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7,8-二甲基-10-甲酰基甲基异咯嗪 | 4250-90-2

分子结构分类

有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物

中文名称

7,8-二甲基-10-甲酰基甲基异咯嗪

中文别名

——

英文名称

Formylmethylflavin

英文别名

7,8-dimethyl-10-(formylmethyl)isoalloxazine；7,8-dimethyl-10-acetaldehyde isoalloxazine；6,7-Dimethyl-9-formylmethyl-isoalloxazin；7,8-Dimethyl-10-formylmethylisoalloxazine；2-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)acetaldehyde

CAS

4250-90-2

化学式

C₁₄H₁₂N₄O₃

mdl

——

分子量

284.274

InChiKey

AUZWNAFEXXLJDA-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

0.6
重原子数：

21
可旋转键数：

2
环数：

3.0
sp3杂化的碳原子比例：

0.21
拓扑面积：

91.2
氢给体数：

1
氢受体数：

4

安全信息

海关编码：

2933990090

SDS

SDS：4151c3e6d4434e31a3cdab8efe6513a8

查看

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	Hydroxyethylflavin	3180-56-1	C₁₄H₁₄N₄O₃	286.29
——	10-(2,2-dihydroxylethyl)-7,8-dimethylisoalloxazine	825630-94-2	C₁₄H₁₄N₄O₄	302.29
维生素 B2	riboflavin	83-88-5	C₁₇H₂₀N₄O₆	376.369
——	riboflavin	——	C₁₇H₂₀N₄O₆	376.369
2,6-蒽二酚	Flavin mononucleotide	146-17-8	C₁₇H₂₁N₄O₉P	456.349
腺嘌呤黄素	flavin adenine dinucleotide	146-14-5	C₂₇H₃₃N₉O₁₅P₂	785.558

下游产品

中文名称	英文名称	CAS号	化学式	分子量
羧甲基黄素	carboxymethylflavin	21079-31-2	C₁₄H₁₂N₄O₄	300.274
——	Hydroxyethylflavin	3180-56-1	C₁₄H₁₄N₄O₃	286.29
——	10-(2,2-dihydroxylethyl)-7,8-dimethylisoalloxazine	825630-94-2	C₁₄H₁₄N₄O₄	302.29
——	10-(2-(3-aminopropylamino)ethyl)-7,8-dimethylbenzo[g]pteridine-2,4(3H,10H)-dione	1207984-30-2	C₁₇H₂₂N₆O₂	342.401
——	{3-[2-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)acetylamino]propyl}phosphonic acid	1207984-20-0	C₁₇H₂₀N₅O₆P	421.349
——	10-(2-(benzylamino)ethyl)-7,8-dimethylbenzo[g]pteridine-2,4(3H,10H)-dione	——	C₂₁H₂₁N₅O₂	375.43
——	{[2-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)ethyl]methylamino}acetic acid	1207984-14-2	C₁₇H₁₉N₅O₄	357.369
——	N-(4-chlorobenzyl)-2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)acetamide	1262314-97-5	C₂₁H₁₈ClN₅O₃	423.859
——	(S)-2-amino-6-[2-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)ethylamino]hexanoic acid	1207984-15-3	C₂₀H₂₆N₆O₄	414.464
光黃素	lumiflavin	1088-56-8	C₁₃H₁₂N₄O₂	256.264
——	N-(4-((2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethyl)amino)phenyl)acetamide	1262314-94-2	C₂₂H₂₂N₆O₃	418.455
——	1-[2-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-acetyl]-piperidine-4-carboxylic acid	1262314-60-2	C₂₀H₂₁N₅O₅	411.417
——	diethyl 2-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)acetamido)ethylphosphonate	1207983-76-3	C₂₀H₂₆N₅O₆P	463.43
——	N-(3-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylamino)propyl)-1,1,1-trifluoromethanesulfonamide	1207983-49-0	C₁₈H₂₁F₃N₆O₄S	474.464
——	{3-[2-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)acetylamino]propyl}phosphonic acid diethyl ester	1207984-21-1	C₂₁H₂₈N₅O₆P	477.457
——	10-(2-(3,4-dichIorobenzylamino)ethyl)-7,8-dimethyIbenzo[g]pteridine-2,4(3H,10H)-dione	1207984-64-2	C₂₁H₁₉Cl₂N₅O₂	444.32
——	1-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-ethyl)-piperidine-4-carboxylic acid	1262314-79-3	C₂₀H₂₃N₅O₄	397.434
——	4-((2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylamino)methyl)benzoic acid	1207984-31-3	C₂₂H₂₁N₅O₄	419.44
——	N-(3-(bis(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethyl)amino)propyl)-1,1,1-trifluoromethanesulfonamide	1207983-51-4	C₃₂H₃₃F₃N₁₀O₆S	742.739
——	1-[2-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)-acetyl]-piperidine-4-carboxylic acid tert-butyl ester	1262315-29-6	C₂₄H₂₉N₅O₅	467.525
——	((1-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethyl)piperidin-4-yl)methyl)carbamamic acid tert-butyl ester	1262315-27-4	C₂₅H₃₄N₆O₄	482.583
——	(S)-1-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethyl)pyrrolidine-2-carboxylic acid	1262314-70-4	C₁₉H₂₁N₅O₄	383.407
——	(S)-2-tert-butoxycarbonylamino-6-[2-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)ethylamino]hexanoic acid	1207984-16-4	C₂₅H₃₄N₆O₆	514.582
——	2-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylamino)benzoic acid	1207984-12-0	C₂₁H₁₉N₅O₄	405.413
——	2-[2-(7,8-dimethyl-2,4-dioxo-3,4-dihydro-2H-benzo[g]pteridin-10-yl)ethylamino]pentanedioic acid di-tert-butyl ester	1207984-17-5	C₂₇H₃₇N₅O₆	527.621
——	((2-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)acetamido)ethyl)phosphoryl)bis(oxy)bis(methylene) bis(2,2-dimethylpropanoate)	1207983-74-1	C₂₈H₃₈N₅O₁₀P	635.611
——	tert-butyl 2-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylamino)benzoate	1207984-13-1	C₂₅H₂₇N₅O₄	461.52
——	tert-butyl 3,4-dichlorobenzyl(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethyl)carbamate	1207984-66-4	C₂₆H₂₇Cl₂N₅O₄	544.437
——	(S)-1-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethyl)-N-(methylsulfonyl)pyrrolidine-2-carboxamide	1262314-62-4	C₂₀H₂₄N₆O₅S	460.514
——	(R)-1-(2-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethyl)-N-(methylsulfonyl)pyrrolidine-2-carboxamide	1262314-63-5	C₂₀H₂₄N₆O₅S	460.514

