(S)-3-methyl-10-(1'-hydroxy-3'-methylbutan-2'-yl)isoalloxazine | 93524-77-7

• 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
• 英文名称: (S)-3-methyl-10-(1'-hydroxy-3'-methylbutan-2'-yl)isoalloxazine
• 英文别名: 10-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-3-methylbenzo[g]pteridin-2,4-dione；10-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-3-methylbenzo[g]pteridine-2,4(3H,10H)-dione；10-[(2S)-1-hydroxy-3-methylbutan-2-yl]-3-methylbenzo[g]pteridine-2,4-dione
• CAS: 93524-77-7
• 化学式: C₁₆H₁₈N₄O₃
• 分子量: 314.344
• InChiKey: SAXXFHDMJAVPKU-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-methyl-10-(1'-hydroxy-3'-methylbutan-2'-yl)isoalloxazine 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到(1S)-(5H)-1,2-dihydro-5-methyl-1-(1-methylethyl)-4,6-dioxobenzo[g]imidazo-[1,2,3-ij]pteridin-12-ium chloride
  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
• 作为产物：
  描述：

  (S)-3-methyl 2-(2-nitrophenylamino)butan-1-ol 在 palladium on activated charcoal 氢气 作用下， 生成 (S)-3-methyl-10-(1'-hydroxy-3'-methylbutan-2'-yl)isoalloxazine
  参考文献：
  名称：

  NADH模型化合物与黄素之间的不对称辅酶氢转移

  摘要：

  手性黄素[（S）-3-甲基-10-（1'-羟基-3'-甲基丁烷-2'-基）异四恶嗪，（1b）]已合成：氢转移至（1b）和四（O来自手性NADH模型化合物的-乙酰基）核黄素仅在高浓度的Mg（ClO 4）2存在下才以不对称的方式发生。

  DOI：

  10.1039/c39840000849

文献信息

• N1,N10-Ethylene-bridged flavinium salts derived from l-valinol: synthesis and catalytic activity in H2O2 oxidations
  作者：Jiří Žurek、Radek Cibulka、Hana Dvořáková、Jiří Svoboda

  DOI：10.1016/j.tetlet.2009.12.096

  日期：2010.2

  Three chiral N1,N10-ethylene-bridged flavinium salts with a stereogenic centre derived from l-valinol are prepared and investigated as oxidation catalysts. These salts efficiently catalyse chemoselective H2O2 oxidation of sulfides to sulfoxides and the oxidation of 3-phenylcyclobutanone to the corresponding lactone at room temperature. The flavinium salts react with hydrogen peroxide to form flavin-10a-hydroperoxide

  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。
• Asymmetric intercoenzyme hydrogen transfer between NADH model compounds and flavins
  作者：Selji Shinkai、Hideki Nakao、Takaharu Tsuno、Osamu Manabe、Atsuyoshi Ohno

  DOI：10.1039/c39840000849

  日期：——

  A chiral flavin [(S)-3-methyl-10-(1′-hydroxy-3′-methylbutane-2′-yl)isoalloxazine, (1b)] has been synthesised: hydrogen transfer to (1b) and tetra(O-acetyl)riboflavin from chiral NADH model compounds occurred in an asymmetric manner only in the presence of high concentrations of Mg(ClO4)2.

  手性黄素[（S）-3-甲基-10-（1'-羟基-3'-甲基丁烷-2'-基）异四恶嗪，（1b）]已合成：氢转移至（1b）和四（O来自手性NADH模型化合物的-乙酰基）核黄素仅在高浓度的Mg（ClO 4）2存在下才以不对称的方式发生。
• Chiral ethylene-bridged flavinium salts: the stereoselectivity of flavin-10a-hydroperoxide formation and the effect of substitution on the photochemical properties
  作者：Jiří Žurek、Eva Svobodová、Jiří Šturala、Hana Dvořáková、Jiří Svoboda、Radek Cibulka

  DOI：10.1016/j.tetasy.2017.10.029

  日期：2017.12

  A series of chiral non-racemic N-1,N-10-ethylene bridged flavinium salts 4 was prepared using enantiomerically pure 2-substituted 2-aminoethanols (R = isopropyl, phenyl, benzyl, 4-methoxybenzyl, 4-benzyloxybenzyl) derived from amino acids as the sole source of chirality. The flavinium salts were shown to form 10a-hydroperoxy- and 10a-methoxy-adducts with moderate to high diastereoselectivity depending on the ethylene bridge substituent originating from the starting amino acid. High diastereoselectivities (dr values from 80:20 to >95:5) were observed for flavinium salts bearing benzyl substituents attached to the ethylene bridge. The benzyl group preferred the face-to-face (syn) orientation relative to the flavinium unit; thereby effectively preventing nucleophilic attack from one side. This conformation was found to be the most stable according to the DFT calculations. Consequently, the presence of benzyl groups causes intermolecular fluorescence quenching resulting in a significant decrease in the fluorescence quantum yield from 11% for 4a bearing an isopropyl substituent to 0.3% for 4c containing a benzyl group and to a value lower than 0.1% for the benzyloxybenzyl derivative 4e. (C) 2017 Elsevier Ltd. All rights reserved.