3-[(2E)-3-(4-bromophenyl)prop-2-enoyl]-4-hydroxy-6-methyl-2H-pyran-2-one | 1006372-28-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-[(2E)-3-(4-bromophenyl)prop-2-enoyl]-4-hydroxy-6-methyl-2H-pyran-2-one
• 英文别名: 3-[(E)-3-(4-bromophenyl)prop-2-enoyl]-4-hydroxy-6-methyl-pyran-2-one；3-[(E)-3-(4-bromophenyl)prop-2-enoyl]-4-hydroxy-6-methylpyran-2-one
• CAS: 1006372-28-6
• 化学式: C₁₅H₁₁BrO₄
• 分子量: 335.154
• InChiKey: HEVVWTXGHMEBER-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  3-[(2E)-3-(4-bromophenyl)prop-2-enoyl]-4-hydroxy-6-methyl-2H-pyran-2-one 、 溶剂黄146 在 一水合肼 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以83%的产率得到3-[1-acetyl-5-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-3-yl]-4-hydroxy-6-methyl-2H-pyran-2-one
  参考文献：
  名称：

  1,5-二取代的3-（4-羟基-6-甲基-2-氧代-2 H- 吡喃-3-基）-2-吡唑啉的合成

  摘要：

  通过衍生自α，β-不饱和酮的反应，合成了一系列的1,5-二取代的3-（4-羟基-6-甲基-2-氧代 -2- H- 吡喃-3-基）-2-吡唑啉脱氢乙酸和肼在热乙酸或丙酸中。通过显微分析，1 H和13 C NMR，IR和质谱测量，阐明了所有新化合物的结构。

  DOI：

  10.1007/s00706-006-0437-9
• 作为产物：
  描述：

  3-[(2E)-3-(4-bromophenyl)prop-2-enoyl]-6-methyl-2-oxo-2H-pyran-4-yl difluoridoborate 在 水 、 sodium carbonate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以63%的产率得到3-[(2E)-3-(4-bromophenyl)prop-2-enoyl]-4-hydroxy-6-methyl-2H-pyran-2-one
  参考文献：
  名称：

  Discovery of 3-acetyl-4-hydroxy-2-pyranone derivatives and their difluoridoborate complexes as a novel class of HIV-1 integrase Inhibitors

  摘要：

  HIV-1 integrase (IN) has emerged as an important therapeutic target for anti-HIV drug development. Its uniqueness to the virus and its critical role in the viral life cycle makes IN suitable for selective inhibition. The recent approval of Raltegravir (MK-0518) has created a surge in interest and great optimism in the field. In our ongoing IN drug design research, we herein report the discovery of substituted analogs of 3-acetyl-4-hydroxy-2-pyranones and their difluoridoborate complexes as novel IN inhibitors. In many of these compounds, complexation with boron difluoride increased the potency and selectivity of IN inhibition. Compound 9 was most active with an IC50 value of 9 mu M and 3 mu M for 3'-processing and strand transfer inhibition, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.067

文献信息

• Regioselective Synthesis of Novel Spiropyrrolidines and Spirothiapyrrolizidines Through Multicomponent 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylides
  作者：Hai Liu、Guolan Dou、Daqing Shi

  DOI：10.1021/cc100035q

  日期：2010.9.13

  A series of novel spiropyrrolidines and spirothiapyrrolizidines were synthesized via a three-component 1,3-dipolar cycloaddition reaction of isatin or acenaphthenequinone, sarcosine or thiaproline and 4-hydroxy-6-methyl-3-((E)-3-phenylacryloyl)-2H-pyran-2-ones in refluxing ethanol. Advantages of this method include the availability of starting materials, mild reaction conditions, high yields, and the

  一系列新的螺吡咯烷和螺吡咯并吡咯烷是通过靛红或atin啶醌，肌氨酸或硫代脯氨酸与4-羟基-6-甲基-3-（（E）-3-苯基丙烯酰基）-的三组分1,3-偶极环加成反应合成的在回流的乙醇中的2 H-吡喃-2-酮。该方法的优点包括可获得原料，温和的反应条件，高收率和观察到的完全区域选择性。
• Discovery of 3-acetyl-4-hydroxy-2-pyranone derivatives and their difluoridoborate complexes as a novel class of HIV-1 integrase Inhibitors
  作者：Kavya Ramkumar、Konstantin V. Tambov、Rambabu Gundla、Alexandr V. Manaev、Vladimir Yarovenko、Valery F. Traven、Nouri Neamati

  DOI：10.1016/j.bmc.2008.08.067

  日期：2008.10

  HIV-1 integrase (IN) has emerged as an important therapeutic target for anti-HIV drug development. Its uniqueness to the virus and its critical role in the viral life cycle makes IN suitable for selective inhibition. The recent approval of Raltegravir (MK-0518) has created a surge in interest and great optimism in the field. In our ongoing IN drug design research, we herein report the discovery of substituted analogs of 3-acetyl-4-hydroxy-2-pyranones and their difluoridoborate complexes as novel IN inhibitors. In many of these compounds, complexation with boron difluoride increased the potency and selectivity of IN inhibition. Compound 9 was most active with an IC50 value of 9 mu M and 3 mu M for 3'-processing and strand transfer inhibition, respectively. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of 1,5-Disubstituted 3-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-pyrazolines
  作者：Albert Lévai、József Jekő

  DOI：10.1007/s00706-006-0437-9

  日期：2006.3

  A series of 1,5-disubstituted 3-(4-hydroxy-6-methyl-2-oxo-2 H -pyran-3-yl)-2-pyrazolines were synthesized by the reaction of α,β-unsaturated ketones derived from dehydroacetic acid and hydrazine in hot acetic acid or propionic acid. The structures of all new compounds were elucidated by microanalyses, 1H and 13C NMR, IR, and mass spectroscopic measurements.

  通过衍生自α，β-不饱和酮的反应，合成了一系列的1,5-二取代的3-（4-羟基-6-甲基-2-氧代 -2- H- 吡喃-3-基）-2-吡唑啉脱氢乙酸和肼在热乙酸或丙酸中。通过显微分析，1 H和13 C NMR，IR和质谱测量，阐明了所有新化合物的结构。