2-乙烯基-2,3-二氢吡喃-4-酮 | 82093-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2-乙烯基-2,3-二氢吡喃-4-酮
• 英文名称: 2-vinyl-2H-pyran-4(3H)-one
• 英文别名: 2-ethenyl-2,3-dihydropyran-4-one
• CAS: 82093-20-7
• 化学式: C₇H₈O₂
• 分子量: 124.139
• InChiKey: UJIIBZRKGQNPSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙烯基-2,3-二氢吡喃-4-酮 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 copper(l) iodide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (E)-2-(4-methoxystyryl)-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells

  摘要：

  The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the gamma-pyrones and the azagoniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin ( 1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.059
• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 丙烯醛 在 三氟化硼乙醚 、 水 、 碳酸氢钠 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.67h， 以70%的产率得到2-乙烯基-2,3-二氢吡喃-4-酮
  参考文献：
  名称：

  Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells

  摘要：

  The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the gamma-pyrones and the azagoniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin ( 1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.059

文献信息

• On the Lewis acid catalyzed cyclocondensation of silyloxydienes with .alpha.,.beta.-unsaturated aldehydes
  作者：Samuel Danishefsky、James F. Kerwin

  DOI：10.1021/jo00137a035

  日期：1982.7
• A Simple, One-Pot Synthesis of 2,3-Dihydro-4<i>H</i>-pyran-4-ones via the Acid-Catalysed [4 + 2]-Cycloaddition of 1-Alkoxy-3-trimethylsilyloxy-1,3-butadienes with Aldehydes
  作者：René W. Aben、Hans W. Scheeren

  DOI：10.1055/s-1982-29943

  日期：——
• DANISHEFSKY S.;KERWIN J. F., J. ORG. CHEM., 1982, 47, NO 16, 3183-3184
  作者：DANISHEFSKY S.、KERWIN J. F.

  DOI：——

  日期：——
• Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells
  作者：Rosimeire Coura Barcelos、Julio Cezar Pastre、Vanessa Caixeta、Débora Barbosa Vendramini-Costa、João Ernesto de Carvalho、Ronaldo Aloise Pilli

  DOI：10.1016/j.bmc.2012.03.059

  日期：2012.6

  The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the gamma-pyrones and the azagoniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin ( 1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds. (C) 2012 Elsevier Ltd. All rights reserved.