4-吗啉基-1,2-萘醌 | 4569-83-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-吗啉基-1,2-萘醌
• 英文名称: 4-morpholinonaphthalene-1,2-dione
• 英文别名: 4-morpholino-1,2-naphthoquinone；4-morpholin-4-yl-[1,2]naphthoquinone；4-morpholino-[1,2]naphthoquinone；4-Morpholino-[1,2]naphthochinon；4-morpholin-4-ylnaphthalene-1,2-dione；1,2-naphthoquinone-4-morpholine
• CAS: 4569-83-9
• 化学式: C₁₄H₁₃NO₃
• mdl: MFCD01306263
• 分子量: 243.262
• InChiKey: CGVPOLUKPMAOAN-UHFFFAOYSA-N

物化性质

• 熔点：
  199-200 °C
• 沸点：
  422.5±45.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-吗啉基-1,2-萘醌 生成 2-羟基-1,4-萘醌
  参考文献：
  名称：

  Reaction of 1,2-naphthoquinone-4-sulfonate with aliphatic amines: Structure of the colored products and kinetics.

  摘要：

  将钠1,2-萘醌-4-磺酸盐(I)中的4-磺酸基替换成多种脂肪胺(II)，得到有色的4-取代的1,2-萘醌(Q)：4-吗啉代-Q(IIIa)、4-哌啶代-Q(IIIb)、4-吡咯烷代-Q(IIIc)、4-(1,2,4-三唑-1-基)-Q(IIId)、4-(2-吡咯基)-Q(IIIe)、4-二甲氨基-Q(IIIf)、4-二乙氨基-Q(IIIg)、4-异丙氨基-Q(IIIh)及4-(4-氨基-2-甲基-5-嘧啶基甲氨基)-Q(IIIi)。被取代的亚硫酸盐迅速加到I的4位上，形成一种无色的副产物，即二钠2-羟基-1-氧-1,4-二氢-4,4-萘二磺酸盐(IV)。反应速率是通过极谱法测量的。IIIa和IV的生成是连续的二级反应。速率常数的pH曲线在pH10处有一个圆顶峰，这说明自由基(II)在邻醌形式(I)的4-碳位上发生了亲核取代反应。IIIa水解成2-羟基-1,4-萘醌(V)是一个酸碱催化的假一级反应。通过研究找到了用光度法测定吗啉(IIa)的最优条件，即IIa与过量的I在pH8和25摄氏度下反应30分钟。

  DOI：

  10.1248/cpb.32.3093
• 作为产物：
  描述：

  萘酚 在 甲醇 、 氧气 、 copper diacetate 作用下， 生成 4-吗啉基-1,2-萘醌
  参考文献：
  名称：

  Brackman; Havinga, Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 937,950

  摘要：

  DOI：

文献信息

• Novel pyrazino-phenanthroline based rigid donor-π-acceptor compounds: A detail study of optical properties, acidochromism, solvatochromism and structure-property relationship
  作者：Shantaram Kothavale、Nagaiyan Sekar

  DOI：10.1016/j.dyepig.2016.08.032

  日期：2017.1

  Donor-π-acceptor-π-auxiliary acceptor type compounds have been designed and synthesized to study their rigidity and structural effects on optical properties. Structural variation is achieved by changing the central π-conjugated core with naphthalene, acenaphthene and phenanthrene based donor-π-acceptor compounds containing N, N-diethyl aniline or morpholine as donor and pyrazine ring fused with phenanthroline

  设计并合成了供体-π-受体-π-辅助受体类型的化合物，以研究其刚性和结构对光学性质的影响。结构变化是通过用含有N，N的萘，和菲基供体-π受体化合物改变中心π-共轭核来实现的-二乙基苯胺或吗啉为供体，吡嗪环与菲咯啉为受体稠合。进行了正负酸致变色的详细研究。Lippert-Mataga，Mac-Rae和Reichardt相关性阐明了这些化合物的分子内电荷转移，溶剂变色和高极性激发态。还执行了使用Kamlet-Taft和加泰罗尼亚语参数的多线性回归分析，以支持在从非极性溶剂到极性溶剂的吸收和发射光谱中观察到的溶剂变色现象。所有光谱结果均通过密度泛函理论（DFT）计算从理论上进行关联。
• New compounds with antiglutamatergic properties and uses thereof
  申请人：Faust Pharmaceuticals

  公开号：EP1961738A1

  公开（公告）日：2008-08-27

  The present invention provides new compounds displaying antiglutamatergic properties. It also provides the use of such compounds for the treatment and/or prophylaxis of conditions and diseases linked to abnormalities in glutamatergic transmission. It further provides a pharmaceutical composition for the treatment and/or prophylaxis of acute and chronic neurodegenerative conditions and disorders.

