5-甲氧基-4H-吡喃-4-酮-2-甲醛 | 35438-43-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 5-甲氧基-4H-吡喃-4-酮-2-甲醛
• 英文名称: 5-methoxy-4-oxo-4H-pyran-2-carbaldehyde
• 英文别名: Comenaldehyd-methylaether；5-methoxy-4-oxopyran-2-carbaldehyde
• CAS: 35438-43-8
• 化学式: C₇H₆O₄
• mdl: MFCD16653147
• 分子量: 154.122
• InChiKey: MUGFZMFHXQIFFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  206 °C
• 沸点：
  359.7±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  5-甲氧基-4H-吡喃-4-酮-2-甲醛 在 aluminum (III) chloride 作用下， 反应 3.0h， 以56%的产率得到comenaldehyde
  参考文献：
  名称：

  Refinement of arylthiosemicarbazone pharmacophore in inhibition of mushroom tyrosinase

  摘要：

  Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin biosynthesis, it catalyzes the transformation of tyrosine into L-dopaquinone. The aim of the present study was to study molecules able to inhibit tyrosinase to be used in treating depigmentation-related disorders. In this study, we targeted arylthiosemicarbazone analogs with the aim to contribute to the identification of the optimal aryl ring to be linked to the thiosemicarbazone moiety. The biological activity was evaluated on commercial mushroom tyrosinase which was purified prior use. The results demonstrated that several of our compounds (1a-h, 1j, 1r and 5) had more potent inhibitory activities than kojic acid which was used as the reference inhibitor. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.003
• 作为产物：
  描述：

  2-(羟基甲基)-5-甲氧基-4H-吡喃-4-酮 在 manganese(IV) oxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 5-甲氧基-4H-吡喃-4-酮-2-甲醛
  参考文献：
  名称：

  NITROGEN-CONTAINING HETEROCYCLIC COMPOUND

  摘要：

  公开号：

  EP3156397B1

文献信息

• Synthesis of Novel Pyrone, Chromone and Coumarin Derivatives of Aminomethanephosphonic Acid
  作者：Bogdan Boduszek、Michal Uher

  DOI：10.1080/00397910008087219

  日期：2000.4

  Abstract Novel pyrone, chromone and coumarin derivatives of aminomethanephosphonic acid were obtained in a one-step process, by treatment of a mixture of heterocyclic aldehyde and amine with tris(trimethylsilyl)phosphite, and a subsequent solvolysis of the formed silylated product with methanol.

  摘要 通过用亚磷酸三(三甲基甲硅烷基)酯处理杂环醛和胺的混合物，随后用甲醇对形成的甲硅烷基化产物进行溶剂分解，一步法制备了氨基甲膦酸的新型吡喃酮、色酮和香豆素衍生物。
• Conversion of Formyl into Cyano groups in kojic acid derivatives and analogues
  作者：Jacek M?ochowski、Miroslaw Giurg、Michal Uher、Anna Korenova、Daniel Vegh

  DOI：10.1002/prac.19963380111

  日期：——

  It has been revealed that N,N-dimethylhydrazones (1a-c, 3a,b) derived from kojic acid analogs, such as substituted furans (3a,b), 4-pyrones (1a,b) and 4-pyridine (1c), on oxididation with 3-chloroperoxybenzoic acid afford the corresponding nitriles (2a-c, 4a,b). The method has preparative value. The mechanism of the reaction is presented.
• Arnarp, Jan; Bielawski, Jacek; Dahlin, Britt-Marie, Acta Chemica Scandinavica, 1990, vol. 44, # 7, p. 916 - 926
  作者：Arnarp, Jan、Bielawski, Jacek、Dahlin, Britt-Marie、Dahlman, Olof、Enzell, Curt R.、Pettersson, Tore

  DOI：——

  日期：——
• Pyrones: V—The mass spectra and fragmentation mechanisms of some 3(5)-methoxy-4-pyrones
  作者：David L. McGillivray、Gerald A. Poulton

  DOI：10.1002/oms.1210150110

  日期：1980.1

  AbstractThe mass spectra of methyl kojate (2‐hydroxymethyl‐5‐methoxy‐4H‐pyran‐4‐one), two deuterated analogues and 14 related 3(5)‐methoxy‐4‐pyrones have been studied. These compounds fragment according to a common mechanism, initiated by primary rearrangement of the molecular ion(s). Guidelines which indicate the presence of 3(5)‐methoxy‐4‐pyrones and allow structural determinations to be made from their mass spectra are presented. For the majority of substituents studied, the nature of the substituent has no major effect upon the fragmentation pattern; the cyano group does. The hydroxy counterparts of the above compounds are readily converted for analysis by simple methylation.
• Re-examination of Nucleophilic Substitutionin Chlorokojic Acid
  作者：Michal Uher、Joanna Szymońska、Anna Korenova、Piotr Tomasik

  DOI：10.1007/s007060070106

  日期：2000.3.16

  Chlorokojic acid was reacted with S2O32-, NO3-, N-3(-), I-, and SCN-. Only the three latter nucleophiles substituted the chlorine atom in the 2-CH2Cl group of kojic acid. In none of the products nucleophilic substitution at position 6 of the 4-pyrone could be found. Regular substituion of chlorokojic acid with I- (iodokojic acid), N-3(-) (azidokojic acid), and SCN- (thiocyanato and isothiocyanato kojic acids) was accompanied by formation of allomaltol. Reaction pathways for the formation of allomaltol and 6-substituted allomaltol derivatives are proposed. The latter has been formerly discovered in the reaction of chlorokojic acid with secondary amines.