2-methyl-6-phenyl-4H-benzo[d][1,3]oxazin-4-one | 1237744-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-methyl-6-phenyl-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 2-Methyl-6-phenyl-3,1-benzoxazin-4-one
• CAS: 1237744-77-2
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: YAXGCEGKWYTPPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-6-phenyl-4H-benzo[d][1,3]oxazin-4-one 、 对氨基苯甲酸 在 溶剂黄146 作用下， 以40%的产率得到4-(2-methyl-4-oxo-6-phenylquinazolin-3(4H)-yl)benzoic acid
  参考文献：
  名称：

  Quinazolin-4-one Derivatives: A Novel Class of Noncompetitive NR2C/D Subunit-Selective N-Methyl-d-aspartate Receptor Antagonists

  摘要：

  We describe a new class of subunit-selective antagonists of N-methyl D-aspartate (NMDA)-selective ionotropic glutamate receptors that contain the (E)-3-phenyl-2-styrylquinazolin-4(3H)-one backbone. The inhibition of recombinant NMDA receptor function induced by these quinazolin-4-one derivatives is noncompetitive and voltage-independent, suggesting that this family of compounds does not exert action on the agonist binding site of the receptor or block the channel pore. The compounds described here resemble CP-465,022 ((S)-3-(2-chlorophenyl)-2-[2-(6-diethylaminomethyl-pyridin-2-yl)-vinyl]-6-fluoro-3H-quinazolin-4-one), a noncompetitive antagonist of AMPA-selective glutamate receptors. However, modification of ring substituents resulted in analogues with greater than 100-fold selectivity for recombinant NMDA receptors over AMPA and kainate receptors. Furthermore, within this series of compounds, analogues were identified with 50-fold selectivity for recombinant NR2C/D-containing receptors over NR2A/B containing receptors. These compounds represent a new class of noncompetitive subunit-selective NMDA receptor antagonists.

  DOI：

  10.1021/jm100027p
• 作为产物：
  描述：

  4'-氨基-联苯-3-羧酸 、 乙酸酐 以65%的产率得到2-methyl-6-phenyl-4H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  Quinazolin-4-one Derivatives: A Novel Class of Noncompetitive NR2C/D Subunit-Selective N-Methyl-d-aspartate Receptor Antagonists

  摘要：

  We describe a new class of subunit-selective antagonists of N-methyl D-aspartate (NMDA)-selective ionotropic glutamate receptors that contain the (E)-3-phenyl-2-styrylquinazolin-4(3H)-one backbone. The inhibition of recombinant NMDA receptor function induced by these quinazolin-4-one derivatives is noncompetitive and voltage-independent, suggesting that this family of compounds does not exert action on the agonist binding site of the receptor or block the channel pore. The compounds described here resemble CP-465,022 ((S)-3-(2-chlorophenyl)-2-[2-(6-diethylaminomethyl-pyridin-2-yl)-vinyl]-6-fluoro-3H-quinazolin-4-one), a noncompetitive antagonist of AMPA-selective glutamate receptors. However, modification of ring substituents resulted in analogues with greater than 100-fold selectivity for recombinant NMDA receptors over AMPA and kainate receptors. Furthermore, within this series of compounds, analogues were identified with 50-fold selectivity for recombinant NR2C/D-containing receptors over NR2A/B containing receptors. These compounds represent a new class of noncompetitive subunit-selective NMDA receptor antagonists.

  DOI：

  10.1021/jm100027p

文献信息

• Heterocyclic Compound
  申请人：Amasaki Ichiro

  公开号：US20100004439A1

  公开（公告）日：2010-01-07

  A compound represented by the following Formula (1): wherein, Het 1 represents a bivalent five- or six-membered aromatic heterocyclic residue and may further be substituted; X a to X d each independently represent a heteroatom and may further be substituted; Y a to Y f each independently represent a heteroatom or a carbon atom and may further be substituted; the ring bound to Het 1 may have a double bond at any position

  以下是您提供的化学公式(1)的中文翻译： 其中，Het1代表一个二价的五元或六元芳香杂环基团，且可以进一步被取代；Xa至Xd每个独立地代表一个杂原子，且可以进一步被取代；Ya至Yf每个独立地代表一个杂原子或一个碳原子，且可以进一步被取代；与Het1相连的环可以在任何位置有一个双键。
• Construction of Benzoxazinones from Anilines and Their Derivatives
  作者：Teng-Fei Zhao、Xiao-Li Xu、Wei-Yin Sun、Yi Lu

