3-(4-methoxyphenyl)-4,6-diphenyl-2H-pyran-2-one | 1172584-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxyphenyl)-4,6-diphenyl-2H-pyran-2-one
• 英文别名: 3-(4-Methoxyphenyl)-4,6-diphenylpyran-2-one
• CAS: 1172584-19-8
• 化学式: C₂₄H₁₈O₃
• 分子量: 354.405
• InChiKey: SXSXRLFBMIUHNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-4,6-diphenyl-2H-pyran-2-one 在 吡啶盐酸盐 作用下， 反应 2.0h， 以72%的产率得到3-(4-hydroxyphenyl)-4,6-diphenyl-pyran-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 3,4,6-triaryl-2-pyranones as a potential new class of anti-breast cancer agents

  摘要：

  A series of 3,4,6-triaryl-2-pyranones, new class of anti-breast cancer agents, have been synthesized as a structural variants of cyclic triphenylethylenes by replacing the fused benzene ring with pendant phenyl ring to mimic the phenolic A ring of estradiol. Nine of these newly synthesized pyranones exhibited significant anti-proliferative activity in both ER+ve and ER-ve breast cancer cell lines. Four active non-cytotoxic compounds 5c, 5d, 5g and 5h showed specific and selective cytotoxicity and two compounds 5d and 5h induced significant DNA fragmentation in both MCF-7 and MDA-MB-231 cell lines. Based on RBA studies, the molecules probably act in an ER-independent mechanism. The involved pathway was observed as caspase-dependant apoptosis in MCF-7 cells. However, the particular caspases involved and the possible cellular target through which this series of compounds mediate cell death are not known. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.032
• 作为产物：
  描述：

  methyl 2-benzoyl-1-(4-methoxyphenyl)-3-phenylcyclopropane-1-carboxylate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到3-(4-methoxyphenyl)-4,6-diphenyl-2H-pyran-2-one
  参考文献：
  名称：

  通过 TfOH 介导的 2-酰基环丙烷-1-羧酸酯的扩环轻松合成多取代的 2-吡喃酮

  摘要：

  报道了一种从容易获得的 2-酰基环丙烷-1-芳基-1-羧酸酯通过 TfOH 介导多取代 2-吡喃酮的简便途径。强供体 1-芳基对于指导供体-受体环丙烷环的 C-C 键断裂很重要，然后通过内酯化形成 2-吡喃酮环。

  DOI：

  10.1055/a-1526-7839

文献信息

• Base- and sulfur-promoted oxidative lactonization of chalcone-acetate Michael adducts: access to pyran-2-ones
  作者：Cao Nguyen Nguyen、Duc Toan Nguyen、Ha An Tran、Dinh Hung Mac、Thi Thu Tram Nguyen、Pascal Retailleau、Thanh Binh Nguyen

  DOI：10.1039/d4ob00479e

  日期：——

  A cost-effective, practical, straightforward and scalable synthesis of α-pyrones via base- and sulfur-promoted annulation of phenylacetates and chalcones is reported. Generated in situ from the starting components by using dbu as a base catalyst, the Michael adducts underwent a smooth oxidative cyclization into 3,4,6-triaryl-2-pyranones upon heating with DABCO and sulfur in DMSO. Extension to malonate

  据报道，通过碱和硫促进的乙酸苯酯和查尔酮的环化，一种经济高效、实用、简单且可扩展的 α-吡喃酮合成方法。使用 dbu 作为碱催化剂，由起始组分原位生成迈克尔加合物，与 DABCO 和硫在 DMSO 中加热后，顺利氧化环化为 3,4,6-三芳基-2-吡喃酮。扩展为丙二酸酯代替乙酸苯酯得到4,6-二芳基-2-吡喃酮-2-羧酸酯。