N-(1,4-二氢-6-甲基-5-硝基-4-氧代-嘧啶-2-基)-乙酰胺 | 299916-90-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(1,4-二氢-6-甲基-5-硝基-4-氧代-嘧啶-2-基)-乙酰胺
• 中文别名: 2H-吡喃-2-酮,3-(二氟乙酰基)四氢-,(+)-(9CI)；N-(4-羟基-6-甲基-5-硝基嘧啶-2-基)醋胺石
• 英文名称: 2-N-acetylamino-6-methyl-5-nitropyrimidin-4-one
• 英文别名: 2-acetamide-5-nitro-6-methylpyrimidin-4-one；2-acetamido-5-nitro-6-methylpyrimidin-4-one；N-(4-methyl-5-nitro-6-oxo-1,6-dihydro-pyrimidin-2-yl)-acetamide；N-(4-Methyl-5-nitro-6-oxo-1,6-dihydro-pyrimidin-2-yl)-acetamid；N-(4-hydroxy-6-methyl-5-nitropyrimidin-2-yl)acetamide；N-(4-methyl-5-nitro-6-oxo-1H-pyrimidin-2-yl)acetamide
• CAS: 299916-90-8
• 化学式: C₇H₈N₄O₄
• 分子量: 212.165
• InChiKey: FTUUKELCLGAATN-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C (decomp)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(1,4-二氢-6-甲基-5-硝基-4-氧代-嘧啶-2-基)-乙酰胺 在 palladium on activated charcoal 作用下， 生成 N-(5-amino-4-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-acetamide
  参考文献：
  名称：

  Sirakawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 643

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(6-甲基-4-氧代-1H-嘧啶-2-基)乙酰胺 在 硫酸 、 硝酸 作用下， 生成 N-(1,4-二氢-6-甲基-5-硝基-4-氧代-嘧啶-2-基)-乙酰胺
  参考文献：
  名称：

  Sirakawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 643

  摘要：

  DOI：

文献信息

• Addition of Lithiated 9-Deazapurine Derivatives to a Carbohydrate Cyclic Imine:  Convergent Synthesis of the Aza-<i>C</i>-nucleoside Immucillins
  作者：Gary B. Evans、Richard H. Furneaux、Tracy L. Hutchison、Hollis S. Kezar、Philip E. Morris,、Vern L. Schramm、Peter C. Tyler

  DOI：10.1021/jo0155613

  日期：2001.8.1

  Means have been developed for the synthesis and addition of 9-deaza-9-lithiopurine derivatives to the carbohydrate-derived cyclic imine 6 in facile convergent syntheses of biologically active aza-C-nucleosides.

  已经开发了在生物活性氮杂-C-核苷的容易会聚合成中将9-脱氮基-9-硫代嘌呤衍生物合成和添加至碳水化合物衍生的环亚胺6的方法。
• Process for preparing 2-pyrrolidinyl-1H-pyrrolo&lsqb;3,2-d&rsqb;pyrimidine inhibitors of nucleoside metabolism
  申请人：Industrial Research Limited

  公开号：US06693193B1

  公开（公告）日：2004-02-17

  A process of preparing a compound of the formula (I) wherein B is chosen from OH, NH2, NHR, H or halogen; D is chosen from OH, NH2, NHR, H halogen or SCH3; R is an optionally substituted alkyl, aralkyl or aryl group; and Z is selected from OH, hydrogen, halogen, hydroxy, SQ or OQ, Q is an optionally substituted all, aralkyl or aryl group; or a tautomer thereof; or a pharmaceutically acceptable salt thereof; or an ester thereof; or a prodrug thereof, which comprises reacting a compound of the formula (II)  with an anion produced by abstraction of the bromine or iodine atom from a compound of formula (XIX),  to form a compound of formula (XX) The compound of formula (XX) is N- and O-deprotected to obtain the compound of formula (I).

  将公式（I）的化合物制备过程翻译成中文： 其中B选择自OH、NH2、NHR、H或卤素；D选择自OH、NH2、NHR、H、卤素或SCH3；R是可选择取代的烷基、芳基烷基或芳基；Z选择自OH、氢、卤素、羟基、SQ或OQ，Q是可选择取代的烷基、芳基烷基或芳基；或其互变异构体；或其药学上可接受的盐；或其酯；或其前药，包括将公式（II）的化合物与通过从公式（XIX）的化合物中提取溴或碘原子而产生的负离子反应，形成公式（XX）的化合物。公式（XX）的化合物经N-和O去保护得到公式（I）的化合物。
• Process for preparing inhibitors of nucleoside metabolism
  申请人：Furneaux Hubert Richard

  公开号：US20070161667A1

  公开（公告）日：2007-07-12

  A process of preparing a compound of the formula (I) wherein B is chosen from OH, NH 2 , NHR, H or halogen; D is chosen from OH, NH 2 , NHR, H halogen or SCH 3 ; R is an optionally substituted alkyl, aralkyl or aryl group; and Z is selected from OH, hydrogen, halogen, hydroxy, SQ or OQ, Q is an optionally substituted alkyl, aralkyl or aryl group; or a tautomer thereof; or a pharmaceutically acceptable salt thereof; or an ester thereof; or a prodrug thereof, which comprises reacting a compound of the formula (II) with an anion produced by abstraction of the bromine or iodine atom from a compound of formula (XIX),

  制备公式（I）化合物的过程，其中B选自OH，NH2，NHR，H或卤素；D选自OH，NH2，NHR，H，卤素或SCH3；R是可选取的取代基的烷基，芳基烷基或芳基；Z选自OH，氢，卤素，羟基，SQ或OQ，Q是可选取的取代基的烷基，芳基烷基或芳基；或其互变异构体；或其药学上可接受的盐；或其酯；或其前药。该过程包括将公式（II）化合物与从公式（XIX）化合物中提取溴或碘原子所产生的阴离子反应。
• Synthesis of 2-amino-4-hydroxyl-6-hydroxymethyl-5,6,7,8-tetrahydropyrido[3,2-<i>d</i>]pyrimidine from 2-amino-4-hydroxyl-6-methylpyrimidine
  作者：Zhili Zhang、Jie Liu、Weidong Liu、Xiaowei Wang、Zhijian Cheng、Junyi Liu

  DOI：10.1002/jhet.197

  日期：2009.11

  Abstract magnified image The synthesis of 2‐amino‐4‐hydroxyl‐6‐hydroxymethyl‐5,6,7,8‐tetrahydropyrido[3,2‐d]pyrimidine 3 is described from 2‐amino‐6‐methyluracil 4 through the crucial step of 2‐pivaloyl protecting and cyclization. The assignment of the structure of 3 was performed by its spectral data, the 1H NMR, 13C NMR, gHMQC, and HRMS spectra. J. Heterocyclic Chem., (2009).
• Synthesis of 1-Amino-6,7-dihydro-7-(hydroxymethyl)-4-nitro-pyrrolo[1,2-f]pyrimidin-3-(5H)-one from 2-Amino-6-methylpyrimidin-3-one
  作者：Jie Liu、Weidong Liu、Zhili Zhang、Zhijian Cheng、Xiaoyan Ma、Xiaowei Wang、Junyi Liu

  DOI：10.1080/00397910802654732

  日期：2009.5.22

  The synthesis of previously unreported 1-amino-6,7-dihydro-7-(hydroxymethyl)-4-nitropyrrolo[1,2-f]pyrimidin-3-(5H)-one starting from 2-amino-6-methylpyrimidin-3-one is described.