ο-Benzoyloxy-phloracetophenon | 130471-75-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: ο-Benzoyloxy-phloracetophenon
• 英文别名: 4-O-benzoylphloracetophenone；1-(4-benzoyloxy-2,6-dihydroxy-phenyl)-ethanone；1-(4-Benzoyloxy-2,6-dihydroxy-phenyl)-aethanon；2.6-Dioxy-4-benzoyloxy-acetophenon；Ethanone, 1-[4-(benzoyloxy)-2,6-dihydroxyphenyl]-；(4-acetyl-3,5-dihydroxyphenyl) benzoate
• CAS: 130471-75-9
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: ZLVNHCPQFPPBFU-UHFFFAOYSA-N

物化性质

• 熔点：
  210–211°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ο-Benzoyloxy-phloracetophenon 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 氰化汞 作用下， 以 甲醇 、 硝基甲烷 、 乙醇 为溶剂， 反应 1.0h， 生成 2',4,4'-6'-Tetrahydroxydihydrochalcone 2'-O-α-D-mannopyranoside
  参考文献：
  名称：

  Esaki, Sachiko; Abe, Manami; Shiba, Naoko, Agricultural and Biological Chemistry, 1990, vol. 54, # 6, p. 1583 - 1585

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 、 苯甲酰氯 在 氢氧化钾 作用下， 以 水 为溶剂， 以40%的产率得到ο-Benzoyloxy-phloracetophenon
  参考文献：
  名称：

  Synthesis and biological evaluation of phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors

  摘要：

  Nucleoside transporter inhibitors have potential therapeutic applications as anticancer, antiviral, cardio-protective and neuroprotective agents. Although quite a few potent inhibitors of the equilibrative nucleoside transporters are known, largely missing are the concentrative nucleoside transporter inhibitors. Phloridzin (3, K-i = 16.00 mu M) is a known moderate inhibitor of the concentrative nucleoside transporters. We have synthesized and evaluated analogs of phloridzin at the hCNT3 nucleoside transporter. Within the series of synthesized analogs compound 16 (K-i = 2.88 mu M), possessing a ribofuranose sugar unit instead of a glucopyranose as present in phloridzin, exhibited the highest binding affinity at the hCNT3 transporter. Phloridzin and compound 16 have also been shown to be selective for the hCNT3 transporter as compared with the hENT1 transporter. Compound 16 can serve as a new lead which after further modi. cations could yield selective and potent hCNT3 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.112

文献信息

• Struktur und synthese von flavonol-triosiden aus rhamnus-arten
  作者：Ingrid Riess-Maurer、Hildebert Wagner

  DOI：10.1016/0040-4020(82)85113-2

  日期：1982.1

  By synthesis and 13C-NMR spectroscopic investigations of rhamnocitrin-, rhamnazin- and rhamnetin - 3 - O - [O - α - l - rhamnopyranosyl - (1 → 4) - O - α - l - rhamnopyranosyl - (1 → 6)] β - d - galactopyranosides and of rhamnocitrin - 3 - O - [O - α - l - rhamnopyranosyl - (1 → 3) - O - α - l - rhamnopyranosyl - (1 → 6)] - β - d - galactopyranoside (rhamnocitrin - 3 - O - β - rhamnisoide) it was proved

  通过鼠李糖苷，鼠李糖苷和鼠李糖苷-3-O-[O-α-l-鼠李吡喃糖基-（1→4）-O-α-l-鼠李糖吡喃糖基-（1→6）的合成和13 C-NMR光谱研究]β-d-半乳糖吡喃糖苷和鼠李糖苷-3-O-[O-α-l-鼠李糖吡喃糖基-（1→3）-O-α-l-鼠李糖吡喃糖基-（1→6）]-β-d-半乳糖吡喃糖苷（鼠李糖苷-3-O-β-鼠李糖苷）被证明，到目前为止，从不同鼠李属物种中分离出的所有天然黄酮三糖苷均含有糖基鼠李糖。因此表明，黄连素（鼠李糖苷-3-O-β-鼠李糖苷）与alaternin和黄原素A（鼠李素-3-O-β-鼠李糖苷）与黄原素B是相同的，而黄花色素C是鼠李糖苷-3- O-β -鼠李糖苷。从Rhamnus saxatilis JACQ。，ssp。萨克斯 分离出新的黄酮醇-乙酰基-三醇苷，并通过MS和13 C-NMR光谱法鉴定其结构为鼠李糖苷-3-O-[O-α-l-鼠李糖吡喃糖基-（1→3）-O-（4
• Canter et al., Journal of the Chemical Society, 1931, p. 1255,1264
  作者：Canter et al.

  DOI：——

  日期：——
• Zemplen; Bognar, Chemische Berichte, 1942, vol. 75, p. 1040,1041
  作者：Zemplen、Bognar

  DOI：——

  日期：——
• Sonn; Buelow, Chemische Berichte, 1925, vol. 58, p. 1697
  作者：Sonn、Buelow

  DOI：——

  日期：——
• Esaki, Sachiko; Goda, Toshinao; Takase, Sachiko, Agricultural and Biological Chemistry, 1991, vol. 55, # 11, p. 2855 - 2860
  作者：Esaki, Sachiko、Goda, Toshinao、Takase, Sachiko、Sugiyama, Naoko、Kamiya, Shintaro

  DOI：——

  日期：——