5-carbomethoxy-4-hydroxy-6-methyl-2H-pyran-2-one | 82697-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 5-carbomethoxy-4-hydroxy-6-methyl-2H-pyran-2-one
• 英文别名: 6-Methyl-5-carbomethoxy-4-hydroxy-2-pyrone；methyl 4-hydroxy-2-methyl-6-oxopyran-3-carboxylate
• CAS: 82697-66-3
• 化学式: C₈H₈O₅
• 分子量: 184.149
• InChiKey: GPZLWXXKOFEKOE-UHFFFAOYSA-N

物化性质

• 熔点：
  105-108 °C
• 沸点：
  268.9±40.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-carbomethoxy-4-hydroxy-6-methyl-2H-pyran-2-one 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 51.5h， 生成 4-Hydroxy-5-(2-methoxycarbonyl-ethyl)-2-methyl-6-oxo-6H-pyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Reduction of a-Pyrone Derivatives with Borane-Methyl Sulfide Complex

  摘要：

  Selective reduction of the 5-carbomethoxy- and the 5-carbethoxy-4-hydroxy-2H-pyran-2-one derivatives (5a approximately 11, 19) to yield the 5-hydroxymethyl derivatives (12 approximately 18) was accomplished using 1.1 mol equivalent of borane-methyl sulfide complex. Additionally, reduction of the 3-acetyl-4-hydroxy-2H-pyran-2-one derivatives (23, 26 and 29) with borane-methyl sulfide complex afforded the binary condensed pyrone derivatives (25, 28 and 3 1) in good yields.

  DOI：

  10.3987/com-93-6509
• 作为产物：
  描述：

  t-butyl-diphenylsilyl enol ether of methyl acetoacetate 、 丙二酰氯 在 硫酸 、 zinc dibromide 作用下， 生成 5-carbomethoxy-4-hydroxy-6-methyl-2H-pyran-2-one
  参考文献：
  名称：

  Reduction of a-Pyrone Derivatives with Borane-Methyl Sulfide Complex

  摘要：

  Selective reduction of the 5-carbomethoxy- and the 5-carbethoxy-4-hydroxy-2H-pyran-2-one derivatives (5a approximately 11, 19) to yield the 5-hydroxymethyl derivatives (12 approximately 18) was accomplished using 1.1 mol equivalent of borane-methyl sulfide complex. Additionally, reduction of the 3-acetyl-4-hydroxy-2H-pyran-2-one derivatives (23, 26 and 29) with borane-methyl sulfide complex afforded the binary condensed pyrone derivatives (25, 28 and 3 1) in good yields.

  DOI：

  10.3987/com-93-6509

文献信息

• Total Syntheses of Daldiniapyrone, Annularin B, and (±)-Annularin F
  作者：Richard Hsung、Aleksey Kurdyumov、R. Muñoz

  DOI：10.1055/s-2006-942355

  日期：2006.6

  The first concise total syntheses of daldiniapyrone, annularin B, and (±)-annularin F are described.

  本文首次对达迪尼亚酮、环烯醚萜醇 B 和环烯醚萜醇 F 进行了简要的全面综述。
• 1-aryl-1,4-dihydro-4-oxo-3,5-dicarboxypyridazine derivatives and their
  申请人：Rohm and Haas Company

  公开号：US04707181A1

  公开（公告）日：1987-11-17

  This invention relates to 1-aryl-1,4-dihydro-4-oxo-3,5-dicarboxypyridazine derivatives which are not only useful as plant growth regulators and hybridizing agents for cereal grain crops but possess the additional utility of having an improved margin of safety as concerns plant injury and seed quality.

  本发明涉及1-芳基-1,4-二氢-4-氧代-3,5-二羧基吡啶嗪衍生物，这些衍生物不仅可用作植物生长调节剂和杂交剂，还具有改进的安全边际，涉及植物损伤和种子质量。
• Substituted pyridazines, processes for making them, their use as plant growth regulators, and plant growth regulating compositions containing them
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0049971A1

  公开（公告）日：1982-04-21

  Novel substituted pyridazines are provided which exhibit plant growth regulating activity on gramineous plants such as cereals. The novel compounds are of Formula (I) wherein R' is (C1-C4) alkyl, phenyl or naphthyl each of the last two groups being optionally substituted with up to three of the same or different substituents selected from halogen, trihalomethyl, (C1-C4) alkoxy, (C1-C4) alkyl and cyano; R3 is hydrogen or a group as defined below for R5; R5 is a carboxy (-COOH) group or agronomically acceptable alkali metal salt thereof, an alkoxycarbonyl (-COOR) group or a substituted carbamoyl (-CONR'R") group, wherein R represents (C1-C4) alkyl, R' represents hydrogen or (C1-C4) alkyl and R" represents (C1-C4) alkyl; and R6 is a (C1-C4) alkyl group or an optionally substituted phenyl or naphthyl group as defined for R' above. Also provided are agronomically acceptable acid addition salts of compounds of Formula (I).

  本发明提供的新型取代哒嗪类化合物对禾本科植物（如谷物）具有植物生长调节活性。这些新型化合物如式 (I) 所示 其中，R'是(C1-C4)烷基、苯基或萘基，后两个基团中的每一个可任选被至多三个相同或不同的取代基取代，这些取代基可选自卤素、三卤甲基、(C1-C4)烷氧基、(C1-C4)烷基和氰基；R3 是氢或如下定义的 R5 基团；R5 是羧基 (-COOH) 或其农艺上可接受的碱金属盐、烷氧基羰基 (-COOR) 或取代的氨基甲酰基 (-CONR'R")，其中 R 代表 (C1-C4) 烷基，R'代表氢或 (C1-C4) 烷基，R "代表 (C1-C4) 烷基；以及 R6 是 (C1-C4) 烷基或任选取代的苯基或萘基，如上文对 R' 所定义。 还提供了农艺学上可接受的式 (I) 化合物的酸加成盐。
• Total Synthesis of Islandic Acid I Methyl Ester, Rosellisin and Rosellisin Aldehyde
  作者：Takeshi Shimizu、Sayoko Hiranuma、Tsumoru Watanabe、Masayuki Kirihara

  DOI：10.3987/com-93-6568

  日期：——

  Total synthesis of islandic acid I methyl ester (2), rosellisin (3) and rosellisin aldehyde (4) has been accomplished starting from 4-hydroxy-5-hydroxymethyl-6-methyl-2H-pyran-2-one (9a) via formylation of 9a with dichloromethyl methyl ether and titanium tetrachloride as a key step.
• PATTERSON, DENNIS R.
  作者：PATTERSON, DENNIS R.

  DOI：——

  日期：——