4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one | 20851-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one
• 英文别名: 4-hydroxy-6-(2-oxo-2-phenylethyl)pyran-2-one；4-hydroxy-6-(2-oxo-2-phenyl-ethyl)-pyran-2-one；4-Hydroxy-6-phenacyl-α-pyron；4-hydroxy-6-phenacylpyran-2-one
• CAS: 20851-38-1
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: AIMRGOBVEDTKLW-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C
• 沸点：
  425.4±45.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one 在 氢氧化钾 作用下， 生成 5-phenylresorcinol
  参考文献：
  名称：

  4-羟基-6-苯甲酰基-2-吡喃酮及相关化合物的芳构化反应

  摘要：

  用各种酸性和碱性试剂处理标题化合物导致内酯环裂解形成不稳定的中间体，该中间体以几种方式再循环。用强酸，该化合物被转化为γ-吡喃酮，亲核性碱被转化为间苯二酚，非亲核性碱转化为苯甲酰基间苯三酚。在前两个反应中，相应的3,5,7-三酮酸或酯是中间体。使用大量过量的螯合金属离子（Ca ++）导致可分离量的酯积累。提出了一种烯酮衍生物作为形成苯甲酰基间苯三酚的中间体。已经探索了标题吡喃酮的四种衍生物的反应。

  DOI：

  10.1016/s0040-4020(01)98735-6
• 作为产物：
  描述：

  4,6-dimethoxy-2-pyrone 在 碘代三甲硅烷 、 lithium diisopropyl amide 作用下， 以 氯仿 为溶剂， 反应 44.17h， 生成 4-hydroxy-6-(2-oxo-2-phenylethyl)-2H-pyran-2-one
  参考文献：
  名称：

  通过4,6-二甲氧基-2-吡喃酮与单和二酮阴离子的缩合反应制备3,5,7-三酮和3,5,7,9-四酮酸的烯醇内酯

  摘要：

  丙酮，苯乙酮，乙酰丙酮和苯甲酰丙酮的阴离子与4,6-二甲氧基-2-吡喃酮的缩合得到相应的6个取代的4-甲氧基-2-吡喃酮的良好收率，将其通过碘代三甲基硅烷脱甲基转化为4-羟基类似物。 。

  DOI：

  10.1016/s0040-4039(00)87236-6

文献信息

• Exploiting the Reaction Flexibility of a Type III Polyketide Synthase through in Vitro Pathway Manipulation
  作者：Jae-Cheol Jeong、Aravind Srinivasan、Sabine Grüschow、Horacio Bach、David H. Sherman、Jonathan S. Dordick

  DOI：10.1021/ja0441559

  日期：2005.1.1

  synthesis of the pentaketide flaviolin and its dimeric derivative, and a wide range of pyrones and their coupled derivatives with flaviolin, as well as their halogenated derivatives. The addition of acyl-CoA oxidase to the pathway prior to the polyketide synthase resulted in unsaturated pyrone side chains, further broadening the product spectrum that can be achieved. The approach developed in this work

  在体外构建了一个合成代谢途径，包括来自天蓝色链霉菌的 III 型聚酮化合物合酶和来自大豆和烟熏蓝藻（氯过氧化物酶）的过氧化物酶。这导致合成了五肽黄素及其二聚衍生物，以及广泛的吡喃酮及其与黄素的偶联衍生物，以及它们的卤化衍生物。在聚酮合酶之前将酰基辅酶A氧化酶添加到途径中导致不饱和的吡喃酮侧链，进一步拓宽了可以实现的产物谱。因此，这项工作中开发的方法为在复杂天然产物衍生物的合成中利用生物催化提供了一种新模型。
• In Vitro Precursor-Directed Synthesis of Polyketide Analogues with Coenzyme A Regeneration for the Development of Antiangiogenic Agents
  作者：Moon Il Kim、Seok Joon Kwon、Jonathan S. Dordick

  DOI：10.1021/ol901243e

  日期：2009.9.3

  Polyketide analogues are produced via in vitro reconstruction of a precursor-directed polyketide biosynthetic pathway. Malonyl-CoA synthetase (MCS) was used in conjunction with chalcone synthase (CHS), thereby allowing efficient use of synthetic starter molecules and malonate as extender. Coenzyme-A was recycled up to 50 times. The use of a simple immobilization procedure resulted in up to a 30-fold higher yield of pyrone CHS products than that obtained with the free enzyme solutions.
• Cloning and Structure-Function Analyses of Quinolone- and Acridone-producing Novel Type III Polyketide Synthases from Citrus microcarpa
  作者：Takahiro Mori、Yoshihiko Shimokawa、Takashi Matsui、Keishi Kinjo、Ryohei Kato、Hiroshi Noguchi、Shigetoshi Sugio、Hiroyuki Morita、Ikuro Abe

  DOI：10.1074/jbc.m113.493155

  日期：2013.10

  Two novel type III polyketide synthases, quinolone synthase (QNS) and acridone synthase (ACS), were cloned from Citrus microcarpa (Rutaceae). The deduced amino acid sequence of C. microcarpa QNS is unique, and it shared only 56-60% identities with C. microcarpa ACS, Medicago sativa chalcone synthase (CHS), and the previously reported Aegle marmelos QNS. In contrast to the quinolone- and acridone-producing A. marmelos QNS, C. microcarpa QNS produces 4-hydroxy-N-methylquinolone as the single product by the one-step condensation of N-methylanthraniloyl-CoA and malonyl-CoA. However, C. microcarpa ACS shows broad substrate specificities and produces not only acridone and quinolone but also chalcone, benzophenone, and phloroglucinol from 4-coumaroyl-CoA, benzoyl-CoA, and hexanoyl-CoA, respectively. Furthermore, the x-ray crystal structures of C. microcarpa QNS and ACS, solved at 2.47- and 2.35- resolutions, respectively, revealed wide active site entrances in both enzymes. The wide active site entrances thus provide sufficient space to facilitate the binding of the bulky N-methylanthraniloyl-CoA within the catalytic centers. However, the active site cavity volume of C. microcarpa ACS (760 (3)) is almost as large as that of M. sativa CHS (750 (3)), and ACS produces acridone by employing an active site cavity and catalytic machinery similar to those of CHS. In contrast, the cavity of C. microcarpa QNS (290 (3)) is significantly smaller, which makes this enzyme produce the diketide quinolone. These results as well as mutagenesis analyses provided the first structural bases for the anthranilate-derived production of the quinolone and acridone alkaloid by type III polyketide synthases.
• Enzymatic formation of unnatural novel polyketide scaffolds by plant-specific type III polyketide synthase
  作者：She-Po Shi、Hiroyuki Morita、Kiyofumi Wanibuchi、Hiroshi Noguchi、Ikuro Abe

  DOI：10.1016/j.tetlet.2009.02.170

  日期：2009.5

  The catalytic potential of octaketicle synthase (OKS), a plant-specific type III polyketide synthase (PKS) from Aloe arborescens, was investigated by phenylacetyl-CoA and benzoyl-CoA as starter substrates. As a result, a novel C-16 pentaketide coumarin was produced from phenylacetyl-CoA, whereas benzoyl-CoA was not a good substrate of OKS. Remarkably, a structure-guided OKS N222G mutant dramatically extended the product chain length to yield four novel polyketides including C-22 aromatic octaketides from the C-6-C-2 phenylacetyl starter, as well as a novel C-19 heptaketide benzophenone from the C-6-C-1 benzoyl starter. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.