反应信息

作为反应物：

描述：

7,8-二甲基-10-甲酰基甲基异咯嗪在 sodium chlorite 、 sodium dihydrogenphosphate 、 3-甲基-1-环己烯作用下，以水、乙腈、叔丁醇为溶剂，以68%的产率得到羧甲基黄素

参考文献：

名称：

[EN] FLAVIN DERIVATIVES
[FR] DÉRIVÉS DES FLAVINES

摘要：

本发明涉及新型黄素衍生物和其他黄素衍生物，它们的用途和用作核糖开关配体和/或抗感染剂的组合物。该发明还提供了制备新型黄素衍生物的方法。

公开号：

WO2011008247A1
作为产物：

描述：

2,6-蒽二酚在氧气作用下，反应 0.08h，生成 7,8-二甲基-10-甲酰基甲基异咯嗪

参考文献：

名称：

Photoirradiation products of flavin derivatives, and the effects of photooxidation on guanine

摘要：

Photoirradiation in the presence of riboflavin led to guanine oxidation and the formation of imidazolone. Meanwhile, riboflavin itself was degraded by ultraviolet light A (UV-A) and visible light (VIS) radiation, and the end product was lumichrome. VIS radiation in the presence of riboflavin oxidized guanine similarly to UV-A radiation. Although UV-A radiation with lumichrome oxidized guanine, VIS radiation with lumichrome did not. Thus, UV-A radiation with riboflavin can oxidize guanine even if riboflavin is degraded to lumichrome. In contrast, following VIS radiation degradation of riboflavin to lumichrome, VIS radiation with riboflavin is hardly capable of oxidizing guanine. The consequences of riboflavin degradation and guanine photooxidation can be extended to flavin mononucleotide and flavin adenine dinucleotide. In addition, we report advanced synthesis; carboxymethylflavin was obtained by oxidation of formylmethylflavin with chlorite and hydrogen peroxide; lumichrome was obtained by heating of formylmethylflavin in 50% AcOH; lumiflavin was obtained by incubation of formylmethylflavin in 2 M NaOH, followed by isolation by step-by-step concentration. (C) 2009 Elsevier Ltd. All rights reserved.

DOI：

10.1016/j.bmcl.2009.01.112

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文献信息

[EN] FLAVIN DERIVATIVES<br/>[FR] DÉRIVÉS DE LA FLAVINE

申请人：BIORELIX PHARMACEUTICALS INC

公开号：WO2010019208A1

公开（公告）日：2010-02-18

The present invention relates novel flavin derivatives and other flavin derivatives, their use and compositions for use as riboswitch ligands and/or anti-infectives. The invention also provides method of making novel flavin derivatives.

