4-chloro-6-methyl-3-nitro-2H-pyran-2-one | 106353-76-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物
• 英文名称: 4-chloro-6-methyl-3-nitro-2H-pyran-2-one
• 英文别名: 4-chloro-3-mitro-2H-pyran-2-one；4-Chloro-6-methyl-3-nitropyran-2-one
• CAS: 106353-76-8
• 化学式: C₆H₄ClNO₄
• 分子量: 189.555
• InChiKey: ZUORAEQVLOEBEV-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C(Solv: ethyl acetate (141-78-6); cyclohexane (110-82-7))
• 沸点：
  232.6±40.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-6-methyl-3-nitro-2H-pyran-2-one 在 sodium azide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 4-[2-(nitromethyl)-6-(2-phenylethyl)pyridin-4-yl]morpholine
  参考文献：
  名称：

  Synthesis of 4-dialkylaminopyridine derivatives through ring-rearrangement of 3-nitro-2H-pyran-2-one acetamidines

  摘要：

  A new synthesis of substituted 4-dialkylaminopyridines was developed, starting from 3-nitropyran-2-one N-functionalized amidines. Secondary amines were reacted with the amidines in a sealed tube and in ethanol as the solvent yielding exclusively 4-dialkylaminopyridine derivatives or a mixture with 4-methylpyridine derivative, depending on the C-alpha-linked substituents of the starting amidine. Structural elucidation of the 4-dialkylaminopyridines revealed their existence as two tautomeric forms, depending on the solvent. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.022
• 作为产物：
  描述：

  4-羟基-6-甲基-3-硝基吡喃-2-酮 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到4-chloro-6-methyl-3-nitro-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis of 4-dialkylaminopyridine derivatives through ring-rearrangement of 3-nitro-2H-pyran-2-one acetamidines

  摘要：

  A new synthesis of substituted 4-dialkylaminopyridines was developed, starting from 3-nitropyran-2-one N-functionalized amidines. Secondary amines were reacted with the amidines in a sealed tube and in ethanol as the solvent yielding exclusively 4-dialkylaminopyridine derivatives or a mixture with 4-methylpyridine derivative, depending on the C-alpha-linked substituents of the starting amidine. Structural elucidation of the 4-dialkylaminopyridines revealed their existence as two tautomeric forms, depending on the solvent. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.022

文献信息

• Synthesis of 4-nitromethylene-1,4-dihydropyrimidine derivatives as pyrimidine nucleoside analogues
  作者：Alessandro Contini、Emanuela Erba、Pasqualina Trimarco

  DOI：10.1016/j.tet.2008.09.079

  日期：2008.12

  4-dihydropyrimidine derivatives as pyrimidine nucleoside analogues was developed, starting from 3-nitropyran-2-one N-functionalized amidines. Primary amines were reacted with amidines yielding 4-nitromethylene-1,4-dihydropyrimidine derivatives. In an initial survey, several 4-nitromethylene-1,4-dihydropyrimidines turned into 4-nitromethylene-1,2,3,4-tetrahydropyrimidine derivatives under different reduction

  从3-硝基吡喃-2-酮N-官能化am开始，开发了作为嘧啶核苷类似物的4-硝基亚甲基-1,4-二氢嘧啶衍生物。使伯胺与am反应，得到4-硝基亚甲基-1,4-二氢嘧啶衍生物。在初步调查中，几种4-硝基亚甲基-1,4-二氢嘧啶在不同的还原条件下转变为4-硝基亚甲基1,2,3,4-四氢嘧啶衍生物。由于分子内氢键，还原反应还引起环外双键构型从（E）变化为（Z）。
• Akhtar, Nahid; Munawar, M. A.; Siddiq, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 328
  作者：Akhtar, Nahid、Munawar, M. A.、Siddiq, M.

  DOI：——

  日期：——
• AKHTAR NAHID; MUNAWAR M. A.; SIDDIO M., INDIAN J. CHEM., 25,(1986) N 3, 328
  作者：AKHTAR NAHID、 MUNAWAR M. A.、 SIDDIO M.

  DOI：——

  日期：——