8-甲氧基-2-苯基色原酮 | 26964-26-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 8-甲氧基-2-苯基色原酮
• 英文名称: 8-methoxyflavone
• 英文别名: 8-Methoxyflavon；8-methoxy-2-phenyl-4H-chromen-4-one；8-methoxy-2-phenylchromen-4-one
• CAS: 26964-26-1
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: FOXRKQWVTGRONY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  8-甲氧基-2-苯基色原酮 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到8-羟基黄酮
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Substituted Flavones as Gastroprotective Agents

  摘要：

  Flavone (1) was found to protect against ethanol-induced gastric damage in rats; however, it is known that certain compounds in the flavone class, including flavone itself, are inducers of hepatic drug metabolizing enzymes. With the hope of identifying gastroprotective flavones that have minimal effects on drug metabolizing enzymes, we have synthesized and evaluated selected flavone analogs. Gastroprotective potency in the ethanol model was retained by methoxy substitution in the 5-position (4) and by methoxy (12) or methyl (14) substitution in the 7-position. A number of substituted analogs of the potent molecule 5-methoxyflavone (4) were also synthesized, and in many cases, these substitutions provided gastroprotective molecules. In order to assess liver enzyme induction potential, two of the gastroprotective flavones, 7-methoxyflavone (12) and 5-methoxy-4'-fluoroflavone (26), were examined for their effect on liver microsomal cytochrome P450 and 7-ethoxyresorufin O-dealkylase (CYP1A) activity. These two compounds caused minimal changes in the cytochrome P450 concentration and were considerably less potent than beta-naphthoflavone as inducers of CYP1A enzyme activity. Furthermore, following oral administration to rats, 5-methoxy-4'-fluoroflavone (26) was found to protect against indomethacin-induced gastric damage. These results indicate that, through appropriate substitution, flavones can be obtained that are gastroprotective but have minimal effects on drug-metabolizing enzymes.

  DOI：

  10.1021/jm00025a011
• 作为产物：
  描述：

  2,3-二羟基苯乙酮 在 sodium benzoate 、 sodium carbonate 、 potassium carbonate 、 丙酮 作用下， 生成 8-甲氧基-2-苯基色原酮
  参考文献：
  名称：

  Ahluwalia et al., Proceedings - Indian Academy of Sciences, Section A, 1953, # 38, p. 480,490

  摘要：

  DOI：

文献信息

• Ru(<scp>ii</scp>)-Catalyzed C–H activation and annulation of salicylaldehydes with monosubstituted and disubstituted alkynes
  作者：Swagata Baruah、Partha Pratim Kaishap、Sanjib Gogoi

  DOI：10.1039/c6cc07204f

  日期：——

  The Ru(II)-catalyzed C-H activation and annulation reaction of salicylaldehydes and disubstituted alkynes affords chromones in high yields. This reaction works with terminal alkynes also and tolerates wide range of sensitive...

  Ru（II）催化的水杨醛与双取代炔烃的CH活化和环化反应可高产率地提供色酮。该反应还可与末端炔烃一起使用，并能耐受各种敏感的...
• Regioselective synthesis of flavone derivatives via DMAP-catalyzed cyclization of o-alkynoylphenols
  作者：Masahito Yoshida、Yuta Fujino、Koya Saito、Takayuki Doi

  DOI：10.1016/j.tet.2011.09.063

  日期：2011.12

  A catalytic amount of DMAP promoted cyclization of o-alkynoylphenols via a 6-endo cyclization mode leading to flavone derivatives in high yields without forming 5-exo cyclized aurone derivatives. Utilizing this method, methoxy substituted flavone and alkyl substituted γ-benzopyranone derivatives were synthesized.

  DMAP催化量的促进环化ö -alkynoylphenols经由6-内环化模式，导致高产量黄酮衍生物，而不形成5-外型环化噢哢衍生物。利用这种方法，合成了甲氧基取代的黄酮和烷基取代的γ-苯并吡喃酮衍生物。
• Rhodium(III)-catalyzed one-pot synthesis of flavonoids from salicylaldehydes and sulfoxonium ylides
  作者：Kang Cheng、Jinkang Chen、Licheng Jin、Jian Zhou、Xinpeng Jiang、Chuanming Yu

  DOI：10.1177/1747519819867230

  日期：2019.9

  Rh(III)-catalyzed C–H activation of salicylaldehyde followed by an insertion reaction with sulfoxonium ylides and cyclization is applied to the synthesis of flavonoids. This one-pot strategy exhibits good functional group tolerance and gives flavones in moderate-to-good yields.

  Rh(III) 催化的水杨醛的 C-H 活化，随后与锍叶立德的插入反应和环化作用用于合成黄酮类化合物。这种一锅法表现出良好的官能团耐受性，并以中等至良好的产量提供黄酮。
• Synthesis of 4<i>H</i>-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes
  作者：Yixia Yue、Jinsong Peng、Deqiang Wang、Yunyun Bian、Peng Sun、Chunxia Chen

  DOI：10.1021/acs.joc.7b00640

  日期：2017.5.19

  The palladium-catalyzed intramolecular acylation of alkenyl bromides and aldehydes was developed for an efficient synthesis of 4H-chromen-4-ones. With Pd(PPh3)4/Xphos as the catalyst and K2CO3 as the base, this protocol was applied to synthesize a small library of diversely functionalized flavonoids in moderate to good yields in 1,4-dioxane.

  开发了钯催化的烯基溴和醛的分子内酰化反应，以有效合成4 H -chromen-4-ones。以Pd（PPh 3）4 / Xphos为催化剂，以K 2 CO 3为碱，该方案被用于合成少量的，功能多样的黄酮类化合物，在1,4-二恶烷中的产率为中等。
• Reagent-free intramolecular hydrofunctionalization: a regioselective 6-<i>endo-dig</i> cyclization of <i>o</i>-alkynoylphenols
  作者：Chanhyun Jung、Siyuan Li、Kwanghee Lee、Mayavan Viji、Heesoon Lee、Soonsil Hyun、Kiho Lee、Young Kee Kang、Chhabi Lal Chaudhary、Jae-Kyung Jung

  DOI：10.1039/d1gc04848a

  日期：——

  Solvent-directed intramolecular hydrofunctionalization of readily available o-alkynoylphenols 1 was successfully achieved under reagent-free conditions. The hydrofunctionalization of 1 occurred by nucleophilic attack on the phenolic oxygen followed by consecutive migration of the phenolic H atom to the alkyne center, eventually affording γ-benzopyranones 2. The phenol O–H group forms intramolecular H-bonds

  在无试剂条件下成功实现了容易获得的邻炔基酚1的溶剂导向分子内氢官能化。1的氢官能化通过对酚氧的亲核攻击随后酚氢原子连续迁移到炔烃中心而发生，最终得到 γ-苯并吡喃酮2。酚 O-H 基团与羰基形成分子内 H 键，我们预测这些 H 键在极性溶剂存在下可以扭曲成它们最优选的构象。区域选择性 6 -endo-dig环化似乎在热力学上优于 5 -exo-dig循环化，由 DFT 计算支持。该策略之所以引人注目，是因为它无试剂、区域选择性、原子经济性高、原子、碳和反应质量效率高。

表征谱图