2-(α-Hydroxy-3,4-dimethoxybenzyl)pyridine-3-carbaldehyde dimethyl acetal | 123694-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(α-Hydroxy-3,4-dimethoxybenzyl)pyridine-3-carbaldehyde dimethyl acetal
• 英文别名: [3-(Dimethoxymethyl)pyridin-2-yl]-(3,4-dimethoxyphenyl)methanol
• CAS: 123694-51-9
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: RIRGOHAOJBYVTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(α-Hydroxy-3,4-dimethoxybenzyl)pyridine-3-carbaldehyde dimethyl acetal 在 三氟乙酸 草酸 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 0.67h， 生成 5-Hydroxy-6,7-bis(methoxycarbonyl)-8-(3,4-dimethoxyphenyl)quinoline
  参考文献：
  名称：

  An Efficient Synthesis of Heterocyclic Analogs of 1-Arylnaphthalene Lignans

  摘要：

  The heterocyclic analogs 5a-f, 16, and 20 of 1-arylnaphthalene lignans were synthesized by Diels-Alder reactions of acetoxy aldehydes 11a-f, 14, and 18 with dimethyl acetylenedicarboxylate. A pathway for formation of 5a-f, 16, and 20 through the intermediacy of heteroaromatic isobenzofurans derived from acetoxy aldehydes is discussed.

  DOI：

  10.1021/jo00103a029
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 2-Bromopyridine-3-carbaldehyde dimethyl acetal 在 正丁基锂 作用下， 以83%的产率得到2-(α-Hydroxy-3,4-dimethoxybenzyl)pyridine-3-carbaldehyde dimethyl acetal
  参考文献：
  名称：

  An Efficient Synthesis of Heterocyclic Analogs of 1-Arylnaphthalene Lignans

  摘要：

  The heterocyclic analogs 5a-f, 16, and 20 of 1-arylnaphthalene lignans were synthesized by Diels-Alder reactions of acetoxy aldehydes 11a-f, 14, and 18 with dimethyl acetylenedicarboxylate. A pathway for formation of 5a-f, 16, and 20 through the intermediacy of heteroaromatic isobenzofurans derived from acetoxy aldehydes is discussed.

  DOI：

  10.1021/jo00103a029

文献信息

• An Efficient Synthesis of Heterocyclic Analogs of 1-Arylnaphthalene Lignans
  作者：Tooru Kuroda、Masami Takahashi、Tsuyoshi Ogiku、Hiroshi Ohmizu、Takashi Nishitani、Kazuhiko Kondo、Tameo Iwasaki

  DOI：10.1021/jo00103a029

  日期：1994.12

  The heterocyclic analogs 5a-f, 16, and 20 of 1-arylnaphthalene lignans were synthesized by Diels-Alder reactions of acetoxy aldehydes 11a-f, 14, and 18 with dimethyl acetylenedicarboxylate. A pathway for formation of 5a-f, 16, and 20 through the intermediacy of heteroaromatic isobenzofurans derived from acetoxy aldehydes is discussed.