2-(hydroxymethyl)-6-(dimethylaminomethyl)pyridine | 78442-43-0

• 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-(hydroxymethyl)-6-(dimethylaminomethyl)pyridine
• 英文别名: 6-dimethylaminomethyl-2-hydroxymethylpyridine；[6-[(dimethylamino)methyl]pyridin-2-yl]methanol
• CAS: 78442-43-0
• 化学式: C₉H₁₄N₂O
• 分子量: 166.223
• InChiKey: BLLMGCAOTCVTMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-6-(dimethylaminomethyl)pyridine 、 (N,N,N',N'-tetramethylethylenediamine)Pd(CH3)(acetonitrile) trifluoromethanesulfonate 以 丙酮 为溶剂， 生成 methyl[2-(hydroxymethyl)-6-((dimethylamino)methyl)pyridine](N,N,N',N'-tetramethylethylenediamine)palladium(II) trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis and Structural Studies of Ionic Monoorganopalladium(II) Complexes with Tridentate Nitrogen-Donor Ligands

  摘要：

  Ionic palladium(II) complexes of the types [PdCl(N-N'-N'')]Cl and [PdR(N-N'-N'')]OTf, with R = Me or aryl, N-N'-N'' = tridentate nitrogen donor ligand, and OTf = trifluoromethane-sulfonate (triflate), have been prepared. The tridentate nitrogen-donor ligands used are 2,6-bis[(dimethylamino)methyl]pyridine (NNN), N,N,N'-trimethyl-N'-(2-picolyl)ethylenediamine (pico), and N,N,N',N'',N''-pentamethyldiethylenetriamine (pmdeta). The chloro derivatives (3-5a) were obtained as yellow ionic complexes in excellent yields (81-93%). Crystals of 4a were obtained from methanol/diethyl ether and are monoclinic, space group P2(1)/c (No. 14), a = 15.0760(7) angstrom, b = 7.4468(8) angstrom, c = 13.553(2) angstrom, beta = 115.653(6)-degrees, and Z = 4. Refinement converged at R = 0.0325 (wR2 = 0.0663). The molecular structure shows a four-coordinate palladium center surrounded by the terdentate bound pico ligand and a chloride anion. There is no interaction of the palladium center with the second chloride anion (Pd-Cl2 greater-than-or-equal-to 4.2617 angstrom). The Pd-NMe bond distance (2.023(3) angstrom) is relatively short and is accompanied by a small trans N-Pd-N bond angle (168.03(12)-degrees). The methyl derivatives (3-5b) were also obtained in good yield (79-91%) via reaction of PdIMe(tmeda) (tmeda = N,N,N',N'-tetramethylethylenediamine) with silver trifluoromethanesulfonate and the ligand. An alternative route, starting from PdMe2(tmeda), is reported for the synthesis of [PdMe(NNN)OTf (3b). Crystals of 3b were obtained from methanol/diethyl ether and are monoclinic, space group P2(1)/a (No. 14), a = 7.738(l) angstrom, b = 21.280(2) angstrom, c = 11.399(1) angstrom, beta = 92.05(1)-degrees, and Z = 4. Refinement converged at R = 0.066 (R(w) = 0.065). The molecular structure of Sb shows a terdentate coordination of the NNN ligand to the metal, with a relatively short Pd-N' bond distance (1.996(8) angstrom) and small N-Pd-N bond angle (161.7(3)-degrees). Yellow crystals of [PdMe(ONN')(tmeda)]OTf (8), with ONN' = 2-(hydroxymethyl)-6-[(dimethylamino)methyl]pyridine (7), were accidentally obtained from the reaction of [PdMe(MeCN)(tmeda)]OTf (I) with an impure sample of the NN'N ligand, containing the ONN' ligand. The molecular structure of 8 shows the ONN' ligand monodentate coordinated to the metal via its pyridyl nitrogen donor whereas the NMe2 and OH functionalities are free. The triflate anion is hydrogen bonded to the hydroxymethyl group with OH=O-(SO2CF3) = 2.759(3) angstrom and O-H-O = 173(4)-degrees. Crystals of [PdMe(ONN')(tmeda)]OTf (8) are triclinic, space group P1BAR (No. 2), a = 9.7902(14) angstrom, b = 10.0555(15) angstrom, c = 12.362(2) angstrom, alpha = 75.828(12)-degrees, beta = 81.234(12)-degrees, gamma = 84.836(11)-degrees, and Z = 2. Refinement converged at R = 0.032 (R(w) = 0.040). The first examples of simple arylpalladium(II) cations containing tridentate ligands were obtained m moderate to high yield (35-95%). The aryl groups studied differ in both steric and electronic properties. Conformational analysis by NMR of the NCCN moieties of the pico and pmdeta containing complexes showed the five-membered chelate rings in the complexes to occur selectively in one of the two possible conformations. The rotational-energy barriers of the aryl groups have been studied as a function of the ligand and were shown to increase in the order NNN < pico < pmdeta.This is explained in terms' of the positioning and orientation of the pyridyl and NMe2 groups around the metal center. The aryl rotation is found to be blocked in ortho-substituted aryl complexes, leading to atropisomerism in the pmdeta complex.

