1-acetoxymethylthymine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-acetoxymethylthymine
• 英文别名: (5-Methyl-2,4-dioxopyrimidin-1-yl)methyl acetate；(5-methyl-2,4-dioxopyrimidin-1-yl)methyl acetate
• 化学式: C₈H₁₀N₂O₄
• 分子量: 198.178
• InChiKey: LGVPGGJEEYFNCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.63
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-acetoxymethylthymine 在 盐酸 作用下， 以75%的产率得到胸腺嘧啶
  参考文献：
  名称：

  Anodic decarboxylative oxidation of carboxymethyluracil and -thymine isomers

  摘要：

  The anodic oxidative decarboxylation of isomers of uracil and thymine acetic acids was studied. Electrolysis in methanolic or ethanolic solutions yielded respective alkoxymethyl derivatives via carbocationic intermediates. In acetic acid/sodium acetate medium, these were trapped by acetate, resulting in corresponding acetoxymethyl derivatives. Electrolysis in fully deuterated methanol or deuterated acetic acid, allow to obtain respective trideuterated compounds. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01151-9
• 作为产物：
  描述：

  胸腺嘧啶-1-乙酸 、 sodium acetate 、 溶剂黄146 以52%的产率得到1-acetoxymethylthymine
  参考文献：
  名称：

  Anodic decarboxylative oxidation of carboxymethyluracil and -thymine isomers

  摘要：

  The anodic oxidative decarboxylation of isomers of uracil and thymine acetic acids was studied. Electrolysis in methanolic or ethanolic solutions yielded respective alkoxymethyl derivatives via carbocationic intermediates. In acetic acid/sodium acetate medium, these were trapped by acetate, resulting in corresponding acetoxymethyl derivatives. Electrolysis in fully deuterated methanol or deuterated acetic acid, allow to obtain respective trideuterated compounds. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01151-9

文献信息

• Unexpected Reaction Products of Uracil and Its Methyl Derivatives with Acetic Anhydride and Methylene Chloride
  作者：Olga Michalak、Piotr Cmoch、Andrzej Leś、Marcin Cybulski、Piotr Krzeczyński、Kinga Trzcińska、Przemysław Miszta、Pakhuri Mehta、Sławomir Filipek

  DOI：10.1021/acs.joc.1c00748

  日期：2021.11.5

  that for products with the acetyloxyethyl group. In particular, for uracil it was proven that the reaction with Ac2O, TEA, and CH2Cl2 leads to 1-acetyloxymethyluracil, where the N1 substituent is composed of the −CH2– fragment that originated from CH2Cl2 and the 1-acetyloxy moiety from Ac2O. The reaction of uracil with Ac2O, TEA, CH2Cl2, and DMAP leads to an acetyloxyethyl derivative in which the −CH2–CH2–

  在二氯甲烷中非常规合成过程中获得了尿嘧啶、6-甲基尿嘧啶和胸腺嘧啶的新乙酰衍生物。结果表明，具有乙酰氧基甲基片段的产物是根据与具有乙酰氧基乙基的产物不同的机理形成的。特别是，对于尿嘧啶，已证明与 Ac 2 O、TEA 和 CH 2 Cl 2的反应产生 1-乙酰氧基甲基尿嘧啶，其中N 1取代基由源自 CH 2 Cl 2的 -CH 2 - 片段组成和来自 Ac 2 O的 1-乙酰氧基部分。尿嘧啶与 Ac 2 O、TEA、CH的反应2 Cl 2和 DMAP 产生乙酰氧基乙基衍生物，其中 -CH 2 -CH 2 - 片段来自 TEA，1-乙酰氧基部分来自 Ac 2 O。提出并支持形成新化合物的可能机制密度泛函理论/B3LYP 量子力学计算。新化合物（总共 39 种，包括 7 种氘代化合物）通过核磁共振和高分辨率质谱技术进行了全面表征。
• [EN] MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS OLIGOMÈRES MODIFIÉS ET LEURS UTILISATIONS
  申请人：IONIS PHARMACEUTICALS INC

  公开号：WO2021202788A2

  公开（公告）日：2021-10-07

  The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard 4' -thio nucleoside.