6-(2,4-dimethoxycinnamoyl)-7-hydroxy-2,2-dimethyldihydrobenzo[1,2-b]pyran | 148180-71-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 6-(2,4-dimethoxycinnamoyl)-7-hydroxy-2,2-dimethyldihydrobenzo[1,2-b]pyran
• 英文别名: 2'-hydroxy-2,4-dimethoxy-6",6"-dimethyl-4",5"-dihydropyrano<2",3":4',5'>chalcone；2,2-Dimethyl-7-hydroxy-6-(2,4-dimethoxycinnamoyl)chromane；(E)-3-(2,4-dimethoxyphenyl)-1-(7-hydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)prop-2-en-1-one
• CAS: 148180-71-6
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: IGHWDGIJKSBFBA-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(2,4-dimethoxycinnamoyl)-7-hydroxy-2,2-dimethyldihydrobenzo[1,2-b]pyran 在 吡啶 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 2-(2,4-Dimethoxy-phenyl)-8,8-dimethyl-2,3,7,8-tetrahydro-6H-pyrano[3,2-g]chromen-4-one
  参考文献：
  名称：

  Parmar, V. S.; Vardhan, Anand; Sharma, S. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 1, p. 17 - 26

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(7-hydroxy-2,2-dimethylchroman-6-yl)ethanone 、 2,4-二甲氧基苯甲醛 在 barium dihydroxide 作用下， 生成 6-(2,4-dimethoxycinnamoyl)-7-hydroxy-2,2-dimethyldihydrobenzo[1,2-b]pyran
  参考文献：
  名称：

  13C nuclear magnetic resonance studies on pyrano- and dihydropyrano-1,3- diphenylprop-2-enones

  摘要：

  记录了 19 种不同取代的吡喃-和二氢吡喃-1,3-二苯基丙-2-烯酮的 13C NMR 谱，并对结果进行了讨论。这些数据将有助于鉴定新的天然查耳酮。

  DOI：

  10.1002/mrc.1260300619

文献信息

• Anti-Invasive Activity of 3,7-Dimethoxyflavonein Vitro
  作者：Virinder S. Parmar、Rajni Jain、Sunil K. Sharma、Anand Vardhan、Amitabh Jha、Poonam Taneja、Suddham Singh、Barbara M. Vyncke、Marc E. Bracke、Marc M. Mareel

  DOI：10.1002/jps.2600830906

  日期：1994.9

  compounds, belonging to the flavonoids, chalcones, or coumarins, was tested in this assay for invasion. The anti-invasive activity of 3,7-dimethoxyflavone was found at concentrations ranging from 1 to 100 microM. At these anti-invasive concentrations, no cytotoxic effects could be detected: the anti-invasive effect was reversible upon omission of the molecule from the medium, and treatment of MCF-7/6 cells

  在器官培养物中，研究了MCF-7 / 6人乳腺癌细胞侵袭胚胎鸡心脏碎片的过程，历时8天。在此测定法中测试了31种多酚化合物的作用，这些化合物属于类黄酮，查耳酮或香豆素，具有抗侵袭性。发现3,7-二甲氧基黄酮的抗侵袭活性的浓度范围为1至100 microM。在这些抗侵袭浓度下，未检测到细胞毒性作用：从培养基中省略分子后，抗侵袭作用是可逆的，并且MCF-7 / 6细胞或心脏碎片的处理不会影响随后的外植体生长。组织培养塑料。该分子既不抑制MCF-7 / 6细胞聚集体的生长，也不抑制悬浮培养中保存的心脏片段的生长。3，作用机理
• New fragmentation pathways in the electron impact mass spectrometry of derivatized pyrano-1,3-diphenylprop-2-enones
  作者：Virinder S. Parmar、Sunil K. Sharma、Anand Vardhan、Rakesh K. Sharma、Jørgen Møller、Per M. Boll

  DOI：10.1002/oms.1210280106

  日期：1993.1

  AbstractThe fragmentation patterns of closely related chalcones, cinnamoylchromans and cinnamoylchromenes, are reported to be strikingly different. The mass spectra of the first group show peaks typical of the fragmentation of simple chalcones balanced by additional fragmentation routes competing effectively with the typical chalcone fragmentation. For the other group with the introduced double bond the fragmentation is considerably changed. Initial loss of a methyl group gives rise to formation of the base peak in three of four examples. The [M – CH3]+ ion decomposes further, eliminating a styrene yielding the m/z 187 ion. This process may be rationalized as a retro‐Diels–Alder fragmentation of a flavanone formed on intramolecular rearrangement of the molecular ion.