6-甲基-2-吡啶甲醛1-氧化物 | 100960-01-8

• 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
• 中文名称: 6-甲基-2-吡啶甲醛1-氧化物
• 英文名称: 6-methyl-1-oxypyridine-2-carbaldehyde
• 英文别名: 6-methyl-pyridine-2-carbaldehyde-1-oxide；6-Methyl-pyridin-2-carbaldehyd-1-oxid；6-Methylpyridine-2-carbaldehyde 1-oxide；6-methyl-1-oxidopyridin-1-ium-2-carbaldehyde
• CAS: 100960-01-8
• 化学式: C₇H₇NO₂
• 分子量: 137.138
• InChiKey: PWKNOZQGVCXXLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-甲基-2-吡啶甲醛1-氧化物 在 potassium cyanide 作用下， 生成 2-hydroxy-1,2-bis-(6-methyl-1-oxy-[2]pyridyl)-ethanone
  参考文献：
  名称：

  Mathes; Sauermilch, Justus Liebigs Annalen der Chemie, 1958, vol. 618, p. 152,155

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲基-2-吡啶基甲醇 在 selenium(IV) oxide 、 水 、 双氧水 、 溶剂黄146 作用下， 生成 6-甲基-2-吡啶甲醛1-氧化物
  参考文献：
  名称：

  Furukawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 957,959

  摘要：

  DOI：

文献信息

• Bis(oxazoline) Lewis Acid Catalyzed Aldol Reactions of PyridineN-Oxide Aldehydes—Synthesis of Optically Active 2-(1-Hydroxyalkyl)pyridine Derivatives: Development, Scope, and Total Synthesis of an Indolizine Alkaloid
  作者：Aitor Landa、Anna Minkkilä、Gonzalo Blay、Karl Anker Jørgensen

  DOI：10.1002/chem.200501475

  日期：2006.4.24

  A new, short, and simplified procedure for the synthesis of optically active pyridine derivatives from pro-chiral pyridine-N-oxides is presented. The catalytic and asymmetric Mukaiyama aldol reaction between ketene silyl acetals and 1-oxypyridine-2-carbaldehyde derivatives catalyzed by chiral copper(II)-bis(oxazoline) complexes gave optically active 2-(hydroxyalkyl)- and 2-(anti-1,2-dihydroxyalkyl)pyridine

  提出了一种新的，短而简化的从前手性吡啶-N-氧化物合成旋光吡啶衍生物的方法。烯酮甲硅烷基缩醛与手性铜（II）-双（恶唑啉）配合物催化的1-氧吡啶-2-甲醛反应之间的催化和不对称的Mukaiyama羟醛反应，得到旋光的2-（羟烷基）-和2-（反-1， 2-二羟基烷基）吡啶衍生物，具有良好的收率和非对映选择性，并具有优异的对映选择性，最高达99％对映体过量。作为所开发方法的合成应用，提供了非天然吲哚嗪生物碱的不对称全部合成的完整说明。
• 3-Cyanoquinoline inhibitors of Tpl2 kinase and methods of making and using the same
  申请人：Green Jeffrey Neal

  公开号：US20060264460A1

  公开（公告）日：2006-11-23

  The present invention provides compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , m and n are defined as described herein. The invention also provides methods of making the compounds of formula (I), and methods of treating inflammatory diseases, such as rheumatoid arthritis, in a mammal comprising administering a therapeutically effective amount of a compound of formula (I) to the mammal.

  本发明提供了如下式（I）的化合物及其药用可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、R8、m和n的定义如本文所述。该发明还提供了制备如式（I）化合物的方法，以及治疗炎症性疾病（如类风湿性关节炎）的方法，包括向哺乳动物施用如式（I）化合物的治疗有效量。
• Asymmetric Synthesis of Adjacent Tri‐ and Tetrasubstituted Carbon Stereocenters: Organocatalytic Aldol Reaction of an Hydantoin Surrogate with Azaarene 2‐Carbaldehydes
  作者：June Izquierdo、Noémie Demurget、Aitor Landa、Tore Brinck、Jose M. Mercero、Peter Dinér、Mikel Oiarbide、Claudio Palomo

