6-methylflavanone | 105166-60-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 6-methylflavanone
• 英文别名: 6-methyl-2-phenylchroman-4-one；6-Methylflavanon；6-methyl-2-phenyl-2,3-dihydrochromen-4-one
• CAS: 105166-60-7
• 化学式: C₁₆H₁₄O₂
• mdl: MFCD00823504
• 分子量: 238.286
• InChiKey: BTQWFEVKJXMNQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.187
• 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：

  6-methylflavanone 在 thallium(III) acetate 、 对甲苯磺酸 作用下， 以 various solvent(s) 为溶剂， 以92%的产率得到6-甲基-3-苯基色烯-4-酮
  参考文献：
  名称：

  th（III）-甲苯磺酸酯（TTS）=黄酮类化合物中黄酮类化合物的氧化性1,2-芳基重排=一种新的有用的异黄酮途径

  摘要：

  在丙腈中使用甲苯磺酸th （III）（由乙酸III（III）和-甲苯磺酸反应制得）对黄烷酮进行氧化可导致1,2-芳基转移，为异黄酮的合成提供了一条新的有用途径。

  DOI：

  10.1016/s0040-4039(00)94689-6
• 作为产物：
  描述：

  乙酸对甲酚酯 在 sodium hydroxide 、 三氯化铝 、 磷酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 48.75h， 生成 6-methylflavanone
  参考文献：
  名称：

  6-Methylflavanone, a more efficacious positive allosteric modulator of γ-aminobutyric acid (GABA) action at human recombinant α2β2γ2L than at α1β2γ2L and α1β2 GABAA receptors expressed in Xenopus oocytes

  摘要：

  6-Methylflavanone acted as a positive allosteric modulator of gamma-aminobutyric acid (GABA) responses at human recombinant alpha(1)beta(2)gamma(2L), alpha(1)beta(2)gamma(2L) and alpha(1)beta(2) GABA(A) receptors expressed in Xenopus laevis oocytes. It was essentially inactive at rho(1) GABA(C) receptors.The EC50 values for 6-methylflavanone for the positive modulation of the EC10-20 GABA responses were 22 mu M, 10 mu M and 6 mu M and the maximum potentiations were 120%, 417% and 130% at a alpha(1)beta(2)gamma(2L), alpha(1)beta(2)gamma(2L) and alpha(1)beta(2) GABA(A) receptors respectively.Thus 6-methylflavanone was much more efficacious as a positive modulator at alpha(1)beta(2)gamma(2L) than at alpha(1)beta(2)gamma(2L) and alpha(1)beta(2) GABA(A) receptors. This may be significant since diazepam-induced anxiolysis is considered to be mediated via alpha(2)-containing GABA(A) receptors, while sedation is thought to be mediated via alpha(1)-containing GABA(A) receptors.We have previously reported that 6-methylflavone (1-100 mu M) produced positive allosteric modulation at a alpha(1)beta(2)gamma(2L) and alpha(1)beta(2) GABA(A) receptors with no significant difference between the enhancement seen at either receptor subtype. In the present study, 6-methylflavone was tested at alpha(2)beta(2)gamma(2L) GABA(A) receptors and found to maximally potentiate the EC10-20 GABA response by 183 +/- 39% which is similar to that previously observed for 6-methylflavone at alpha(1)beta(2)gamma(2L) GABA(A) receptors. Thus, 6-methylflavone did not show a preference for alpha(2)beta(2)gamma(2L) over alpha(1)beta(1)gamma(2L) GABA(A) receptors in terms of efficacy.Compared to 6-methylflavone, 6-methylflavanone is more efficacious as a positive allosteric modulator at alpha(2)beta(2)gamma(2L) GABA(A) receptors, and less efficacious at alpha(1)beta(2)gamma(2L) GABA(A) receptors. This may represent a relatively unique type of selectivity for positive modulators of GABA-A receptor subtypes based on efficacy as distinct from potency.As was previously shown for 6-methylflavone at a alpha(1)beta(2)gamma(2L) GABA(A) receptors, the positive modulation of GABA responses at alpha(1)beta(2)gamma(2L) and alpha(2)beta(2)gamma(2L) GABA(A) receptors by 6-methylflavanone was insensitive to antagonism by flumazenil, indicating that this action is not mediated via "high-affinity" benzodiazepine sites. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2005.02.034

