dimethyl 5-hydroxy-6-methyl-2,3-pyridinedicarboxylate | 130721-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: dimethyl 5-hydroxy-6-methyl-2,3-pyridinedicarboxylate
• 英文别名: dimethyl 5-hydroxy-6-methylpyridine-2,3-dicarboxylate；5-hydroxy-6-methyl-pyridine-2,3-dicarboxylic acid dimethyl ester；5-Hydroxy-6-methyl-pyridin-2,3-dicarbonsaeure-dimethylester；2,3-Dimethyl 5-hydroxy-6-methyl-2,3-pyridinedicarboxylate
• CAS: 130721-05-0
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: OMFWAYJPJWKDTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-cyano-6-methyl-pyridine-2,3-dicarboxylic acid diethyl ester 在 盐酸 、 alkaline NaClO 、 硫酸 、 sodium nitrite 作用下， 生成 dimethyl 5-hydroxy-6-methyl-2,3-pyridinedicarboxylate
  参考文献：
  名称：

  Pyridine Syntheses. IV. The Preparation of Some Vitamin B₆ Analogs

  摘要：

  DOI：

  10.1021/ja01126a040

文献信息

• Correlations between carbon-13 nuclear magnetic resonance chemical shifts and reactivities of siloxybutadienes and siloxyazabutadienes in the Diels-Alder reaction with dimethyl acetylenedicarboxylate.
  作者：Jun-etsu IGARASHI、Yoshinari KAWAKAMI、Toshio KINOSHITA、Sunao FURUKAWA

  DOI：10.1248/cpb.38.1832

  日期：——

  In the reaction of silylated butadiene derivatives (1) with dimethyl acetylenedicarboxylate (DMAD), it is proposed that the reactivities of the dienes can be predicted from the carbon-13 nuclear magnetic resonance chemical shifts of the terminal methylene carbons (δ13C-4) of the dienes based on the following linear relationships, a) total electron densities against δ13C-4; b) ln k against 1/[ELUMO(DMAD)-EHOMO(diene)]; c) ln k against δ13C-4. The total electron densities and energy levels of highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) of the dienes were calculated by the modified neglect of diatomic overlap (MNDO) method.

  在硅烷化丁二烯衍生物 (1) 与乙炔二甲酸二甲酯（DMAD）的反应中，建议根据二烯末端亚甲基碳（δ13C-4）的碳-13 核磁共振化学位移，按照以下线性关系预测二烯的反应活性：a) 总电子密度与δ13C-4 的关系；b) ln k 对 1/[ELUMO（DMAD）-EHOMO（二烯）]； c) ln k 对 δ13C-4。二烯的总电子密度以及最高占位分子轨道（HOMOs）和最低未占位分子轨道（LUMOs）的能级是通过修正的忽略二原子重叠（MNDO）法计算得出的。
• Synthesis of highly-functionalised pyridines via hetero-Diels–Alder methodology: reaction of 3-siloxy-1-aza-1,3-butadienes with electron deficient acetylenes
  作者：Matthew D. Fletcher、Timothy E. Hurst、Timothy J. Miles、Christopher J. Moody

  DOI：10.1016/j.tet.2006.03.051

  日期：2006.6

  The hetero-Diels-Alder reaction between 1-aza-3-siloxy-1,3-butadienes and electron deficient acetylenes is described. The reactivity of a range of alpha,beta-unsaturated oximes and hydrazones is assessed in the synthesis of tri- and tetra-substituted pyridines bearing an oxygen functionality at C-3. Microwave irradiation has been employed to decrease the extended reaction times and increase the poor yields often associated with this reaction. (c) 2006 Elsevier Ltd. All rights reserved.
• Pyridine Syntheses. IV. The Preparation of Some Vitamin B₆ Analogs
  作者：Reuben G. Jones

  DOI：10.1021/ja01126a040

  日期：1952.3