  DOI：10.1021/acs.orglett.3c01511

  日期：2023.7.14

  Herein we report a strategy concerning Rh(III)-catalyzed direct ortho-C–H bond carbonylation to construct benzoxazinones from anilines and their derivatives with high atom economy. Interestingly, the corresponding amides were generated in situ from anilines when excess Ac2O was added and directed the following C–H bond carbonylation to form benzoxazinones. Extensive functional group tolerance can be

  在此，我们报道了一种Rh(III)催化的直接邻-C-H键羰基化反应，以苯胺及其高原子经济性衍生物构建苯并恶嗪酮的策略。有趣的是，当添加过量的Ac 2 O时，苯胺原位生成相应的酰胺，并引导随后的C-H键羰基化形成苯并恶嗪酮。当安装烷基酰胺导向基团时，可以实现广泛的官能团耐受性。此外，该方法可以方便地对一些带有芳胺基团的药物进行衍生化，显示出其潜在的应用前景。
• RESIN MOLDED PRODUCT AND POLYMER FILM
  申请人：FUJIFILM Corporation

  公开号：EP2270076A1

  公开（公告）日：2011-01-05

  A formed resin article, containing a compound and a polymer substance, wherein the compound has a maximum absorption wavelength in a range of 400 nm or less, measured in a solution of the compound, wherein the compound is contained in the polymer substance in a quantity of 5 g/m2 or less, and wherein a light transmittance of the article at a wavelength of 410 nm is 5% or less.

  一种成型树脂制品，含有一种化合物和一种高分子物质，其中化合物在其溶液中的最大吸收波长为 400 纳米或以下、 其中化合物在聚合物物质中的含量为 5 克/平方米或更少，以及 在波长为 410 纳米时，物品的透光率为 5%或更低。
• ULTRAVIOLET ABSORBENT COMPOSITIONS
  申请人：FUJIFILM Corporation

  公开号：EP2270113A1

  公开（公告）日：2011-01-05

  An ultraviolet absorbent composition, comprising: at least one kind of ultraviolet absorbent (A) that is a compound represented by the following Formula (1); and at least one kind of ultraviolet absorbent (B) that is a compound where absorbance at 320 nm is 20% or more of absorbance at absorption maximum wavelength in the range of from 270 nm to 400 nm and the absorption maximum wavelength is 380 nm or less: wherein Het1 represents a bivalent five- or six-membered aromatic heterocyclic residue; the aromatic heterocyclic residue may have a substituent; Xa, Xb, Xc and Xd each independently represent a heteroatom; Xa to Xd may have a substituent; Ya, Yb, Yc, Yd, Ye and Yf each independently represent a heteroatom or a carbon atom; Ya to Yf may have a substituent; and the rings bound to Het1 may have a double bond at any position.

  一种紫外线吸收剂组合物，包括 至少一种紫外线吸收剂（A），它是由下式（1）表示的化合物；以及 至少一种紫外线吸收剂 (B)，该化合物在 320 纳米波长处的吸光度为 270 纳米至 400 纳米波长范围内吸收最大波长处吸光度的 20% 或以上，且吸收最大波长为 380 纳米或以下： 其中 Het1 代表二价五元或六元芳香杂环残基；芳香杂环残基可具有取代基； Xa、Xb、Xc 和 Xd 各自独立地代表一个杂原子；Xa 至 Xd 可具有一个取代基； Ya、Yb、Yc、Yd、Ye 和 Yf 各自独立地代表一个杂原子或一个碳原子；Ya 至 Yf 可具有一个取代基；以及 与 Het1 结合的环可以在任何位置具有双键。
• Ultraviolet Absorbent and Heterocyclic Compound
  申请人：Amasaki Ichiro

  公开号：US20090239982A1

  公开（公告）日：2009-09-24

  An ultraviolet absorbent represented by the following Formula (1) or (6): wherein, Het 1 represents a monovalent five- or six-membered aromatic heterocyclic residue; X a and X b each independently represent a heteroatom; Y a to Y c each independently represent a heteroatom or a carbon atom; the ring formed from carbon atom, X a , X b , Y a to Y c may have a double bond at any position and has at least one fused ring; wherein, Het 6 represents a monovalent five- or six-membered aromatic heterocyclic residue; X 6a and X 6b each independently represent a heteroatom; Y 6a , Y 6b and Y 6c each independently represent a heteroatom or a carbon atom; L 6 represents a bi- to octa-valent connecting group; n is an integer of 2 or more, and m is an integer of 0 or more.