6-(2,4-二羟基-6-甲基苯基)-4-甲氧基吡喃-2-酮 | 59163-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 6-(2,4-二羟基-6-甲基苯基)-4-甲氧基吡喃-2-酮
• 英文名称: 4-methoxy-6-(2',4'-dihydroxy-6'-methylphenyl)-pyran-2-one
• 英文别名: 4-methoxy-6-(2',4'-dihydroxy-6'-methylphenyl)pyran-2-one；6-(2',4'-dihydroxy-6'-methylphenyl)-4-methoxy-2-pyrone；aloenin aglycone；Aloenin-Aglycon；6-(2,4-dihydroxy-6-methyl-phenyl)-4-methoxy-pyran-2-one；2H-Pyran-2-one, 6-(2,4-dihydroxy-6-methylphenyl)-4-methoxy-；6-(2,4-dihydroxy-6-methylphenyl)-4-methoxypyran-2-one
• CAS: 59163-53-0
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: GJWNAMOGOKAELX-UHFFFAOYSA-N

物化性质

• 熔点：
  212-213 °C
• 沸点：
  539.0±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  芦荟宁	6-(2'-O-β-D-glucopyranosyl-4'-hydroxy-6'-methylphenyl)-4-methoxy-2-pyrone	38412-46-3	C19H22O10	410.378

反应信息

• 作为反应物：
  描述：

  6-(2,4-二羟基-6-甲基苯基)-4-甲氧基吡喃-2-酮 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 生成 6-(2,4-diacetoxy-6-methyl-phenyl)-4-methoxy-pyran-2-one
  参考文献：
  名称：

  Anthraquinone, anthrone and phenylpyrone components of Aloe nyeriensis var. kedongensis leaf exudate

  摘要：

  The leaf exudate of Aloe nyeriensis var. kedongensis yielded six compounds which were identified on the basis of spectral data and inter-conversions as two groups of three allied compounds. These were (a) 4-methoxy-6-(2'',4''-dihydroxy-6''-methylphenyl)-pyran-2-one, its 2''-O-.beta.-D-glucopyranoside (aloenin) and the 2"-O-p-coumaroyl ester of aloenin, (b) the anthracene derivatives 1,2,8-trihydroxy-6-methylanthraquinone (nataloe-emodin), its 2-O-.beta.-D-glucopyranosyl ester and the corresponding 10-C-.beta.-D-glucopyranoside nataloin.

  DOI：

  10.1016/s0031-9422(00)84578-1
• 作为产物：
  描述：

  1-(2,4-Dihydroxy-6-methylphenyl)-2-(2-methyl-1,3-dioxolan-2-yl)ethanon 在 10% palladium on active carbon 盐酸 、 1,2-二溴四氯乙烷 、 氢气 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 2.33h， 生成 6-(2,4-二羟基-6-甲基苯基)-4-甲氧基吡喃-2-酮
  参考文献：
  名称：

  乙酰乙酸异辛啉-碱，5. Aufbau和Cyclisierung末端geschützterβ-戊酮：Erste Synthese des Aloenin-Aglycons

  摘要：

  单缩醛6b和双缩醛6c，β-五角大楼衍生衍生物6a，深层酯交换反应。Die spezifische Cyclisierung von 6b zu dem Resorcin-Derivat 15a wird zu einem ersten Syntheseweg zum Aglycon 2b des biologisch aktiven Bitterglucosids Aloenin（2a）ausgebaut。NOCH恩格河畔Biosynthese orientiert IST DER dadurch besonders stufenarme zweite Zugangつ2B黚死诺尔最小geschützteβ-Polycarbonylsäure 20。

  DOI：

  10.1002/jlac.198519850412

文献信息

• Natural and Synthetic 6-Aryl Pyrones. An Unexpected Reaction of Dihydropyrones with NBS Leads to the First Synthesis of Allantopyrone C
  作者：George A. Kraus、Kyle Podolak

  DOI：10.1055/a-1924-1324

  日期：2023.1

  Nigerapyrone A, aloenin aglycone, 4′-methyl klavuzon, and allantopyrone C were synthesized from commercially available aldehydes.

