3-(4-methyloxybenzyl)-5,7-dimethoxychromen-4-one | 34811-77-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 3-(4-methyloxybenzyl)-5,7-dimethoxychromen-4-one
• 英文别名: 3-benzyl-5,7,4'-trimethoxychromanone；5,7-dimethoxy-3-(4-methoxy-benzyl)-chromen-4-one；5,7,4'-Trimethoxyhomoisoflavon；5,7-Dimethoxy-3-[(4-methoxyphenyl)methyl]chromen-4-one
• CAS: 34811-77-3
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: MROUWQSRATXRIH-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C
• 沸点：
  510.0±50.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methyloxybenzyl)-5,7-dimethoxychromen-4-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以83%的产率得到5,7-dimethoxy-3-(4-methoxybenzyl)chroman-4-one
  参考文献：
  名称：

  甲硅烷基醚的有机催化对映选择性质子化：范围，局限性和在制备富含对映异构体的黄酮类化合物中的应用

  摘要：

  在目前的工作中，据报道在各种质子亲核试剂作为质子源的情况下，通过多种手性氮碱作为催化剂，主要衍生自金鸡纳生物碱，对甲硅烷基烯醇醚进行对映选择性质子化。公开了对最相关的反应参数的详细研究，从而允许在温和和环境友好的条件下实现高达92％ee的高对映选择性和极佳的收率。此有机催化质子化的合成效用制备两个homoisoflavones期间展示图4a和4b中，从分离吊兰Inornatum和绵性厌食症，其分别用81％和78％ee的，获得的。

  DOI：

  10.1021/jo101585t
• 作为产物：
  描述：

  (E)-1-(2-羟基-4,6-二甲氧基苯基)-3-(4-甲氧基苯基)-2-丙烯-1-酮 在 palladium on activated charcoal 氢气 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 3-(4-methyloxybenzyl)-5,7-dimethoxychromen-4-one
  参考文献：
  名称：

  Synthe`se et activite´s angioprotectrice, anti-allergique et antihistaminique de benzyl-3 chromones (homo-isoflavones)

  摘要：

  DOI：

  10.1016/0223-5234(89)90060-3

文献信息

• New homoisoflavonoid analogues protect cells by regulating autophagy
  作者：Li-She Gan、Lin-Wei Zeng、Xiang-Rong Li、Chang-Xin Zhou、Jie Li

  DOI：10.1016/j.bmcl.2017.01.086

  日期：2017.3

  As a special group of naturally occurring flavonoids, homoisoflavonoids have been discovered as active components of several traditional Chinese medicines for nourishing heart and mind. In this study, twenty homoisoflavonoid analogues, including different substitution groups on rings A and B, as well as heteroaromatic B ring, were synthesized and evaluated for their cardioprotective and neuroprotective activities. In a H2O2-induced H9c2 cardiomyocytes injury assay, nine homoisoflavonoid analogues showed promising activities in the same level as the positive control, diazoxide. Six cardioprotective compounds with representative structure diversities were then evaluated for their neuroprotective effects on MPP+ induced SH-SY5Y cell injury model. Furthermore, autophagy inducing monodansylcadaverine (MDC) fluorescence staining methods and molecular docking studies indicated the action mechanism of these compounds may involve autophagy regulating via class I P13K signaling pathway. (C) 2017 Elsevier Ltd. All rights reserved.
• New Convenient Synthesis of Homoisoflavanones and (±)‐Di‐O‐methyldihydroeucomin
  作者：B. Serge Kirkiacharian、Michel Gomis

  DOI：10.1081/scc-200049789

  日期：2005.3

  Upon reaction of 1-(2-hydroxyphenyl)-3-phenylpropane-1-ones (2'-hydroxydihydrochalcones) with dimethylaminodimethoxymethane in boiling toluene, the corresponding 3-benzylchromones are obtained in excellent yields. These latter lead to 3-benzylchroman-4-ones (bomoisoflavanones) by catalytic hydrogenetion. These reactions were applied to the synthesis of (+/-)-3-benzylchroman-4-one and (+/-)-3(4-methoxybenzyl)-5,7-dimethoxychroman-4-one, (+/-)-di-O-methyldihydroeucomin.
• A highly enantioselective synthesis of (R)- and (S)-5,7-odimethyleucomol
  作者：Franklin A. Davis、Bang-Chi Chen

  DOI：10.1016/s0040-4039(00)97181-8

  日期：1990.1
• Jain, A. C.; Sharma, Anita; Srivastava, Rene, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 11, p. 1119 - 1121
  作者：Jain, A. C.、Sharma, Anita、Srivastava, Rene

  DOI：——

  日期：——
• KIRKIACHARIAN, SERGE;TONGO, HUBERT G.;BASTIDE, JANINE;BASTIDE, PIERRE;GRE+, EUR. J. MED. CHEM., 24,(1989) N, C. 541-546
  作者：KIRKIACHARIAN, SERGE、TONGO, HUBERT G.、BASTIDE, JANINE、BASTIDE, PIERRE、GRE+

  DOI：——

  日期：——