methylene)-dibenzene
  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：

  间苯三酚甲醛 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 4,6-dibenzyloxy-2-methoxymethyloxybenzaldehyde
  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

文献信息

• Total synthesis of tovophyllin B
  作者：Valer Jeso、K.C. Nicolaou

  DOI：10.1016/j.tetlet.2008.12.096

  日期：2009.3

  The first total synthesis of tovophyllin B (2), an antimicrobial xanthone derived from mangosteen. has been accomplished through a convergent strategy from building blocks 6 and 7 involving lithium-mediated coupling, dehydrative cyclization, and 6 pi electrocyclization as key steps. (C) 2008 Elsevier Ltd. All rights reserved.
• Anti-staphylococcal activity and β-lactam resistance attenuating capacity of structural analogues of (−)-epicatechin gallate
  作者：James C. Anderson、Robert A. McCarthy、Sarah Paulin、Peter W. Taylor

  DOI：10.1016/j.bmcl.2011.09.116

  日期：2011.12

  We examined the impact of gradual removal of hydroxyl groups from the A- and B-rings of (-)-epicatechin gallate on antibacterial activity and oxacillin resistance attenuation of an epidemic strain of methicillin resistant Staphylococcus aureus. Removal of both hydroxyls from the B-ring effected a large reduction in oxacillin MIC (from 512 to 0.25 mg/mL at a concentration of 12.5 mg/L); further hydroxyl deletion of the A-ring reduced the oxacillin effect but increased intrinsic anti-staphylococcal activity (C) 2011 Elsevier Ltd. All rights reserved.
• Compounds for use in the treatment of infection
  申请人：Anderson C. James

  公开号：US20070021384A1

  公开（公告）日：2007-01-25

  There is provided a novel compound of the general formula I in which each of R 8 to R 10 is hydrogen, aryl, C 1-6 alkyl, trialkylsilyl or acyl; R 1 to R 5 are individually selected from hydrogen, hydroxy, C 1-6 alkoxy and acyloxy; R 6 and R 7 are H, C 1-4 alkyl, trialkylsilyl or acyl; X is O or NR, and R is H or Me; in which any of the alkyl groups including alkyl groups in alkoxy, acyl and acyloxy groups may be substituted by aryl, C 1-4 alkyl, C 1-4 alkoxy, hydroxyl, trialkylsiloxy or acyloxy groups; with the proviso that R 2 and R 3 are not both OH when R 4 is H or OH, R 1 and R 5 are both H, and X is O. The amide compounds (X is NR) are analogues of epigallocatechin gallate or epicatechin galate, with an amide bond in place of the natural ester bond, with resistance to hydrolysis by esterase enzymes. The ester compounds (X is O) have a different hydroxylation pattern on the B ring as compared to the natural products. The compounds may be used to modulate the resistance to β-lactam antibiotics of various infections, especially methicillin resistant Staphylococcus aureus (MRSA). Pharmaceutical compositions containing the novel compounds and combinations of the novel compounds and β-lactam antibiotics are described.
• US7700646B2
  申请人：——

  公开号：US7700646B2

  公开（公告）日：2010-04-20
• Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus
  作者：James C. Anderson、Catherine Headley、Paul D. Stapleton、Peter W. Taylor

  DOI：10.1016/j.tet.2005.05.086

  日期：2005.8

  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.