[3,5-bis(methoxymethoxy)-2-(3-methylbut-2-enyl)phenyl][3,5-dichloro-2-methoxy-6-(methoxymethoxy)-4-methylphenyl]methanone | 620177-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [3,5-bis(methoxymethoxy)-2-(3-methylbut-2-enyl)phenyl][3,5-dichloro-2-methoxy-6-(methoxymethoxy)-4-methylphenyl]methanone
• 英文别名: [3,5-bis(methoxymethoxy)-2-(3-methylbut-2-enyl)phenyl]-[3,5-dichloro-2-methoxy-6-(methoxymethoxy)-4-methylphenyl]methanone
• CAS: 620177-98-2
• 化学式: C₂₆H₃₂Cl₂O₈
• 分子量: 543.441
• InChiKey: VIFJVBFWICLVCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.0
• 重原子数：
  36.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [3,5-bis(methoxymethoxy)-2-(3-methylbut-2-enyl)phenyl][3,5-dichloro-2-methoxy-6-(methoxymethoxy)-4-methylphenyl]methanone 在 吡啶 、 甲醇 、 camphor-10-sulfonic acid 作用下， 反应 24.0h， 生成 [3-Acetyloxy-5-(2-acetyloxy-3,5-dichloro-6-methoxy-4-methylbenzoyl)-4-(3-methylbut-2-enyl)phenyl] acetate
  参考文献：
  名称：

  Synthetic analogues of the antibiotic pestalone

  摘要：

  The first synthetic study towards the natural product pestalone (1) is described culminating in the preparation of selected n-1 analogues. Pestalone is a chlorinated and prenylated benzophenone antibiotic, which is of interest due to a strong activity against methicillin-resistant staphylococcus aureus strains (MRSA). Key step of the synthesis is the nucleophilic addition of a highly functionalized aryllithium building block to a 2-prenylated 3,5-dialkoxy-benzaldehyde followed by oxidation. For the introduction of the prenyl sidechain by aryl-allyl coupling, different procedures were evaluated, among them the Stille reaction and a nickel pi-allyl complex coupling. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01136-0
• 作为产物：
  描述：

  methyl 2,6-dibromo-3,5-dihydroxybenzoate 在 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 四丁基氟化铵 、 叔丁基锂 、 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 乙腈 、 正戊烷 为溶剂， 反应 17.5h， 生成 [3,5-bis(methoxymethoxy)-2-(3-methylbut-2-enyl)phenyl][3,5-dichloro-2-methoxy-6-(methoxymethoxy)-4-methylphenyl]methanone
  参考文献：
  名称：

  Synthetic analogues of the antibiotic pestalone

  摘要：

  The first synthetic study towards the natural product pestalone (1) is described culminating in the preparation of selected n-1 analogues. Pestalone is a chlorinated and prenylated benzophenone antibiotic, which is of interest due to a strong activity against methicillin-resistant staphylococcus aureus strains (MRSA). Key step of the synthesis is the nucleophilic addition of a highly functionalized aryllithium building block to a 2-prenylated 3,5-dialkoxy-benzaldehyde followed by oxidation. For the introduction of the prenyl sidechain by aryl-allyl coupling, different procedures were evaluated, among them the Stille reaction and a nickel pi-allyl complex coupling. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01136-0