6-甲氧基-5-甲基-2(1H)-嘧啶酮 | 25902-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-甲氧基-5-甲基-2(1H)-嘧啶酮
• 英文名称: 4-methoxy-5-methyl-pyrimidin-2(1H)-one
• 英文别名: 4-methoxy-5-methyl-2(1H)-pyrimidinone；4-methoxy-5-methylpyrimidin-2(1H)-one；5-methyl-4-methoxypyrimidin-2(1H)-one；4-methoxy-5-methyl-2-pyrimidinone；5-Methyl-4-methoxy-2-pyrimidinone；4-Methoxy-5-methyl-2-pyrimidone；O-4-Methylthymine；6-methoxy-5-methyl-1H-pyrimidin-2-one
• CAS: 25902-89-0
• 化学式: C₆H₈N₂O₂
• mdl: MFCD10569824
• 分子量: 140.142
• InChiKey: NWUTZAVMDAGNIG-UHFFFAOYSA-N

物化性质

• 熔点：
  182-183 °C(Solv: methanol (67-56-1))
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  6-甲氧基-5-甲基-2(1H)-嘧啶酮 在 氨 作用下， 以 甲醇 为溶剂， 生成 5-甲基胞嘧啶
  参考文献：
  名称：

  Holy, Antonin; Rosenberg, Ivan; Dvorakova, Hana, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 8, p. 2190 - 2210

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯-2-乙硫基-5-甲基-嘧啶 在 甲醇 、 双氧水 作用下， 生成 6-甲氧基-5-甲基-2(1H)-嘧啶酮
  参考文献：
  名称：

  Chi; Chen, Scientia Sinica (English Edition), 1957, vol. 6, p. 477,484

  摘要：

  DOI：

文献信息

• Bifunctional Acyclic Nucleoside Phosphonates: 2. Symmetrical 2-{[Bis(phosphono)methoxy]methyl}ethyl Derivatives of Purines and Pyrimidines
  作者：Silvie Vrbková、Martin Dračínský、Antonín Holý

  DOI：10.1135/cccc20070965

  日期：——

  Novel bisphosphonate alkylating agent, tetraisopropyl 2-[(mesyloxy)methyl]propane-1,3-diyl}bis(oxymethylene)bisphosphonate 19, was synthesized from diethyl 2,2-bis(hydroxymethyl)malonate. Decarbethoxylation of the diethyl 2,2-dimethyl-1,3-dioxane-5,5-dicarboxylate was followed by chloromethylation of 2-[(benzyloxy)methyl]propane-1,3-diol and Arbuzov reaction with triisopropyl phosphite. Bisphosphonate building block 19 was used in the alkylation of various nucleobases (2-amino-6-chloropurine, adenine, 2-amino-6-(cyclopropyl)aminopurine, cytosine, uracil and 4-methoxy-5-methylpyrimidin-2(1H)-one). N⁹-Substituted purines and N¹-substituted pyrimidines were converted to appropriate free bisphosphonic acids. No antiviral or cytostatic activity was detected.

  新型双膦酸烷基化剂，四异丙基2-[(mesyloxy)methyl]丙烷-1,3-二基}双(氧甲基)双膦酸酯19，是由二乙酯2,2-双(羟甲基)丙二酸酯合成的。首先对二乙酯2,2-二甲基-1,3-二氧杂环戊二酸酯进行去羧乙酰化，然后对2-[(苄氧基)甲基]丙烷-1,3-二醇进行氯甲基化，再进行与三异丙基磷酸酯的阿布佐夫反应。双膦酸酯基团19被用于烷基化各种核碱基（2-氨基-6-氯嘌呤、腺嘌呤、2-氨基-6-(环丙基)氨基嘌呤、胞嘧啶、尿嘧啶和4-甲氧基-5-甲基嘧啶-2(1H)-酮）。N9-取代嘌呤和N1-取代嘧啶被转化为相应的自由双膦酸。未检测到抗病毒或细胞毒活性。
• beta-DIHYDROFURAN DERIVING COMPOUND, METHOD FOR PRODUCING beta-DIHYDROFURAN DERIVING COMPOUND OR beta-TETRAHYDROFURAN DERIVING COMPOUND, beta-GLYCOSIDE COMPOUND, METHOD FOR PRODUCING beta GLYCOSIDE COMPOUND, AND METHOD FOR PRODUCING 4'-ETHYNYL D4T AND ANALOGUE COMPOUNDS THEREOF
  申请人：Iriyama Yusuke

  公开号：US20120322995A1

  公开（公告）日：2012-12-20

  The invention provides a process for producing a β-dihydrofuran derivative represented by formula (1) or a β-tetrahydrofuran derivative represented by formula (4), characterized in that the process includes causing a dialkyl dicarbonate, a diaralkyl dicarbonate, or a halide to act on a diol compound represented by formula (2) or (3). The invention also provides a process for producing 4′-ethynyl-2′,3′-didehydro-3′-deoxythymidine or an analog thereof, the process including glycosylation and deprotection.