本发明涉及新型黄素衍生物和其他黄素衍生物，它们的用途以及用作核糖开关配体和/或抗感染剂的组合物。该发明还提供了制备新型黄素衍生物的方法。
Flavin-catalyzed aerobic oxidation of sulfides and thiols with formic acid/triethylamine

作者：Shun-Ichi Murahashi、Dazhi Zhang、Hiroki Iida、Toshio Miyawaki、Masaaki Uenaka、Kenji Murano、Kanji Meguro

DOI：10.1039/c4cc05216a

日期：——

An efficient and practical method for flavin-catalyzed aerobic oxidation of sulfides and thiols with formic acid/TEA is described.

一种高效实用的方法，用于利用呋喕催化的氧化硫醚和硫醇，使用甲酸/三乙胺。
用于蓝光受体光致电子转移研究的模型化合物及其制备方法

申请人：中国人民解放军国防科学技术大学

公开号：CN104496992B

公开（公告）日：2016-06-29

本发明公开了一种用于蓝光受体光致电子转移研究的模型化合物及其制备方法。该模型化合物具有如式(Ⅰ)所示的结构通式，n为≥1的整数。制备方法包括依次制备端-(N-苄氧羰基)脂肪酸、2-(端-(N-苄氧羰基)脂肪酰胺基)-3-(1H-吲哚基-3)丙酸甲酯、2-(端-氨基脂肪酰胺基)-3-(1H-吲哚基-3)丙酸甲酯、7,8-二甲基-10-乙醛基-异咯嗪和用于蓝光受体光致电子转移研究的模型化合物。本发明的模型化合物以黄素作为光敏剂，以适当长度的间隔臂分子通过共价键与作为电子给体的色氨酸连接，制备方法路线短、成本低、简单方便、收率高。
Efficient Use of Photons in Photoredox/Enamine Dual Catalysis with a Peptide-Bridged Flavin–Amine Hybrid

作者：Takuma Tagami、Yukihiro Arakawa、Keiji Minagawa、Yasushi Imada

DOI：10.1021/acs.orglett.9b02567

日期：2019.9.6

short peptide linker with the aim of using photons as efficiently as possible in photoredox/enamine dual catalysis. We herein report a peptide-bridged flavin-amine hybrid that can catalyze α-oxyamination of aldehydes with TEMPO under weak blue light irradiation to achieve an extremely high quantum yield of reaction (Φ = 0.80).

异短恶嗪（黄素）环系统和仲胺已通过短肽接头整合在一起，目的是在光氧化还原/烯胺双重催化中尽可能有效地利用光子。我们在本文中报道了一种肽桥联的黄素-胺杂化物，该杂化物可以在弱蓝光照射下用TEMPO催化醛的α-氧化胺化反应，以实现极高的反应量子产率（Φ= 0.80）。
Effect of Caffeine Complexation on the Photolysis of Riboflavin in Aqueous Solution: A Kinetic Study

作者：Iqbal Ahmad、Sofia Ahmed、Muhammad Ali Sheraz、Muhammad Aminuddin、Faiyaz Hussain Madni Vaid

DOI：10.1248/cpb.57.1363

日期：——

The effect of caffeine complexation with riboflavin on the kinetics of riboflavin photolysis in the pH range 2.0-10.5 has been studied. The photolysis of riboflavin solutions (5x10(-5) M) was carried out in the presence of caffeine (0.5-2.5x10(-4) M) using a visible radiation source. A specific multicomponent spectrophotometric method was used for the determination of riboflavin and photoproducts in

研究了咖啡因与核黄素络合对核黄素在2.0-10.5范围内光解动力学的影响。核黄素溶液（5x10（-5）M）的光解是在咖啡因（0.5-2.5x10（-4）M）存在下使用可见辐射源进行的。使用特定的多组分分光光度法测定光解溶液中的核黄素和光产物。光解反应的表观一级速率常数（k）为2.71x10（-4）至4.26x10（-2）min（-1）。速率常数的值随咖啡因浓度的增加而降低，表明其对反应的抑制作用。咖啡因抑制反应的二级速率常数（k'）在0.13至5.10x10（-3）M（-1）min（-1）范围内。在各种咖啡因浓度下进行光解反应的log k-pH分布图涉及多个步骤，表明直至pH 10的速率逐渐增加。在pH 2.0和10.5的速率较低是由于核黄素的电离，这从荧光测量中可以看出。核黄素与咖啡因相互作用的k'-pH曲线在3-6的pH范围内呈钟形曲线，在7-10的pH范围内呈S型曲线。咖啡因存在下抑