(7-hydroxy-2,2-dimethylchroman-5-yl)(3,5-dichloro-2-hydroxy-6-methoxy-4-methylphenyl)methanone

• 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: (7-hydroxy-2,2-dimethylchroman-5-yl)(3,5-dichloro-2-hydroxy-6-methoxy-4-methylphenyl)methanone
• 英文别名: (3,5-Dichloro-2-hydroxy-6-methoxy-4-methylphenyl)-(7-hydroxy-2,2-dimethyl-3,4-dihydrochromen-5-yl)methanone
• 化学式: C₂₀H₂₀Cl₂O₅
• 分子量: 411.282
• InChiKey: CNLUBCVCVWNNDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,5-二羟基苯甲酸甲酯 在 tris(dibenzylideneacetone)dipalladium (0) 甲醇 、 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 三叔丁基膦 、 溴 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 31.75h， 生成 (7-hydroxy-2,2-dimethylchroman-5-yl)(3,5-dichloro-2-hydroxy-6-methoxy-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

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.