4-hydroxy-6-styryl-2H-pyran-2-one | 2082-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hydroxy-6-styryl-2H-pyran-2-one
• 英文别名: 4-Hydroxy-6-styryl-2-pyrone；4-hydroxy-6-(2-phenylethenyl)pyran-2-one
• CAS: 2082-94-2
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: LGSQMZHPXAWUAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-styryl-2H-pyran-2-one 、 S-苯基硫代苯基砜 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 48.0h， 以68%的产率得到4-hydroxy-6-(2-phenylethenyl)-3-(phenylsulfanyl)-2H-pyran-2-one
  参考文献：
  名称：

  Easy and green synthesis of 6-(arylvinyl)-4-hydroxy-3-(phenylsulfanyl)-2H-pyran-2-ones in aqueous potassium hydroxide

  摘要：

  DOI：

  10.1134/s1070363216120550
• 作为产物：
  描述：

  去氢乙酸 在 硫酸 、 sodium hydride 、 potassium carbonate 、 乙硫醇 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 、 mineral oil 为溶剂， 反应 23.65h， 生成 4-hydroxy-6-styryl-2H-pyran-2-one
  参考文献：
  名称：

  Easy and green synthesis of 6-(arylvinyl)-4-hydroxy-3-(phenylsulfanyl)-2H-pyran-2-ones in aqueous potassium hydroxide

  摘要：

  DOI：

  10.1134/s1070363216120550

文献信息

• Bioinspired total synthesis of katsumadain A by organocatalytic enantioselective 1,4-conjugate addition
  作者：Yongguang Wang、Ruiyang Bao、Shengdian Huang、Yefeng Tang

  DOI：10.3762/bjoc.9.182

  日期：——

  Katsumadain A, a naturally occurring in fl uenza virus neuraminidase (NA) inhibitor, was synthesized by using a bioinspired, organocatalytic enantioselective 1,4-conjugate addition of styryl-2-pyranone with cinnamaldehyde, followed by a tandem Horner-Wadsworth-Emmons/oxa Michael addition.

  Katsumadain A 是一种天然存在于流感病毒神经氨酸酶 (NA) 的抑制剂，通过使用生物启发的有机催化对映选择性 1,4-共轭加成与肉桂醛苯乙烯基-2-吡喃酮，然后是串联的 Horner-Wadsworth-Emmons/奥沙迈克尔加法。
• Enzymatic synthesis of kavalactones and flavokavains
  申请人：Whitehead Institute for Biomedical Research

  公开号：US10941429B2

  公开（公告）日：2021-03-09

  Disclosed are methods, compositions, proteins, nucleic acids, cells, vectors, compounds, reagents, and systems for the preparation of kavalactones, flavokavains, and kavalactone and flavokavain biosynthetic intermediates using enzymes expressed in heterologous host cells, such as microorganisms or plants, or using in vitro enzymatic reactions. This invention also provides for the expression of the enzymes by recombinant cell lines and vectors. Furthermore, the enzymes can be components of constructs such as fusion proteins. The kavalactones produced can be utilized to treat anxiety disorder, insomnia, and other psychological and neurological disorders. The flavokavains produced can be utilized to treat various cancers including colon, bladder, and breast cancers.

  本发明公开了利用在异源宿主细胞（如微生物或植物）中表达的酶或利用体外酶促反应制备卡瓦内酯、黄酮素以及卡瓦内酯和黄酮素生物合成中间体的方法、组合物、蛋白质、核酸、细胞、载体、化合物、试剂和系统。本发明还提供了通过重组细胞系和载体表达酶的方法。此外，酶还可以是融合蛋白等构建体的组成部分。生产的卡瓦内酯可用于治疗焦虑症、失眠症以及其他心理和神经疾病。生产的黄酮类化合物可用于治疗各种癌症，包括结肠癌、膀胱癌和乳腺癌。
• Synthesis of γ-Thiapyrones by Diels–Alder/Retro-Diels–Alder Reaction of α-Pyrones with 5-H-1,2,3-Thiadiazoles
  作者：Mengxia Feng、Bin Huang、Huanfeng Jiang、Liangbin Huang

  DOI：10.1021/acs.joc.3c02889

  日期：2024.4.19

  The efficient synthesis of γ-thiapyrones by a base-mediated Diels–Alder/retro-Diels–Alder reaction of α-pyrones with 5-H-1,2,3-thiadiazoles is reported herein. Thioketenes in situ generated from thiadiazoles as electron-poor dienophile and electron-rich 4-hydroxy-2-pyrones as dienes are conjunctively transformed into a series of γ-thiapyrones with broad functional group compatibility in good to excellent

  本文报道了通过 α-吡喃酮与 5- H -1,2,3-噻二唑的碱介导的 Diels-Alder/retro-Diels-Alder 反应有效合成 γ-噻喃酮。由作为缺电子亲二烯体的噻二唑和作为二烯的富电子 4-羟基-2-吡喃酮原位生成的硫烯酮被联合转化为一系列具有广泛官能团相容性的 γ-噻喃酮，产率良好到优异（35 个例子，67%）平均产量）。
• 一种γ‐噻喃酮衍生物的高效合成方法
  申请人：华南理工大学

  公开号：CN117126131A

  公开（公告）日：2023-11-28

  本发明属于有机发光的技术领域，公开了一种γ‑噻喃酮衍生物的高效合成方法。方法：以极性有机溶剂为反应介质，将噻二唑类化合物和4‑羟基吡喃酮类化合物在碱性化合物的作用下反应，获得γ‑噻喃酮衍生物。所述γ‑噻喃酮衍生物的结构为式III。本发明的方法反应条件温和、无需过渡金属催化剂，能耗低有利于环境保护且有利于工业化规模生产；且本发明的方法具有高度化学选择性，产物收率高，反应底物范围广，官能团兼容性强。本发明的γ‑噻喃酮衍生物制备的荧光有机化合物作为荧光探针具有较宽吸收范围、斯托克斯位移大、发射波长较长等特点。#imgabs0#
• 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.