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N-甲基胞嘧啶

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N-甲基胞嘧啶
IUPAC名
4-amino-1-methyl-2(1H)-pyrimidinone
识别
CAS号 1122-47-0  checkY
PubChem 79143
ChemSpider 71474
SMILES
 
  • CN1C=CC(=NC1=O)N
InChI
 
  • 1S/C5H7N3O/c1-8-3-2-4(6)7-5(8)9/h2-3H,1H3,(H2,6,7,9)
InChIKey HWPZZUQOWRWFDB-UHFFFAOYSA-N
ChEBI 39624
MeSH 1-Methylcytosine
性质
化学式 C5H7N3O
摩尔质量 125.13 g·mol−1
密度 1.4483 g·cm−3[1]
熔点 278—279 °C(551—552 K)[2]
沸点 300—303 °C(573—576 K)(分解)[3]
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

N-甲基胞嘧啶1-甲基胞嘧啶(简写:dS)是DNA碱基胞嘧啶C)的甲基化产物。N-甲基胞嘧啶可由胞嘧啶碘甲烷在一定条件下反应得到[4]硫酸二甲酯[5]三甲基氢氧化锍[6]也能作为甲基化试剂。

参考文献

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  1. ^ M. Rossi, T. J. Kistenmacher. 1-Methylcytosine: a refinement. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 1977-12-01, 33 (12): 3962–3965 [2019-03-18]. ISSN 0567-7408. doi:10.1107/S0567740877012618. (原始内容存档于2018-06-02). 
  2. ^ Johnson, T. B.; Clapp, S. H. Researches on Pyrimidines XXXIII: Syntheses of Some N Alkyl Derivatives of Cytosine, Thymine and Uracil. Journal of Biological Chemistry, 1909. 5: 49-70. ISSN: 0021-9258.
  3. ^ Ramachandra S. Hosmane, Nelson J. Leonard. Simple Convenient Synthesis of 1-Methylcytosine. Synthesis. 1981, 1981 (02): 118–119 [2019-03-18]. ISSN 0039-7881. doi:10.1055/s-1981-29352. (原始内容存档于2018-06-04) (英语). 
  4. ^ Steffi Noll, Marijeta Kralj, Lidija Šuman, Holger Stephan, Ivo Piantanida. Synthesis of modified pyrimidine bases and positive impact of chemically reactive substituents on their in vitro antiproliferative activity. European Journal of Medicinal Chemistry. 2009-3, 44 (3): 1172–1179 [2019-03-18]. doi:10.1016/j.ejmech.2008.06.002. (原始内容存档于2018-06-29) (英语). 
  5. ^ Bredereck, Hellmut; Haas, Hans; Martini, Annelise. Nucleic acids. XXIII. Methylated nucleosides and purines and their pharmacological effects. 2. Methylation of nucleosides with dimethyl sulfate. Chemische Berichte, 1948. 81: 307-313. ISSN: 0009-2940.
  6. ^ Kiyoshi Yamauchi, Toshizumi Tanabe, Masayoshi Kinoshita. Trimethylsulfonium hydroxide: a new methylating agent. The Journal of Organic Chemistry. 1979-2, 44 (4): 638–639 [2019-03-18]. ISSN 0022-3263. doi:10.1021/jo01318a037. (原始内容存档于2019-10-18) (英语).