4-ethoxy-pyridine-2,6-dicarboxylic acid dimethyl ester | 63079-94-7

• 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: 4-ethoxy-pyridine-2,6-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 4-ethoxypyridine-2,6-dicarboxylate；dimethyl 4-ethoxypyridine-2,6-dicarboxylate
• CAS: 63079-94-7
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: MOAYXPXLNHNZEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-ethoxy-pyridine-2,6-dicarboxylic acid dimethyl ester 在 sodium tetrahydroborate 、 selenium(IV) oxide 、 magnesium chloride 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 反应 26.0h， 生成 (2E,12E)-16-Ethoxy-6,9-dioxa-3,12,18-triaza-bicyclo[12.3.1]octadeca-1(17),2,12,14(18),15-pentaene
  参考文献：
  名称：

  用于多元醇选择性酰化的凹形吡啶

  摘要：

  已经发现使用（双）大环吡啶 2 和 9 作为催化剂可以提高多元醇（1,2- 或 1,3- 烷二醇，部分保护的糖苷）的碱催化酰化的选择性。正如许多 X 射线分析（1a、1b、2a、2b、2e、9）所表明的那样，对于不同环尺寸（1 对 2）的凹形吡啶获得的不同选择性可能是由它们不同的几何形状引起的。甲基葡糖苷 7 可以选择性地在 2 位被酰化。

  DOI：

  10.1002/(sici)1099-0690(199806)1998:6<1077::aid-ejoc1077>3.0.co;2-6
• 作为产物：
  描述：

  4-氧代-1,4-二氢-2,6-吡啶二甲酸 在 氯化亚砜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成 4-ethoxy-pyridine-2,6-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Structure–activity relationship study of BACE1 inhibitors possessing a chelidonic or 2,6-pyridinedicarboxylic scaffold at the P2 position

  摘要：

  We have previously reported potent substrate-based pentapeptidic BACE1 inhibitors possessing a hydroxymethylcarbonyl isostere as a substrate transition-state mimic. While these inhibitors exhibited potent activities in enzymatic and cellular assays (KMI-429 in particular inhibited A beta production in vivo), these inhibitors contained some natural amino acids that seemed to be required to improve enzymatic stability in vivo and permeability across the blood-brain barrier, so as to be practical drug. Recently, we synthesized non-peptidic and small-sized BACE1 inhibitors possessing a heterocyclic scaffold at the P-2 position. Herein we report the SAR study of BACE1 inhibitors possessing this heterocyclic scaffold, a chelidonic or 2,6-pyridinedicarboxylic moiety. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.007

文献信息

• Structure–activity relationship study of BACE1 inhibitors possessing a chelidonic or 2,6-pyridinedicarboxylic scaffold at the P2 position
  作者：Yoshio Hamada、Kenji Suzuki、Tomoya Nakanishi、Diganta Sarma、Hiroko Ohta、Ryoji Yamaguchi、Moe Yamasaki、Koushi Hidaka、Shoichi Ishiura、Yoshiaki Kiso

  DOI：10.1016/j.bmcl.2013.12.007

  日期：2014.1

  We have previously reported potent substrate-based pentapeptidic BACE1 inhibitors possessing a hydroxymethylcarbonyl isostere as a substrate transition-state mimic. While these inhibitors exhibited potent activities in enzymatic and cellular assays (KMI-429 in particular inhibited A beta production in vivo), these inhibitors contained some natural amino acids that seemed to be required to improve enzymatic stability in vivo and permeability across the blood-brain barrier, so as to be practical drug. Recently, we synthesized non-peptidic and small-sized BACE1 inhibitors possessing a heterocyclic scaffold at the P-2 position. Herein we report the SAR study of BACE1 inhibitors possessing this heterocyclic scaffold, a chelidonic or 2,6-pyridinedicarboxylic moiety. (C) 2013 Elsevier Ltd. All rights reserved.
• Concave Pyridines for Selective Acylations of Polyols
  作者：Ulrich Lüning、Sönke Petersen、Wolfgang Schyja、Wolfgang Hacker、Torsten Marquardt、Kerstin Wagner、Michael Bolte

  DOI：10.1002/(sici)1099-0690(199806)1998:6<1077::aid-ejoc1077>3.0.co;2-6

  日期：1998.6

  Selectivity enhancements in the base-catalyzed acylation of polyols (1,2- or 1,3-alkanediol, partially protected glucoside) have been found with (bi)macrocyclic pyridines 2 and 9 as catalysts. The different selectivities obtained for concave pyridines of varying ring sizes (1 vs. 2) are probably caused by their different geometries as a number of X-ray analyses (1a, 1b, 2a, 2b, 2e, 9) indicate. The methyl

  已经发现使用（双）大环吡啶 2 和 9 作为催化剂可以提高多元醇（1,2- 或 1,3- 烷二醇，部分保护的糖苷）的碱催化酰化的选择性。正如许多 X 射线分析（1a、1b、2a、2b、2e、9）所表明的那样，对于不同环尺寸（1 对 2）的凹形吡啶获得的不同选择性可能是由它们不同的几何形状引起的。甲基葡糖苷 7 可以选择性地在 2 位被酰化。