2,2',4',6-Tetramethoxy-4,5'-bipyrimidin | 56686-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2',4',6-Tetramethoxy-4,5'-bipyrimidin
• 英文别名: 4,5'-Bipyrimidine, 2,2',4',6-tetramethoxy-；4-(2,4-dimethoxypyrimidin-5-yl)-2,6-dimethoxypyrimidine
• CAS: 56686-17-0
• 化学式: C₁₂H₁₄N₄O₄
• 分子量: 278.268
• InChiKey: YUKGMTKTXANWIK-UHFFFAOYSA-N

物化性质

• 熔点：
  151-152 °C(Solv: hexane (110-54-3))
• 沸点：
  448.3±55.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2',4',6-Tetramethoxy-4,5'-bipyrimidin 在 氢溴酸 作用下， 以 水 为溶剂， 反应 23.0h， 生成 1'-methyl-4,5'-bipyrimidine-2,2'4',6(1H,1'H,3H,3'H)-tetrone
  参考文献：
  名称：

  Brown, Desmond J.; Strekowski, Lucjan, Australian Journal of Chemistry, 1981, vol. 34, # 5, p. 1157 - 1160

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴-2,4-二甲氧基嘧啶 生成 2,2',4',6-Tetramethoxy-4,5'-bipyrimidin
  参考文献：
  名称：

  MARUYAMA, TOKUMI;KIMURA, SHIHEI;HONJO, MIKIO, ORG. PREP. AND PROCED. INT., 20,(1988) N 5, C. 485-491

  摘要：

  DOI：

文献信息

• Deprotonative metalation of aromatic compounds using mixed lithium–iron combinations
  作者：Elisabeth Nagaradja、Floris Chevallier、Thierry Roisnel、Viatcheslav Jouikov、Florence Mongin

  DOI：10.1016/j.tet.2012.02.019

  日期：2012.4

  The deprotonation of 2-methoxypyridine was attempted using putative (TMP)(3)FeLi prepared from different iron sources. Using iodine to intercept the metalated 2-methoxypyridine, the best result was obtained from FeBr2 (1 equiv) using THF at room temperature: nevertheless, in addition to the expected iodide, the corresponding 2,2'-dimer was obtained (86% total yield). The origin of the competitive formation of the 2,2'-dimer was not identified but mechanisms were suggested to explain its formation. It was observed that the nature of the electrophile employed to trap the 3-metalated 2-methoxypyridine has a strong impact on this dimer formation, the latter being favored using iodine (35% yield), but also benzophenone (28%), benzoyl chloride (22%), methyl iodide (27%), allyl bromide (15%), benzyl bromide (41%), and tetramethylthiuram disulphide (36%); for this reason, the yields of the expected derivatives were only 51, 15, 62, 0, <5, 18, and 0%, respectively. In contrast, using aldehydes readily led to the expected pyridine alcohols without dimerization (59% yield using 3,4,5-trimethoxybenzaldehyde and 66% yield using pivalaldehyde). 2,6-Dimethoxypyridine (in 68% yield), anisole (47%), 2,4-dimethoxypyrimidine (50% at C5 and 3% at C6), 2-fluoropyridine (64%), and thiophene (49%) were similarly converted into the corresponding alcohols after subsequent trapping with pivalaldehyde. Using iodine to trap the 2-metalated anisole did not lead to dimer formation, and 2-iodoanisole was isolated in 71% yield. (C) 2012 Elsevier Ltd. All rights reserved.
• BROWN, D. J.;STREKOWSKI, L., AUSTRAL. J. CHEM., 1981, 34, N 5, 1157-1160
  作者：BROWN, D. J.、STREKOWSKI, L.

  DOI：——

  日期：——
• STREKOWSKI L., ROCZ. CHEM. <ROCH-AC>, 1974, 48, NO 12, 2157-2167
  作者：STREKOWSKI L.

  DOI：——

  日期：——
• MARUYAMA, TOKUMI;KIMURA, SHIHEI;HONJO, MIKIO, ORG. PREP. AND PROCED. INT., 20,(1988) N 5, C. 485-491
  作者：MARUYAMA, TOKUMI、KIMURA, SHIHEI、HONJO, MIKIO

  DOI：——

  日期：——
• Brown, Desmond J.; Strekowski, Lucjan, Australian Journal of Chemistry, 1981, vol. 34, # 5, p. 1157 - 1160
  作者：Brown, Desmond J.、Strekowski, Lucjan

  DOI：——

  日期：——