  DOI：10.1002/chem.201902817

  日期：2019.9.20

  A bifunctional amine/squaramide catalyst promoted direct aldol addition of an hydantoin surrogate to pyridine 2-carbaldehyde N-oxides to afford adducts bearing two vicinal tertiary/quaternary carbons in high diastereo- and enantioselectivity (d.r. up to >20:1; ee up to 98 %) is reported. Acid hydrolysis of adducts followed by reduction of the N-oxide group yields enantiopure carbinol-tethered quaternary

  双功能胺/方胺催化剂可将乙内酰脲替代物直接直接羟醛添加到吡啶2-甲醛N-氧化物上，从而以高非对映和对映选择性（dr高达> 20：1; ee高达报告了98％）。加合物的酸水解，然后还原N-氧化物基团，生成对映体纯的甲醇系链的季内乙内酰脲-氮杂芳烃，具有稠密的官能化骨架。反应的势能面（B3LYP / 6-31 + G（d）+ CPCM（二氯甲烷））的DFT研究与不同催化剂的活性相关并支持分子内氢键辅助的过渡中方酸酰胺部分的活化催化反应的状态。
• N-Oxide compounds useful in the treatment of cardiovascular ailments
  申请人：Ciba-Geigy Corporation

  公开号：US04497808A1

  公开（公告）日：1985-02-05

  The present invention relates to novel N-oxide compounds that have cardiovascular properties, especially antihypertensive activity, and that correspond to the formula ##STR1## in which Py represents an unsubstituted or substituted N-oxidopyridyl radical, R.sub.1 represents hydrogen or unsubstituted or substituted lower alkyl, one of the radicals R.sub.2 and R.sub.3 represents lower alkyl and the other represents hydrogen; lower alkyl; lower alkyl containing free, etherified or esterified hydroxy, oxo, functionally modified carboxy or free or substituted amino or imino; functionally modified carboxy; or free or substituted amino, it being possible for an amino group R.sub.2 or R.sub.3 to be bonded to a lower alkyl radical R.sub.1 or, if R.sub.2 or R.sub.3 represents, for example, hydroxy-lower alkyl, for this hydroxy-lower alkyl, together with the adjacent acyl radical Ac.sub.1 or Ac.sub.2, to form a 2-oxa-1-oxo-lower alkylene radical, the carbonyl group of which is bonded to the 3- or 5-ring carbon atom of the 1,4-dihydropyridine ring, and each of the groups Ac.sub.1 and Ac.sub.2 represents, independently of the other, the acyl radical of an acid, and salts of compounds of the formula I having salt-forming groups, processes for the manufacture of these compounds, the use of these compounds and their salts, and pharmaceutical preparations which contain these compounds and salts, as antihypertensive agents and coronary dilators for the treatment of cardiovascular conditions, such as hypertonia, vascular constrictions, Angina pectoris and cardiac insufficiency.

  本发明涉及一种具有心血管特性，特别是降压活性的新型N-氧化物化合物，其符合以下式子：##STR1## 其中，Py代表未取代或取代的N-氧化吡啶基团，R1代表氢或未取代或取代的较低烷基，R2和R3中的一个代表较低烷基，另一个代表氢、较低烷基、含有自由、醚化或酯化羟基、氧代基、功能修饰羧基或自由或取代的氨基或亚氨基的较低烷基、功能修饰羧基或自由或取代的氨基，其中R2或R3的氨基可以与较低烷基基团R1结合，或者如果R2或R3代表例如羟基-较低烷基，则该羟基-较低烷基可以与相邻的酰基Ac1或Ac2一起形成2-氧杂-1-氧代-较低烷基基团，其羰基与1,4-二氢吡啶环的3-或5-环碳原子结合，Ac1和Ac2各自独立地表示酸的酰基基团，以及具有盐基的式I化合物的盐，这些化合物的制备方法，以及这些化合物和盐的使用和制备的药物制剂，作为降压剂和冠状动脉扩张剂，用于治疗心血管疾病，例如高血压、血管收缩、心绞痛和心力衰竭。
• 3-CYANOQUINOLINE INHIBITORS OF TPL2 KINASE AND METHODS OF MAKING AND USING THE SAME
  申请人：Wyeth

  公开号：EP1888529A2

  公开（公告）日：2008-02-20