  Nigerapyrone A、芦荟苷苷元、4'-甲基克拉夫宗和尿囊素 C 由市售的醛合成。
• Pyrone polyketides synthesized by a type III polyketide synthase from Drosophyllum lusitanicum
  作者：Aphacha Jindaprasert、Karin Springob、Jürgen Schmidt、Wanchai De-Eknamkul、Toni M. Kutchan

  DOI：10.1016/j.phytochem.2008.03.013

  日期：2008.12

  To isolate cDNAs involved in the biosynthesis of acetate-derived naphthoquinones in Drosophyllum lusitanicum, an expressed sequence tag analysis was performed. RNA from callus cultures was used to create a cDNA library from which 2004 expressed sequence tags were generated. One cDNA with similarity to known type III polyketicle synthases was isolated as full-length sequence and termed DluHKS. The translated polypepticle sequence of DIuHKS showed 51-67% identity with other plant type III PKSs. Recombinant DIuHKS expressed in Escherichia coli accepted acetyl-coenzyme A (CoA) as starter and carried out sequential decarboxylative condensations with malonyl-CoA yielding ot-pyrones from three to six acetate units. However, naphthalenes, the expected products, were not isolated. Since the main compound produced by DIuHKS is a hexaketicle ot-pyrone, and the naphthoquinones in D. lusitanicum are composed of six acetate units, we propose that the enzyme provides the backbone of these secondary metabolites. An involvement of accessory proteins in this biosynthetic pathway is discussed. (c) 2008 Elsevier Ltd. All rights reserved.
• BRINGMANN, G.;SCHNEIDER, S., SYNTHESIS, BRD, 1983, N 2, 139-141
  作者：BRINGMANN, G.、SCHNEIDER, S.

  DOI：——

  日期：——
• Acetogenine Isochinolin-Alkaloide, 5. Aufbau und Cyclisierung terminal geschützter β-Pentaketone: Erste Synthese des Aloenin-Aglycons
  作者：Gerhard Bringmann、Stephan Schneider

  DOI：10.1002/jlac.198519850412

  日期：1985.4.15

  Das Monoacetal 6b und das Diacetal 6c, Derivate des freien β-Pentaketons 6a, werden aus einfachen Vorstufen durch Esterkondensation dargestellt. Die spezifische Cyclisierung von 6b zu dem Resorcin-Derivat 15a wird zu einem ersten Syntheseweg zum Aglycon 2b des biologisch aktiven Bitterglucosids Aloenin (2a) ausgebaut. Noch enger an der Biosynthese orientiert ist der dadurch besonders stufenarme zweite

  单缩醛6b和双缩醛6c，β-五角大楼衍生衍生物6a，深层酯交换反应。Die spezifische Cyclisierung von 6b zu dem Resorcin-Derivat 15a wird zu einem ersten Syntheseweg zum Aglycon 2b des biologisch aktiven Bitterglucosids Aloenin（2a）ausgebaut。NOCH恩格河畔Biosynthese orientiert IST DER dadurch besonders stufenarme zweite Zugangつ2B黚死诺尔最小geschützteβ-Polycarbonylsäure 20。
• Anthraquinone, anthrone and phenylpyrone components of Aloe nyeriensis var. kedongensis leaf exudate
  作者：John M. Conner、Alexander I. Gray、Tom Reynolds、Peter G. Waterman

  DOI：10.1016/s0031-9422(00)84578-1

  日期：——

  The leaf exudate of Aloe nyeriensis var. kedongensis yielded six compounds which were identified on the basis of spectral data and inter-conversions as two groups of three allied compounds. These were (a) 4-methoxy-6-(2'',4''-dihydroxy-6''-methylphenyl)-pyran-2-one, its 2''-O-.beta.-D-glucopyranoside (aloenin) and the 2"-O-p-coumaroyl ester of aloenin, (b) the anthracene derivatives 1,2,8-trihydroxy-6-methylanthraquinone (nataloe-emodin), its 2-O-.beta.-D-glucopyranosyl ester and the corresponding 10-C-.beta.-D-glucopyranoside nataloin.