  DOI：

  10.1021/om00020a043
• 作为产物：
  描述：

  methyl 6-(dimethylcarbamoyl)pyridine-2-carboxylate 、 Lithium aluminium hydride 、 Sodium sulfate-III 在 氮 、 二氯甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以to give 5.2 g of the title compound的产率得到2-(hydroxymethyl)-6-(dimethylaminomethyl)pyridine
  参考文献：
  名称：

  Substituted 1,2,5-thiadiazole derivatives

  摘要：

  该专利涉及一种组成式为##STR1##的组织胺H.sub.2-拮抗剂，其中p为1或2；R.sup.1为羟基，氨基，取代氨基或通过其氮原子连接的5-至9-成员完全饱和的含氮杂环；m为0到2的整数；n为2到4的整数；Z为硫，氧或亚甲基；而A为可选的取代苯基，咪唑基，噻唑基，异噻唑基，噁唑基，异噁唑基，三唑基，噻二唑基，氧杂二唑基，呋喃基，噻吩基或吡啶基；以及其非毒性医药上可接受的盐，水合物，溶剂合物或N-氧化物是新的抗溃疡剂。还公开了其中间体和制备方法。

  公开号：

  US04380639A1

文献信息

• Chemical compounds
  申请人：Bristol-Myers Company

  公开号：US04380638A1

  公开（公告）日：1983-04-19

  Histamine H.sub.2 -antagonists of the formula ##STR1## wherein p is 1 or 2; R.sup.1 is hydroxy, amino, substituted amino or a 5- to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2; n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anti-ulcer agents. Intermediates and processes for their preparation are disclosed.

  组成式为##STR1##的组胺H.sub.2-拮抗剂，其中p为1或2；R.sup.1为羟基，氨基，取代氨基或通过其氮原子连接的5-至9-成员完全饱和的含氮杂环；m为0至2的整数；n为2至4的整数；Z为硫，氧或亚甲基；而A为可选取代的苯基，咪唑基，噻唑基，异噻唑基，噁唑基，异噁唑基，三唑基，噻二唑基，氧杂噻二唑基，呋喃基，噻吩基或吡啶基环；以及其非毒性药学上可接受的盐，水合物，溶剂合物或N-氧化物是新的抗溃疡剂。公开了其中间体和制备方法。
• Thiadiazole histamine H.sub.2 -antagonists
  申请人：Bristol-Myers Company

  公开号：US04471122A1

  公开（公告）日：1984-09-11

  Histamine H.sub.2 -antagonists of the formula ##STR1## wherein p is 1 or 2; R.sup.1 is hydroxy, amino, substituted amino or a 5- to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2; n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anti-ulcer agents. Intermediates and processes for their preparation are disclosed.

  该专利描述了一种新型抗溃疡药物，即公式为##STR1##的组织胺H.sub.2-拮抗剂，其中p为1或2；R.sup.1为羟基、氨基、取代氨基或通过其氮原子连接的5-至9-成员完全饱和的含氮杂环；m为0至2的整数；n为2至4的整数；Z为硫、氧或亚甲基；A为可选取代的苯基、咪唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、三唑基、噻二唑基、氧杂二唑基、呋喃基、噻吩基或吡啶基环；以及其无毒的药学上可接受的盐、水合物、溶剂化合物或N-氧化物。还公开了其中间体和制备方法。
• Histamine H.sub.2 -antagonists
  申请人：Bristol-Myers Company

  公开号：US04510309A1

  公开（公告）日：1985-04-09

  Histamine H.sub.2 -antagonists of the formula ##STR1## wherein p is 1 or 2; R.sup.1 is hydroxy, amino, substituted amino or a 5- to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2, n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anti-ulcer agents. Intermediates and processes for their preparation are disclosed.

  组成式为##STR1##的组胺H.sub.2-拮抗剂，其中p为1或2;R.sup.1为羟基，氨基，取代氨基或通过其氮原子连接的5-至9-成员完全饱和的含氮杂环环；m为0至2的整数，n为2至4的整数；Z为硫，氧或亚甲基；而A为可选取代的苯基，咪唑基，噻唑基，异噻唑基，噁唑基，异噁唑基，三唑基，噻二唑基，氧化二唑基，呋喃基，噻吩基或吡啶基；以及其非毒性药用可接受的盐，水合物，溶剂化合物或N-氧化物是新的抗溃疡剂。还公开了其中间体和制备过程。
• 3,4-Disubstituted-1,2,5-thiadiazole-1-oxide compounds
  申请人：Bristol-Myers Company

  公开号：US04374248A1

  公开（公告）日：1983-02-15

  Histamine H.sub.2 -antagonists of the formula ##STR1## wherein p is 1 or 2; R.sup.1 is hydroxy, amino, substituted amino or a 5- to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2; n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anit-ulcer agents. Intermediates and processes for their preparation are disclosed.

  结构式为 ##STR1## 的组胺H.sub.2-拮抗剂，其中p为1或2；R.sup.1为羟基，氨基，取代氨基或通过其氮原子连接的具有5-至9-成员完全饱和的含氮杂环环；m为0至2的整数；n为2至4的整数；Z为硫，氧或亚甲基；A为可选取代的苯基，咪唑基，噻唑基，异噻唑基，噁唑基，异噁唑基，三唑基，噻二唑基，氧杂二唑基，呋喃基，噻吩基或吡啶基环；以及其非毒性药学上可接受的盐，水合物，溶剂合物或N-氧化物是新型抗溃疡剂。公开了它们的中间体和制备方法。
• Pharmaceutical compositions
  申请人：Bristol-Myers Company

  公开号：EP0099121A2

  公开（公告）日：1984-01-25

  Enhanced antiulcer activity is obtained in warm-blooded animals by the concomitant administration of the pepsin complexing agent, pepstatin, and an histamine H2-receptor antagonist of the formula wherein A, m, Z, n, p and R1 are as defined herein. Concomitant administration of the two entities reduces the amount of histamine H2-receptor antagonist necessary for treatment, thereby decreasing its side-effect liability.

  在温血动物中，同时服用胃蛋白酶络合剂胃舒平和组胺 H2 受体拮抗剂，可增强抗溃疡活性。 其中 A、m、Z、n、p 和 R1 如本文所定义。同时使用这两种物质可减少治疗所需的组胺 H2 受体拮抗剂的用量，从而降低其副作用。