  该发明提供了一种生产由式（1）表示的β-二氢呋喃衍生物或由式（4）表示的β-四氢呋喃衍生物的过程，其特征在于该过程包括使二烷基二碳酸酯、二芳基二碳酸酯或卤化物作用于由式（2）或（3）表示的二醇化合物。该发明还提供了一种生产4'-乙炔基-2',3'-二去氢-3'-脱氧胸苷或其类似物的过程，包括糖基化和去保护。
• Acyclic Nucleoside Phosphonates Bearing (<i>R</i> )- or (<i>S</i> )-9-[3-Hydroxy-2-(phosphonoethoxy)propyl] (HPEP) Moiety as Monomers for the Synthesis of Modified Oligonucleotides
  作者：Martin Maxmilian Kaiser、Pavel Novák、Šárka Rosenbergová、Lenka Poštová-Slavětínská、Ivan Rosenberg、Zlatko Janeba

  DOI：10.1002/ejoc.201800490

  日期：2018.10.9

  A solid‐phase synthesis afforded a series of ribo and 2′‐deoxyribo nonamers containing acyclic nucleotide units. A general destabilizing effect of the introduced acyclic units on the thermal stability of complexes of modified nonamers with the complementary DNA and RNA strands was observed, but in cases with (S)‐HPEPA units, the duplexes were characterized in terms of Tm values.

  固相合成提供了一系列包含无环核苷酸单元的核糖和2'-脱氧核糖九聚体。观察到了引入的无环单元对修饰的九聚体与互补的DNA和RNA链复合物的热稳定性的一般去稳定作用，但是在具有（S）-HPEPA单元的情况下，双链体以T m值表征。
• Process for the preparation of 5-substituted cytosines and other
  申请人：Hoechst Aktiengesellschaft

  公开号：US05359067A1

  公开（公告）日：1994-10-25

  Process for the preparation of 5-substituted cytosines and other 4,5-disubstituted pyrimidin-2(1H)-ones, and intermediates arising in the course of this The process for the preparation of compounds of the formula I, ##STR1## wherein compounds of the formula II ##STR2## are converted into an azole derivative of the formula III or an azine derivative of the formula IV ##STR3## which can subsequently be converted into a compound of the formula I using a nucleophile XH.

  制备5-取代胞嘧啶和其他4,5-二取代嘧啶-2(1H)-酮的方法，以及在此过程中产生的中间体。制备式I的化合物的方法，其中式II的化合物被转化为式III的唑类衍生物或式IV的噁唑类衍生物，随后可以使用亲核试剂XH将其转化为式I的化合物。
• Synthesis of Optically Active N6-Alkyl Derivatives of (R)-3-(Adenin-9-yl)-2-hydroxypropanoic Acid and Related Compounds
  作者：Marcela Krečmerová、Miloš Buděšínský、Milena Masojídková、Antonín Holý

  DOI：10.1135/cccc20030931

  日期：——

  Reaction of ethyl (R)-oxiranecarboxylate (2a) with various nucleobases (adenine, 6-chloropurine, thymine, cytosine, N⁶-benzoyladenine, 4-methoxy-5-methylpyrimidin-2(1H)-one and 4-methoxypyrimidin-2(1H)-one) afforded ethyl 3-substituted-2-hydroxypropanoates 4-10. Enantioselectivity of this reaction is dependent on the type of the base: 6-chloropurine, N⁶-benzoyladenine, 4-methoxy-5-methylpyrimidin-2(1H)-one, thymine and cytosine gave optically pure R enantiomers. In other cases, partial or complete racemization occurred. Optically pure ethyl (R)-3-(6-chloropurin-9-yl)-2-hydroxypropanoate (5a) was hydrolyzed to give (R)-3-(6-chloropurin-9-yl)-2-hydroxypropanoic acid (11). Reactions of 11 with various primary or secondary amines led to N⁶-substituted (R)-3-(adenin-9-yl)-2-hydroxypropanoic acids 14-19. Enantiomeric purity was determined from ¹H NMR spectra measured in the presence of (-)-(R)-1-(9-anthryl)-2,2,2-trifluoroethan-1-ol.

  乙基（R）-环氧丙酸乙酯（2a）与各种核碱基（腺嘌呤、6-氯嘌呤、胸腺嘧啶、胞嘧啶、N6-苯甲酰腺嘌呤、4-甲氧基-5-甲基嘧啶-2（1H）-酮和4-甲氧基嘧啶-2（1H）-酮）反应生成乙基3-取代-2-羟基丙酸酯4-10。该反应的对映选择性取决于碱基的类型：6-氯嘌呤、N6-苯甲酰腺嘌呤、4-甲氧基-5-甲基嘧啶-2（1H）-酮、胸腺嘧啶和胞嘧啶生成光学纯R对映异构体。在其他情况下，部分或完全消旋发生。光学纯乙基（R）-3-（6-氯嘌呤-9-基）-2-羟基丙酸酯（5a）水解得到（R）-3-（6-氯嘌呤-9-基）-2-羟基丙酸（11）。11与各种一级或二级胺的反应导致N6-取代（R）-3-（腺嘌呤-9-基）-2-羟基丙酸14-19。对映纯度是通过在(-)-（R）-1-（9-蒽基）-2,2,2-三氟乙醇存在下测定的1H NMR谱来确定的。