3-formyl-1-methoxy-6-oxocyclohexa-2,4-dienyl acetate | 6520-85-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-formyl-1-methoxy-6-oxocyclohexa-2,4-dienyl acetate
• 英文别名: 2-acetoxy-4-formyl-2-methoxy-3,5-cyclohexadienone；3-acetoxy-3-methoxy-4-oxo-cyclohexa-1,5-dienecarbaldehyde；3-Acetoxy-3-methoxy-4-oxo-cyclohexa-1,5-diencarbaldehyd；3-Methoxy-3-acetoxy-4-oxo-3,4-dihydro-benzaldehyd；Vanillin-o-chinolacetat；(3-Formyl-1-methoxy-6-oxocyclohexa-2,4-dien-1-yl) acetate
• CAS: 6520-85-0
• 化学式: C₁₀H₁₀O₅
• 分子量: 210.186
• InChiKey: VOQPPYSAZNZLMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-formyl-1-methoxy-6-oxocyclohexa-2,4-dienyl acetate 生成 2-azido-4-hydroxy-3-methoxy-benzaldehyde
  参考文献：
  名称：

  �ber die Darstellung von Azidophenolen

  摘要：

  DOI：

  10.1007/bf00902587
• 作为产物：
  描述：

  乙酸酐 、 香草醛 在 sodium periodate 作用下， 以59%的产率得到3-formyl-1-methoxy-6-oxocyclohexa-2,4-dienyl acetate
  参考文献：
  名称：

  Novel One‐Pot Synthesis of Acetoxy‐2,4‐Cyclohexadienones

  摘要：

  A new, simple, one-pot method for the oxidative acetylation of some substituted phenols leading to acetoxycyclohexa-2,4-dienones is described. A novel diacetoxycyclohexadienone 12 has also been prepared using the present method from 2-hydroxymethyl phenol (salicyl alcohol).

  DOI：

  10.1081/scc-200061717

文献信息

• Structural Studies on Bioactive Compounds. 32. Oxidation of Tyrphostin Protein Tyrosine Kinase Inhibitors with Hypervalent Iodine Reagents
  作者：Geoffrey Wells、Angela Seaton、Malcolm F. G. Stevens

  DOI：10.1021/jm990947f

  日期：2000.4.1

  Hydroxylated styrenes (tyrphostins) undergo oxidation by hypervalent iodine oxidants such as [(diacetoxy)iodo]benzene (DAIB) to give a range of products depending on the structure of the phenolic substrate, the solvent, the oxidant stoichiometry, and the purification strategy. Conditions have been developed to modify the phenolic component of the tyrphostin without affecting the appended substituted-vinyl moiety. Novel products include: unstable 2-acyloxy-2-methoxy-4-(substituted-vinyl)cyclohexadienones and their rearrangement products 2-acyloxy-4-hydroxy-3 -methoxy-1-(substituted-vinyl)benzenes; phenyliodoniophenolates and their rearrangement products iodophenoxytyrphostins; and 3,3'-dialkoxy-2,2'-dihydroxy-5,5'-di(substituted-vinyl)biphenyls. None of these oxidation products displayed enhanced activity in vitro in the NCI 60-cell line panel or in a panel of human breast cancer cell lines, compared to their tyrphostin precursors. The inhibitory activity of three representative tyrphostins (3e,n, 28) was not modulated by aerobic/anaerobic conditions in MCF-7 and MDA 468 cells and was independent of EGFR status in clones of ZR75B cells transfected with this receptor. Basal growth of MCF-7 cells was unaffected by co-administration of the growth factors EGF, TGF-alpha, IGF-I, and IGF-II, and the new agents did not inhibit EGFR and c-erbB2 autaphosphorylation in cell lysates from MDA 468 or SkBr3 cells, respectively, suggesting that receptor tyrosine kinases are not targets for these compounds. Growth stimulation by the tyrphostin 3n in the ER+ breast cell lines MCF-7, T47D, and ZR75-1 was abolished by 1 mu M tamoxifen, suggesting that this compound has estrogen agonist activity.
• �ber die Einwirkung von Bleitetraacetat auf Phenole IV
  作者：F. Wessely、J. Kotlan

  DOI：10.1007/bf00899193

  日期：——
• �ber Reaktionen der o-Chinolacetate des Vanillins und Isovanillins, 1. Mitt.
  作者：F. Wessely、M. Grossa

  DOI：10.1007/bf00905275

  日期：——
• Untersuchungen �ber Chinole. IV
  作者：F. Wessely、W. Metlesics

  DOI：10.1007/bf00902314

  日期：——
• �ber die Darstellung von Azidophenolen
  作者：M. Grossa、F. Wessely

  DOI：10.1007/bf00902587

  日期：——