  本发明提供了显示抗谷氨酸作用的新化合物。它还提供了利用这些化合物治疗和/或预防与谷氨酸传递异常相关的疾病和疾病的用途。此外，还提供了用于治疗和/或预防急性和慢性神经退行性疾病和疾病的药物组合物。
• Synthesis and Optical Properties of Acidochromic Amine-Substituted Benzo[<i>a</i>]phenazines
  作者：Prachi Singh、Abhishek Baheti、K. R. Justin Thomas

  DOI：10.1021/jo200857p

  日期：2011.8.5

  transition between the amine and pyrazine segments and benzo[a]phenazine localized π–π* transitions. Although the absorption spectra of the dyes were not significantly influenced by the nature of the solvents, addition of TFA led to a prominent red-shift in the absorption spectra owing to the protonation at the quinoxaline segment which enhanced the electron-accepting ability. The qualitative trends

  通过使用简单的连续迈克尔型与各种伯胺和仲胺的顺序加成反应以及所得胺取代的缩合反应，由1,2-萘醌合成了一系列新的烷基胺或芳胺取代的苯并[ a ]吩嗪类化合物。 1,2-萘醌与邻苯二胺。它们显示出吸收峰，该吸收峰源于胺和吡嗪链段与苯并[ a]之间的电荷转移跃迁。] phenazine局部化了π–π *跃迁。尽管染料的吸收光谱不受溶剂性质的影响，但由于喹喔啉段的质子化提高了电子接受能力，TFA的加入导致吸收光谱显着的红移。密度泛函理论计算支持了光学性质和酸致变色现象的定性趋势。染料在发射光谱中显示出正溶剂溶变色，表明存在更多极性的激发态。染料的特征还在于源自吡嗪链段的准可逆还原对，其经历了与胺链段的供电子强度相对应的变化。
• Novel Fluorescent Phenazines : Synthesis, Characterization, Photophysical Properties and DFT Calculations
  作者：Abhinav B. Tathe、Nagaiyan Sekar

  DOI：10.1007/s10895-015-1631-0

  日期：2015.9

  The organic compounds with donor-π-bridge-acceptor type of architecture are of great interest for application as semiconductors. The synthesized compounds are obtained from 4-morpholino naphthalene-1,2-dione and 4-(4-(diethylamino) phenyl)naphthalene-1,2-dione and mono substituted ortho-phenylene diamines by condensation reaction. The donor groups are morpholinyl and N,N-diethylamino phenyl moieties, whereas acceptors are substituted phenazines. The synthesized molecules were characterized by spectral analysis.. The effect of the substitution has been studied on the basis of photophysical properties of the molecules. The halochromism behaviour of the molecule shows that at low to moderate acidity they respond differently with two types of donors. DFT computations were used in conjunction with NMR analysis to determine the ratio of the positional isomers.

  具有供体-π桥-受体结构类型的有机化合物在用作半导体方面具有重大意义。这些合成化合物是由 4-吗啉基萘-1,2-二酮和 4-(4-(二乙基氨基)苯基)萘-1,2-二酮以及单取代邻苯二胺通过缩合反应得到的。供体为吗啉基和 N,N-二乙氨基苯基，受体为取代的吩嗪。合成的分子通过光谱分析进行了表征。根据分子的光物理特性研究了取代的影响。分子的卤色行为表明，在中低酸度条件下，它们对两种供体的反应是不同的。DFT 计算与 NMR 分析相结合，确定了位置异构体的比例。
• Photochromic articles
  申请人：PILKINGTON PLC

  公开号：EP0245020A2

  公开（公告）日：1987-11-11

  A plastic organic photochromic article, typically a lens such as an ophthalmic lens or a window such as a vehicle roof light, comprising a plastics host material having a photochromic compound incorporated therein or applied thereto, the article being characterised in that it exhibits the following properties, measured at Air Mass 2 at 25 °C: (a) an integrated visible transmission in the faded state (B.IVT) ranging from 90 to 25 %, (b) an integrated visible transmission in the darkened state (D.IVT) ranging from 1 to 50 %, preferably 4 to 30 %, (c) the rate of darkening of the article when it is exposed to actinic radiation is such that 88% of the darkening range is achieved in 30 seconds or less, i.e.TB8 30 secs, (d) the rate of fading of the article from its fully darkened condition is such that more than 60 % of the optical density range is recovered in 60 seconds, i.e. % ODG-1 60%, and (e) the induced optical density of the article, i.e. the change in the optical density of the article, in moving from the faded state (B.IVT) to the darkened state (D.IVT), is greater than 0.45. Typically, the photochromic compound is a spiro-oxazine compound of general formula (II),

  一种塑料有机光致变色制品，通常是镜片（如眼科镜片）或车窗（如车顶灯），由塑料主材料组成，塑料主材料中含有或涂有光致变色化合物： (a) 在褪色状态下的综合可见光透射率（B.IVT）从 90%到 25%不等、 (b) 变暗状态下的综合可见透射率（D.IVT）为 1-50%，最好为 4-30%、 (c) 当物品暴露在光辐射下时，其变黑的速度能在 30 秒或更短时间内达到变黑范围的 88%，即 TB8 30 秒、 (d) 物品从完全变暗状态开始褪色的速度为 60 秒内恢复 60%以上的光密度范 围，即 % ODG-1 60%，以及 (e) 物品的诱导光密度，即物品从褪色状态（B.IVT）到变暗状态（D.IVT）的光密度变化大于 0.45。 典型的光致变色化合物是通式（II）的螺嗪化合物、

表征谱图