2-Bromopyridine-3-carbaldehyde dimethyl acetal | 123694-62-2

• 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: 2-Bromopyridine-3-carbaldehyde dimethyl acetal
• 英文别名: Pyridine, 2-bromo-3-(dimethoxymethyl)-；2-bromo-3-(dimethoxymethyl)pyridine
• CAS: 123694-62-2
• 化学式: C₈H₁₀BrNO₂
• 分子量: 232.077
• InChiKey: AJDLUSUIIVLQKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  264.1±35.0 °C(Predicted)
• 密度：
  1.435±0.06 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：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Bromopyridine-3-carbaldehyde dimethyl acetal 在 正丁基锂 、 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 16.82h， 生成 1'-benzyl-5-methoxy-5H-spiro[furo[3,4-b]pyridine-7,4'-piperidine]
  参考文献：
  名称：

  Synthesis and σ receptor affinity of regioisomeric spirocyclic furopyridines

  摘要：

  In order to investigate systematically the effect of the position of the pyridine N-atom on the σ1 receptor affinity four regioisomeric furopyridines 2a-d were synthesized and pharmacologically evaluated. The key steps of the synthesis comprise bromine/lithium exchange at regioisomeric bromopyridinecarbaldehyde acetals 7a-d, subsequent addition to 1-benzylpiperidin-4-one and cyclization. The regioisomeric acetals 7a-d were obtained either by o-metalation of bromopyridines 5b and 5c or by oxidation of bromopicolines 3a and 3d. In radioligand binding studies the regioisomeric furopyridines 2a-d showed 7- to 12-fold lower σ1 affinity than the benzofuran analog 1. The reduced σ1 affinity of the furopyridines 2a-d is explained with the reduced electron density of the pyridine ring. Since the four regioisomeric furopyridines show almost the same σ1 affinity (Ki = 4.9-10 nM), a directed interaction of the pyridine N-atom with the receptor protein can be excluded.

  DOI：

  10.1016/j.ejmech.2014.06.073
• 作为产物：
  描述：

  2-溴-3-甲基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 、 calcium carbonate 、 过氧化苯甲酰 作用下， 以 甲醇 、 四氯化碳 、 水 为溶剂， 反应 35.0h， 生成 2-Bromopyridine-3-carbaldehyde dimethyl acetal
  参考文献：
  名称：

  Synthesis and σ receptor affinity of regioisomeric spirocyclic furopyridines

  摘要：

  In order to investigate systematically the effect of the position of the pyridine N-atom on the σ1 receptor affinity four regioisomeric furopyridines 2a-d were synthesized and pharmacologically evaluated. The key steps of the synthesis comprise bromine/lithium exchange at regioisomeric bromopyridinecarbaldehyde acetals 7a-d, subsequent addition to 1-benzylpiperidin-4-one and cyclization. The regioisomeric acetals 7a-d were obtained either by o-metalation of bromopyridines 5b and 5c or by oxidation of bromopicolines 3a and 3d. In radioligand binding studies the regioisomeric furopyridines 2a-d showed 7- to 12-fold lower σ1 affinity than the benzofuran analog 1. The reduced σ1 affinity of the furopyridines 2a-d is explained with the reduced electron density of the pyridine ring. Since the four regioisomeric furopyridines show almost the same σ1 affinity (Ki = 4.9-10 nM), a directed interaction of the pyridine N-atom with the receptor protein can be excluded.

  DOI：

  10.1016/j.ejmech.2014.06.073

文献信息

• Visible-Light-Induced Tandem Radical Addition–Cyclization of Alkenyl Aldehydes Leading to Indanones and Related Compounds
  作者：Danyang Lu、Yimei Wan、Lichun Kong、Gangguo Zhu

  DOI：10.1021/acs.orglett.7b01162

  日期：2017.6.2

  Herein we describe a novel, visible light-induced tandem radical addition–cyclization of alkenyl aldehydes with α-bromocarbonyl compounds. A set of cyclic ketones, including indanones, cyclopentenones, 3,4-dihydronaphthalen-1(2H)-ones, and chroman-4-ones, are synthesized at room temperature with high efficiency and good functional group compatibility. It represents the first report on the catalytic

  在此我们描述了一种新，用α链烯醛的可见光诱导的串联基加环化-溴代化合物。在室温下以高效率和良好的官能团相容性合成了一组环酮，包括茚满酮，环戊烯酮，3,4-二氢萘-1（2 H）-酮和苯并吡喃-4-酮。它代表了有关未活化烯烃催化1,2-酰基烷基化的第一份报告。
• Biphenyl derivatives, preparation method, pharmaceutical compositions comprising them and use
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：EP0316939A2

  公开（公告）日：1989-05-24

  Biphenyl derivative of the formula: wherein R¹ is hydrogen atom or a lower alkoxycarbonyl group and R² is a lower alkoxycarbonyl group, or R¹ and R² are combined together to form a group of the formula: each of R³ and R⁴ is a lower alkoxy group; and Ring A is a substituted or unsubstituted sulfur-containing or nitrogen-containing heterocyclic ring, and a pharmaceutically acceptable salt thereof are disclosed. Said biphenyl derivative (I) and its salt have excellent hypolipidemic activity and are useful for treatment or prophylaxis of hyperlipidemia and/or arteriosclerosis.

  式中的联苯衍生物 其中 R¹ 是氢原子或低级烷氧羰基，R² 是低级烷氧羰基，或 R¹ 和 R² 结合在一起形成式中的基团： R³ 和 R⁴ 中的每一个都是低级烷氧基；环 A 是取代或未取代的含硫或含氮杂环，本发明公开了其药学上可接受的盐。所述联苯衍生物（I）及其盐具有优异的降脂活性，可用于治疗或预防高脂血症和/或动脉硬化。
• 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.
• US4952602A
  申请人：——

  公开号：US4952602A

  公开（公告）日：1990-08-28
• Synthesis and σ receptor affinity of regioisomeric spirocyclic furopyridines
  作者：Kengo Miyata、Dirk Schepmann、Bernhard Wünsch

  DOI：10.1016/j.ejmech.2014.06.073

  日期：2014.8

  In order to investigate systematically the effect of the position of the pyridine N-atom on the σ1 receptor affinity four regioisomeric furopyridines 2a-d were synthesized and pharmacologically evaluated. The key steps of the synthesis comprise bromine/lithium exchange at regioisomeric bromopyridinecarbaldehyde acetals 7a-d, subsequent addition to 1-benzylpiperidin-4-one and cyclization. The regioisomeric acetals 7a-d were obtained either by o-metalation of bromopyridines 5b and 5c or by oxidation of bromopicolines 3a and 3d. In radioligand binding studies the regioisomeric furopyridines 2a-d showed 7- to 12-fold lower σ1 affinity than the benzofuran analog 1. The reduced σ1 affinity of the furopyridines 2a-d is explained with the reduced electron density of the pyridine ring. Since the four regioisomeric furopyridines show almost the same σ1 affinity (Ki = 4.9-10 nM), a directed interaction of the pyridine N-atom with the receptor protein can be excluded.