methyl 2,6-dibromo-3,5-dihydroxybenzoate | 620177-94-8

• 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: methyl 2,6-dibromo-3,5-dihydroxybenzoate
• CAS: 620177-94-8
• 化学式: C₈H₆Br₂O₄
• 分子量: 325.941
• InChiKey: KWPAAHWPKTYGJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,6-dibromo-3,5-dihydroxybenzoate 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 (2-bromo-3,5-bis(methoxymethoxy)phenyl)methanol
  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：

  3,5-二羟基苯甲酸甲酯 在 溴 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 5.5h， 以97%的产率得到methyl 2,6-dibromo-3,5-dihydroxybenzoate
  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

文献信息

• Synthetic analogues of the antibiotic pestalone
  作者：Florian Kaiser、Hans-Günther Schmalz

  DOI：10.1016/s0040-4020(03)01136-0

  日期：2003.9

  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.