文献信息

• Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids
  作者：Hyung-Seok Yoo、Seung Hwan Son、Yang Yil Cho、Soo Jin Lee、Hyu Jeong Jang、Young Min Kim、Dong Hwan Kim、Nam Yong Kim、Boyoung Y. Park、Yong Sup Lee、Nam-Jung Kim

  DOI：10.1021/acs.joc.9b01162

  日期：2019.8.16

  total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92%.

  合宜地通过一锅二价的苯并二氢吡喃酮与芳基硼酸通过串联钯（II）催化合成了苯并二氢吡喃酮（一类具有化学未活化β位点的简单酮），合成了47种黄烷酮。该反应提供了一种以高达92％的收率获得各种黄烷酮（包括天然产物，如柚皮苷三甲醚）的新颖途径。
• Chemoselective Reduction of α,β-Unsaturated Aldehydes, Ketones, Carboxylic Acids, and Esters with Nickel Boride in Methanol–Water
  作者：Jitender Mohan Khurana、Purnima Sharma

  DOI：10.1246/bcsj.77.549

  日期：2004.3

  A facile procedure for the conjugate reduction of α,β-unsaturated aldehydes, ketones, carboxylic acids, and esters is reported with nickel boride generated in situ from NiCl2·6H2O/NaBH4 in methanol...

  据报道，使用由 NiCl2·6H2O/NaBH4 在甲醇中原位生成的硼化镍，可轻松共轭还原 α,β-不饱和醛、酮、羧酸和酯。
• Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/<i>oxa</i>-Michael Addition between Propargylamines with Water
  作者：Xinwei He、Mengqing Xie、Ruxue Li、Pui Ying Choy、Qiang Tang、Yongjia Shang、Fuk Yee Kwong

  DOI：10.1021/acs.orglett.0c01357

  日期：2020.6.5

  DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne–allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones

  已经开发了一种DBU催化的炔丙胺和水的一锅级联反应，用于合成黄烷酮。该过程是通过依次将水以1,4-共轭加成到炔基邻苯二甲酰甲基甲烷（o -AQM）上，然后进行炔烃-丙二烯异构化和随后的分子内氧杂-Michael加成反应。该策略提供了一种方便的方法，可以以良好的产率获得具有良好的官能团耐受性的宽泛的黄烷酮，特别是反应性卤素官能团。
• Tandem Fries Reaction–Conjugate Addition under Microwave Irradiation in Dry Media; One-pot Synthesis of Flavanones
  作者：Firouz Matloubi Moghaddam、Mohammad Ghaffarzadeh、Seyed Hossein Abdi-Oskoui

  DOI：10.1039/a902507c

  日期：——

  An AlCl3–ZnCl2 mixture supported on silica gel is found to be an efficient medium for the Fries rearrangement of acyloxybenzene or naphthalene derivatives in solvent-free conditions under microwave irradiation.

  发现载于硅胶上的AlCl 3 -ZnCl 2混合物是无溶剂条件下微波辐射下酰氧基苯或萘衍生物的Fries重排的有效介质。
• Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride
  作者：Motofumi Miura、Karin Shigematsu、Masaharu Toriyama、Shigeyasu Motohashi

  DOI：10.1016/j.tetlet.2021.153480

  日期：2021.11

  flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

  在温和条件下，从相应的羟基查耳酮与催化量的氟化铯水溶液通过氧杂-迈克尔加成容易合成总共 36 种黄烷酮，其中包括多环芳环和杂环。该方法可用于作为 SARS-CoV-2 刺突蛋白的已知强效抑制剂圣草酚的可扩展合成。