10-(3-Hydroxy-propyl)-7,8-dimethyl-5-oxy-10H-benzo[g]pteridine-2,4-dione | 1026052-72-1

• 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: 10-(3-Hydroxy-propyl)-7,8-dimethyl-5-oxy-10H-benzo[g]pteridine-2,4-dione
• 英文别名: 10-(3-Hydroxypropyl)-7,8-dimethyl-5-oxidobenzo[g]pteridin-5-ium-2,4-dione
• CAS: 1026052-72-1
• 化学式: C₁₅H₁₆N₄O₄
• 分子量: 316.316
• InChiKey: YBVVJESQDWDEFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-(3-Hydroxy-propyl)-7,8-dimethyl-5-oxy-10H-benzo[g]pteridine-2,4-dione 在 1,4-二巯基-2,3-丁二醇 作用下， 以 乙醇 为溶剂， 生成 10-(3-hydroxy-propyl)-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione
  参考文献：
  名称：

  Method for Preparing New Flavin Derivatives:  Synthesis of Flavin−Thymine Nucleotides and Flavin−Oligonucleotide Adducts

  摘要：

  In order to link to the 5'-end of oligonucleotides the flavin analogs 9a,b possessing only one terminal hydroxy group on the side chain, the phosphoramidite and the H-phosphonate coupling methods were developed. Surprisingly, after reaction of compounds 9a,b with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, the flavin phosphoramidates 11a,b were isolated instead of the expected phosphoramidite derivatives 10a,b. A very efficient photooxidation process occurred probably during the isolation of the products. From the prepared flavin H-phosphonates 12a,b, flavin-thymine nucleotides and flavin-oligonucleotide adducts were synthesized for the first time. The versatility of the method was demonstrated in the oxidation step with the synthesis of the flavin-thymine nucleotides 15-17 possessing a phosphodiester, a phosphorothioate, and a methyl phosphate linkage, respectively. This method is of general interest with regard to the extensive research developed for preparing flavin analogs and modified oligonucleotides possessing interesting biological or/and catalytic properties.

  DOI：

  10.1021/jo962361w
• 作为产物：
  描述：

  3-(3,4-dimethyl-phenylamino)-propan-1-ol 在 sodium nitrate 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 为溶剂， 生成 10-(3-Hydroxy-propyl)-7,8-dimethyl-5-oxy-10H-benzo[g]pteridine-2,4-dione
  参考文献：
  名称：

  Method for Preparing New Flavin Derivatives:  Synthesis of Flavin−Thymine Nucleotides and Flavin−Oligonucleotide Adducts

  摘要：

  In order to link to the 5'-end of oligonucleotides the flavin analogs 9a,b possessing only one terminal hydroxy group on the side chain, the phosphoramidite and the H-phosphonate coupling methods were developed. Surprisingly, after reaction of compounds 9a,b with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, the flavin phosphoramidates 11a,b were isolated instead of the expected phosphoramidite derivatives 10a,b. A very efficient photooxidation process occurred probably during the isolation of the products. From the prepared flavin H-phosphonates 12a,b, flavin-thymine nucleotides and flavin-oligonucleotide adducts were synthesized for the first time. The versatility of the method was demonstrated in the oxidation step with the synthesis of the flavin-thymine nucleotides 15-17 possessing a phosphodiester, a phosphorothioate, and a methyl phosphate linkage, respectively. This method is of general interest with regard to the extensive research developed for preparing flavin analogs and modified oligonucleotides possessing interesting biological or/and catalytic properties.

  DOI：

  10.1021/jo962361w

文献信息

• Method for Preparing New Flavin Derivatives:  Synthesis of Flavin−Thymine Nucleotides and Flavin−Oligonucleotide Adducts
  作者：Christelle Frier、Jean-Luc Décout、Marc Fontecave

  DOI：10.1021/jo962361w

  日期：1997.5.1

  In order to link to the 5'-end of oligonucleotides the flavin analogs 9a,b possessing only one terminal hydroxy group on the side chain, the phosphoramidite and the H-phosphonate coupling methods were developed. Surprisingly, after reaction of compounds 9a,b with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, the flavin phosphoramidates 11a,b were isolated instead of the expected phosphoramidite derivatives 10a,b. A very efficient photooxidation process occurred probably during the isolation of the products. From the prepared flavin H-phosphonates 12a,b, flavin-thymine nucleotides and flavin-oligonucleotide adducts were synthesized for the first time. The versatility of the method was demonstrated in the oxidation step with the synthesis of the flavin-thymine nucleotides 15-17 possessing a phosphodiester, a phosphorothioate, and a methyl phosphate linkage, respectively. This method is of general interest with regard to the extensive research developed for preparing flavin analogs and modified oligonucleotides possessing interesting biological or/and catalytic properties.