2-acetyl-1-hydroxy-8-methoxy-3-methylnaphthalene | 92190-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-acetyl-1-hydroxy-8-methoxy-3-methylnaphthalene
• 英文别名: 2-acetyl-8-methoxy-3-methyl-1-naphthol；1-(1-hydroxy-8-methoxy-3-methylnaphthalen-2-yl)ethanone；8-O-Methyl-musizin；Ethanone, 1-(1-hydroxy-8-methoxy-3-methyl-2-naphthalenyl)-
• CAS: 92190-16-4
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: VSFUBAXYDFGXOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetyl-1-hydroxy-8-methoxy-3-methylnaphthalene 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 以85%的产率得到羊蹄素
  参考文献：
  名称：

  Rizzacasa, Mark A.; Sargent, Melvyn V., Australian Journal of Chemistry, 1988, vol. 41, # 7, p. 1087 - 1097

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(乙酰基氧基)-5-甲氧基-2-萘羧酸甲酯 在 palladium on activated charcoal 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 26.0h， 生成 2-acetyl-1-hydroxy-8-methoxy-3-methylnaphthalene
  参考文献：
  名称：

  Rizzacasa, Mark A.; Sargent, Melvyn V., Australian Journal of Chemistry, 1988, vol. 41, # 7, p. 1087 - 1097

  摘要：

  DOI：

文献信息

• Constituents of <i>Eremurus chinensis</i>
  作者：Chong Li、Jian-Gong Shi、Ying-Peng Zhang、Cheng-Zhong Zhang

  DOI：10.1021/np9904915

  日期：2000.5.1

  A novel bianthraquinone glycoside, 8-O-beta-D-glucopyranosyl-1,1', 8'-trihydroxy-3,3'-dimethyl-2,7'-bianthraquinone (1); two naphthalene derivatives, 2-acetyl-1-hydroxy-8-methoxy-3-methylnaphthalene (2) and 2-acetyl-1, 8-dimethoxy-3-methylnaphthalene (3); and a novel pre-anthraquinone, 1-oxo-4(S),9-dihydroxy-8-methoxy-6-hydroxymethyl-1,2,3, 4-tetrahydroanthracene (4), were isolated from Eremurus chinensis

  一种新型的蒽醌糖苷，8-O-β-D-吡喃葡萄糖基-1,1'，8'-三羟基-3,3'-二甲基-2,7'-蒽醌（1）; 两个萘衍生物：2-乙酰基-1-羟基-8-甲氧基-3-甲基萘（2）和2-乙酰基-1，8-二甲氧基-3-甲基萘（3）；并从中华绒螯蟹中分离出新型的前蒽醌1-氧代-4（S），9-二羟基-8-甲氧基-6-羟甲基-1,2,3,4-四氢蒽（4）。通过光谱和化学方法确定它们的结构。此外，还从中分离出了已知的化合物邻苯三酚，邻苯三酚8－甲醚，芦荟三酚8－甲基醚（5）和10-（邻苯三酚-7'-基）-10-羟基邻苯三酚-9-蒽酮。厂。
• Synthesis, biological evaluation, molecular docking and theoretical evaluation of ADMET properties of nepodin and chrysophanol derivatives as potential cyclooxygenase (COX-1, COX-2) inhibitors
  作者：Jagdeep Grover、Vivek Kumar、Vikram Singh、Khemraj Bairwa、M. Elizabeth Sobhia、Sanjay M. Jachak

  DOI：10.1016/j.ejmech.2014.04.033

  日期：2014.6

  Nepodin and chrysophanol, isolated from Rumex nepalensis roots, showed significant cyclooxygenase (COX) inhibitory activity. To further optimize these lead molecules and study structure activity relationship (SAR), eighteen derivatives of nepodin and nine derivatives of chrysophanol were synthesized and evaluated for COX-1 and COX-2 inhibitory potential. Among the synthesized compounds, four nepodin (1f, 1g, 1h and 1i) and three chrysophanol (2e, 2f and 2h) derivatives displayed more pronounced COX-2 inhibition than their respective lead molecule. Further, compounds 1f, 1g, 2e and 2h exhibited better anti-inflammatory activity than ibuprofen in carrageenan-induced rat paw edema assay. Taking into account the in vitro and in vivo results, molecular docking and in silico prediction of ADMET properties of compounds were carried out respectively.
• NISHIYAMA, TAKEO;KAMEOKA, HIROMU, NIPPON KAGAKU KAJSI,(1990) N, S. 699-701
  作者：NISHIYAMA, TAKEO、KAMEOKA, HIROMU

  DOI：——

  日期：——
• RIZZACASA, MARK A.;SARGENT, MELVYN V., AUSTRAL. J. CHEM., 41,(1988) N, C. 1087-1097
  作者：RIZZACASA, MARK A.、SARGENT, MELVYN V.

  DOI：——

  日期：——
• COMPOSITION COMPRISING AT LEAST ONE 1,8-DIHYDROXYNAPHTHALENE DERIVATIVE AND AT LEAST ONE BASIFYING AGENT DIFFERENT FROM AQUEOUS AMMONIA, PROCESS FOR DYEING KERATIN FIBRES USING THE COMPOSITION
  申请人：L'Oréal

  公开号：EP2488152B1

  公开（公告）日：2018-04-04

表征谱图