N-benzyl-3-oxypyridinium betaine | 54429-89-9

• 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: N-benzyl-3-oxypyridinium betaine
• 英文别名: 1-benzyl-3-hydroxy-pyridinium betaine；1-benzyl-pyridinium-3-olate；1-Benzyl-3-hydroxy-pyridinium-betain；1-Benzylpyridin-1-ium-3-olate
• CAS: 54429-89-9
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: HYGDJRVXHVXONK-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-oxypyridinium betaine 在 4-二甲氨基吡啶 、 cesium fluoride 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 38.0h， 生成 12-benzyl-10-(hydroxymethyl)-12-azatricyclo[6.3.1.02,7]dodeca-2,4,6,10-tetraen-9-one
  参考文献：
  名称：

  Aryne cycloaddition with 3-oxidopyridinium species

  摘要：

  使用小林苯炔前体研究了芳炔与3-氧化吡啶铵物种的[3 + 2]环加成反应。该反应在温和条件下产生了双环[3.2.1]骨架。此外，还观察到了一种[7 + 2]环加成模式，随之发生吡啶环开环事件。

  DOI：

  10.1039/c2ob26519b
• 作为产物：
  描述：

  3-羟基吡啶 在 sodium methylate 作用下， 以 甲醇 、 丙醇 为溶剂， 生成 N-benzyl-3-oxypyridinium betaine
  参考文献：
  名称：

  通过1,3-偶极环加成反应固相合成功能化的托烷衍生物

  摘要：

  3-氧化吡啶鎓甜菜碱在固相上的活化烯烃上的1,3-偶极环加成反应会导致树脂结合的8-氮杂双环[3.2.1]辛烯酮发生进一步的转化，例如亲核试剂的1,4-加成。在碘化钾存在下，使用酰氯实现苄基连接基的裂解，得到取代的托烷衍生物。

  DOI：

  10.1016/s0040-4039(01)00565-2

文献信息

• [EN] FUSED TRICYCLIC PYRAZOLO[1, 5-A]PYRIMIDINES, METHODS FOR PREPARATION AND USES THEREOF<br/>[FR] PYRAZOLO[1,5-A]PYRIMIDINES TRICYCLIQUES CONDENSÉES, PROCÉDÉS POUR LES PRÉPARER ET LEURS UTILISATIONS
  申请人：WYETH CORP

  公开号：WO2009108827A1

  公开（公告）日：2009-09-03

  Fused, tricyclic pyrazolo1,5-a]pyrimidine compounds of formula A or of formula B: and pharmaceutically acceptable salts thereof are described, which selectively inhibit Raf kinase activity and are useful for treating disorders mediated by certain Raf kinases.

  描述了公式A或公式B的融合的、三环的吡唑并1,5-a]嘧啶化合物，以及其药学上可接受的盐，这些化合物选择性地抑制Raf激酶活性，并且适用于治疗由某些Raf激酶介导的疾病。
• Synthesis of the 6- and 7-hydroxylated cocaines and pseudococaines
  作者：A.P. Kozikowski、D. Simoni、S. Manfredini、M. Roberti、J. Stoelwinder

  DOI：10.1016/0040-4039(96)01123-9

  日期：1996.7

  In efforts aimed at further exploration of our finding that functionalization of the two-carbon bridge of cocaine can lead to a weak antagonist of cocaine, we report a route to the 6- and 7-hydroxylated analogues by use of the Willstätter synthesis. The hydroxylated derivatives can in principle be used to gain access to a diverse library of 6- and 7-functionalized cocaine analogues.

  为了进一步探索我们的发现，即可卡因的二碳桥可能导致弱的可卡因拮抗剂，我们报告了使用Willstätter合成法合成6-和7-羟基化类似物的途径。羟基化的衍生物原则上可用于获得6-和7-官能化的可卡因类似物的多样化文库。
• N-Substituted-3-oxypyridyl Betaines
  作者：Seymour L. Shapiro、Kurt Weinberg、Louis Freedman

  DOI：10.1021/ja01528a030

  日期：1959.10
• 6β-Acetoxynortropane:  A Potent Muscarinic Agonist with Apparent Selectivity toward M₂-Receptors
  作者：Xue-Feng Pei、Tara H. Gupta、Barbara Badio、W. L. Padgett、John W. Daly

  DOI：10.1021/jm9705115

  日期：1998.6.1

  A series of tropane derivatives, related in structure to baogongteng A (1), an alkaloid from a Chinese herb, were synthesized. 6 beta-Acetoxynortropane (5) had weak affinity (K-i 22 mu M) for central (M-1) muscarinic receptors in a [H-3]quinuclidinyl benzilate binding assay but had extremely high affinity (K-i 2.6 nM) and selectivity for M-2-muscarinic receptors expressed in CHO cells. It had 13-fold lower affinity for M-4-receptors, 260-fold lower affinity for M-3-receptors, and 8200-fold lower affinity for M-1-receptors expressed in CHO cells. The 6 beta-carbomethoxy analogue (14) of baogongteng A had only weak affinity for M-2-muscarinic receptors, as did 6 beta-carbomethoxynortropane (13) and 6 beta-acetoxytropane (4). In transfected CHO cells, 6 beta-acetoxynortropane (5) was an agonist at M-2-receptors, based on a GTP-elicited decrease in affinity, and a full agonist with an IC50 of 11 nM at M-4-receptors, based on inhibition of cyclic AMP accumulation, while being a full agonist at M-1-receptors with an EC50 Of 23 nM and a partial agonist at M-3-receptors with an EC50 Of 3.6 nM, based in both cases on stimulation of phosphoinositide breakdown. All of the 16 tropane derivatives had weak affinities for central alpha(4) beta(2)-nicotinic receptors with 6 beta-carbomethoxynortropane (13) having the highest affinity, which was still 150-fold less than that of nicotine. 6 beta-carbomethoxynortropane (5) represents a potent muscarinic agonist with apparent selectivity toward M-2-receptors.
• Structure of the Calystegines: New alkaloids of the nortropane family.
  作者：P.-H. Ducrot、J.Y. Lallemand

  DOI：10.1016/s0040-4039(00)97494-x

  日期：1990.1