3-(2,3,6-trimethoxyphenyl)propan-1-ol | 884646-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2,3,6-trimethoxyphenyl)propan-1-ol
• CAS: 884646-71-3
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: CZHFYOMDRSTMNF-UHFFFAOYSA-N

物化性质

• 沸点：
  341.0±37.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,3,6-trimethoxyphenyl)propan-1-ol 在 platinum(IV) oxide 偶氮二甲酸二异丙酯 、 氢气 、 硝酸 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 28.0h， 生成 3-(3-amino-2,5,6-trimethoxy)propyl 5-chloro-2,4-dihydroxybenzoate
  参考文献：
  名称：

  Design, Synthesis, and StructureActivity Relationships for Chimeric Inhibitors of Hsp90

  摘要：

  Inhibition of the 90 kDa heat shock protein (Hsp90) family of molecular chaperones represents a promising new chemotherapeutic approach toward the treatment of several cancers. Previous studies have demonstrated that the natural products, radicicol and geldanamycin, are potent inhibitors of the Hsp90 N-terminal ATP binding site. The cocrystal structures of these molecules bound to Hsp90 have been determined, and through molecular modeling and superimposition of these ligands, hybrids of radicicol and geldanamycin have been designed. A series of macrocylic chimeras of radicicol and geldanamycin and the corresponding seco-agents have been prepared and evaluated for both antiproliferative activity and their ability to induce Hsp90-dependent client protein degradation.

  DOI：

  10.1021/jo061054f
• 作为产物：
  描述：

  1,2,4-三甲氧基苯 在 palladium on activated charcoal 正丁基锂 、 氢气 、 sodium hydride 作用下， 以 乙醚 、 乙酸乙酯 、 甲苯 为溶剂， 反应 29.25h， 生成 3-(2,3,6-trimethoxyphenyl)propan-1-ol
  参考文献：
  名称：

  Design, Synthesis, and StructureActivity Relationships for Chimeric Inhibitors of Hsp90

  摘要：

  Inhibition of the 90 kDa heat shock protein (Hsp90) family of molecular chaperones represents a promising new chemotherapeutic approach toward the treatment of several cancers. Previous studies have demonstrated that the natural products, radicicol and geldanamycin, are potent inhibitors of the Hsp90 N-terminal ATP binding site. The cocrystal structures of these molecules bound to Hsp90 have been determined, and through molecular modeling and superimposition of these ligands, hybrids of radicicol and geldanamycin have been designed. A series of macrocylic chimeras of radicicol and geldanamycin and the corresponding seco-agents have been prepared and evaluated for both antiproliferative activity and their ability to induce Hsp90-dependent client protein degradation.

  DOI：

  10.1021/jo061054f

文献信息

• Heat shock protein 90 inhibitors
  申请人：Blagg Brian

  公开号：US20060089495A1

  公开（公告）日：2006-04-27

  Novel compounds useful for inhibiting the 90 kDa heat shock proteins containing a quinone-like moiety and a di-hydroxy phenol like moiety, similar to geldanamycin and radicicol.

  新型化合物对抑制含有类似醌类结构和二羟基酚类结构的90千道尔顿热休克蛋白具有用途，类似于格尔德霉素和拉迪考尔。
• Molecular Reconstruction with Stereochemical Relay: An Investigation into the Rearrangement of Spiro[4.5]decadienone to Benzoxepane
  作者：Satapanawat Sittihan、Shingo Harada、Tomohiro Isono、Tetsuhiro Nemoto、Somsak Ruchirawat

  DOI：10.1002/asia.202300937

  日期：2024.1.15

  ipso-cyclization to furnish spiro[4.5]decadienones, which rearranged to benzoxepanes upon thermal activation. The stereochemical information was relayed through this high-yielding sequence. Mechanistically, the rearrangement was proposed to proceed via the uncommon ring closure of enoate/quinone oxonium zwitterionic intermediate. Computational studies were conducted to help explain the product distribution

  芳基环氧化物经历酸介导的脱芳香原环化以提供螺[4.5]癸二烯酮，其在热活化后重排为苯并氧杂环己烷。立体化学信息通过这种高产序列传递。从机理上讲，重排被认为是通过烯酸/醌氧鎓两性离子中间体不常见的闭环进行的。进行计算研究以帮助解释产物分布和非对映选择性。
• HEAT SHOCK PROTEIN 90 INHIBITORS
  申请人：Blagg Brian S.J.

  公开号：US20100099865A1

  公开（公告）日：2010-04-22

  Novel compounds useful for inhibiting the 90kDa heat shock proteins containing a quinone-like moiety and a di-hydroxy phenol like moiety, similar to geldanamycin and radicicol.
• US7208630B2
  申请人：——

  公开号：US7208630B2

  公开（公告）日：2007-04-24
• US7605288B2
  申请人：——

  公开号：US7605288B2

  公开（公告）日：2009-10-20