5-ethyl-1,3-dimethyl-5,10-dihydroalloxazine | 213384-71-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-ethyl-1,3-dimethyl-5,10-dihydroalloxazine
• 英文别名: 5-ethyl-1,3-dimethyl-10H-benzo[g]pteridine-2,4-dione
• CAS: 213384-71-5
• 化学式: C₁₄H₁₆N₄O₂
• 分子量: 272.307
• InChiKey: PYROZUTUPRJWSO-UHFFFAOYSA-N

物化性质

• 沸点：
  365.1±52.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 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：
  55.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-ethyl-1,3-dimethyl-5,10-dihydroalloxazine 在 air 作用下， 以85%的产率得到1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine
  参考文献：
  名称：

  Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts

  摘要：

  Flavin catalysts perform the first organocatalytic Dakin oxidation of electron-rich arylaldehydes to phenols under mild, basic conditions. Catechols are readily prepared, and the oxidation of 2-hydroxyacetophenone was achieved. Aerobic oxidation is displayed in the presence of Zn(0) as a reducing agent. This reactivity broadens the scope of biomimetic flavin catalysis in the realm of nucleophilic oxidations, providing a framework for mechanistic investigations for related oxidations, such as the Baeyer-Villiger oxidation and Weitz-Scheffer epoxidation.

  DOI：

  10.1021/ol3010326
• 作为产物：
  描述：

  1,3-dimethylalloxazine 、 乙醛 在 盐酸 、 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 5-ethyl-1,3-dimethyl-5,10-dihydroalloxazine
  参考文献：
  名称：

  易于用作和可重复使用的氧化催化剂的Alloxazinium-Resins

  摘要：

  Ñ 5改性alloxazinium盐，包括alloxazinium盐容易地制备5-乙基-1,3- dimethylalloxazinium和5-乙基-1,3-二甲基-8-（三氟甲基）alloxazinium树脂从相应Ñ经由5未改性的成分我们评估了先前由我们引入的用于制备异恶嗪类似物的好氧氧化-离子交换方案，以及它们在H 2 O 2氧化中的催化作用和可重复使用性。

  DOI：

  10.1246/bcsj.20210096
• 作为试剂：
  描述：

  三乙胺 在 双氧水 、 5-ethyl-1,3-dimethyl-5,10-dihydroalloxazine 作用下， 以 氘代甲醇 、 水 为溶剂， 生成 N,N-二乙基乙胺氧化物
  参考文献：
  名称：

  衍生自L-缬氨醇的N 1，N 10-乙烯桥接的黄酮盐：H 2 O 2氧化中的合成和催化活性

  摘要：

  制备了具有衍生自1-缬氨醇的立体异构中心的三种手性N 1，N 10-亚乙基桥黄酮盐，并将其作为氧化催化剂进行了研究。这些盐在室温下有效催化硫化物的化学选择性H 2 O 2氧化为亚砜和3-苯基环丁酮氧化为相应的内酯。所述flavinium盐与过氧化氢反应以形成黄素-10一氢过氧化物，它是负责对底物氧化的试剂。

  DOI：

  10.1016/j.tetlet.2009.12.096

文献信息

• Pyrazinium Salts as Efficient Organocatalysts of Mild Oxidations with Hydrogen Peroxide
  作者：Petra Ménová、František Kafka、Hana Dvořáková、Smita Gunnoo、Miloslav Šanda、Radek Cibulka

  DOI：10.1002/adsc.201000906

  日期：2011.4.18

  analogues of flavinium salts which are efficient organocatalysts for oxidations with hydrogen peroxide. It was shown that pyrazinium derivatives with an electron‐withdrawing substituent catalyze mild oxidations of sulfides to sulfoxides and Baeyer–Villiger oxidations in a similar way to flavinium catalysts. The most reactive catalyst, 3‐cyanopyrazinium tetrafluoroborate, was efficiently employed in preparative

  制备了一系列3-取代的吡嗪鎓四氟硼酸盐，作为黄酮盐的简单类似物，它们是用过氧化氢氧化的有效有机催化剂。结果表明，具有吸电子取代基的吡嗪鎓衍生物以与黄烷类催化剂相似的方式催化硫化物轻度氧化为亚砜和Baeyer-Villiger氧化。最具反应性的催化剂3-氰基吡嗪鎓四氟硼酸盐可有效地用于芳族和脂族硫化物的制备性硫氧化，以及环丁烷的拜尔-维利格（Baeyer-Villiger）氧化。所提出的催化机理是基于吡嗪氢过氧化物的形成，其是使底物氧化的试剂。
• Mild and Efficient Flavin-Catalyzed H₂O₂ Oxidation of Tertiary Amines to Amine <i>N</i>-Oxides
  作者：Katarina Bergstad、Jan-E. Bäckvall

  DOI：10.1021/jo980926d

  日期：1998.9.1

  A mild and highly effective H2O2 oxidation of tertiary amines has been developed by the use of flavin catalysis. Eight aliphatic amines were oxidized to their corresponding N-oxides in fast and selective reactions. For all substrates a considerable rate enhancement was observed compared to the noncatalyzed reactions. The product N-oxides were isolated in good yields using this mild oxidation system based on the environmentally attractive oxidant H2O2. As the catalyst, an N-1,N-5-dialkylated flavin was used as an analogue of the biologically important flavin redox cofactor. The catalytic cycle proposed for the flavin catalysis accounts for the observation that, in addition to the hydrogen peroxide oxidant, molecular oxygen is required for the initiation of the process.
• Alloxazinium-Resins as Readily Available and Reusable Oxidation Catalysts
  作者：Yukihiro Arakawa、Takayuki Kawahara、Keiji Minagawa、Yasushi Imada

  DOI：10.1246/bcsj.20210096

  日期：——

  N5-Modified alloxazinium salts including 5-ethyl-1,3-dimethylalloxazinium and 5-ethyl-1,3-dimethyl-8-(trifluoromethyl)alloxazinium salts were readily prepared as alloxazinium-resins from the corresponding N5-unmodified ingredients via the aerobic oxidation—ion exchange protocol, previously introduced by us for the preparation of isoalloxazine analogues, and their catalysis and reusability in H2O2 oxidations

  Ñ 5改性alloxazinium盐，包括alloxazinium盐容易地制备5-乙基-1,3- dimethylalloxazinium和5-乙基-1,3-二甲基-8-（三氟甲基）alloxazinium树脂从相应Ñ经由5未改性的成分我们评估了先前由我们引入的用于制备异恶嗪类似物的好氧氧化-离子交换方案，以及它们在H 2 O 2氧化中的催化作用和可重复使用性。
• Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts
  作者：Shuai Chen、Mohammad S. Hossain、Frank W. Foss

  DOI：10.1021/ol3010326

  日期：2012.6.1

  Flavin catalysts perform the first organocatalytic Dakin oxidation of electron-rich arylaldehydes to phenols under mild, basic conditions. Catechols are readily prepared, and the oxidation of 2-hydroxyacetophenone was achieved. Aerobic oxidation is displayed in the presence of Zn(0) as a reducing agent. This reactivity broadens the scope of biomimetic flavin catalysis in the realm of nucleophilic oxidations, providing a framework for mechanistic investigations for related oxidations, such as the Baeyer-Villiger oxidation and Weitz-Scheffer epoxidation.