Methyl-[1-methyl-piperidin-(2E)-ylidene]-sulfonium; iodide

• 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: Methyl-[1-methyl-piperidin-(2E)-ylidene]-sulfonium; iodide
• 化学式: C₇H₁₄NS*I
• 分子量: 271.165
• InChiKey: XVNFUEQNMHLHQN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.42
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  3.01
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  Methyl-[1-methyl-piperidin-(2E)-ylidene]-sulfonium; iodide 在 potassium tert-butylate 作用下， 生成 1-Methyl-2-methylmercapto-1,4,5,6-tetrahydro-pyridin
  参考文献：
  名称：

  Coupling-Isomerization−N,S-Ketene Acetal-Addition SequencesA Three-Component Approach to Highly Fluorescent Pyrrolo[2,3-b]pyridines, [1,8]Naphthyridines, and Pyrido[2,3-b]azepines

  摘要：

  Annelated 2-amino pyridines such as pyrrolo[2,3-b]pyridines, [1,8]naphthyridines, and pyrido[2,3-b]azepines can be synthesized in moderate to good yields in a consecutive one-pot three-component process by a coupling-isomerization-enamine-addition-cyclocondensation sequence of an electron-poor (hetero)aryl halide, a terminal propargyl N-tosylamine, and an N,S-ketene acetal. After the coupling-isomerization sequence, a Diels-Alder reaction with inverse electron demand of the intermediate enimine and the N,S-ketene acetal and subsequent aromatization furnish annelated 2-amino pyridines 4 that were unambiguously characterized by numerous X-ray structure analyses. These heterocycles are highly fluorescent and partially pH sensitive, and their electronic structure was studied with spectroscopic and computational methods.

  DOI：

  10.1021/jo0602726
• 作为产物：
  描述：

  1-甲基-2-哌啶酮 在 劳森试剂 作用下， 生成 Methyl-[1-methyl-piperidin-(2E)-ylidene]-sulfonium; iodide
  参考文献：
  名称：

  Coupling-Isomerization−N,S-Ketene Acetal-Addition SequencesA Three-Component Approach to Highly Fluorescent Pyrrolo[2,3-b]pyridines, [1,8]Naphthyridines, and Pyrido[2,3-b]azepines

  摘要：

  Annelated 2-amino pyridines such as pyrrolo[2,3-b]pyridines, [1,8]naphthyridines, and pyrido[2,3-b]azepines can be synthesized in moderate to good yields in a consecutive one-pot three-component process by a coupling-isomerization-enamine-addition-cyclocondensation sequence of an electron-poor (hetero)aryl halide, a terminal propargyl N-tosylamine, and an N,S-ketene acetal. After the coupling-isomerization sequence, a Diels-Alder reaction with inverse electron demand of the intermediate enimine and the N,S-ketene acetal and subsequent aromatization furnish annelated 2-amino pyridines 4 that were unambiguously characterized by numerous X-ray structure analyses. These heterocycles are highly fluorescent and partially pH sensitive, and their electronic structure was studied with spectroscopic and computational methods.

  DOI：

  10.1021/jo0602726

文献信息

• Synthesis of 5-Amino-4-(2-azacycloalkylidene)-2-phenyl-2,4-dihydro-3<i>H</i>-pyrazol-3-ones
  作者：Konstantin Nazarenko、Sergey Bova、Vitaliy Polovinko、Andrey Tolmachev

  DOI：10.1055/s-0028-1083183

  日期：——

  The reaction 5-amino-2-phenyl-3,4-dihydro-3H-pyrazol-3-one with activated lactams (lactim ethers, lactam acetals, and methylthioalkylidene iminium salts) was investigated. It occurs on the active methylene group of 5-amino-2-phenyl-3,4-dihydro-3H-pyrazol-3-one to furnish cyclic enamines, 5-amino-4-(2-azacycloalkylidene)-2-phenyl-2,4-dihydro-3H-pyrazol-3-ones and 5-amino-4-(1-methyl-2-azacycloalkylidene)-2-phenyl-2,4-dihydro-3H-pyrazol-3-ones.

  研究了5-氨基-2-苯基-3,4-二氢-3H-吡唑-3-酮与活化的内酰胺（内酰胺醚、内酰胺缩醛和甲硫基烯亚胺盐）的反应。反应发生在5-氨基-2-苯基-3,4-二氢-3H-吡唑-3-酮的活性亚甲基上，生成环状烯胺、5-氨基-4-(2-氮杂环烷亚基)-2-苯基-2,4-二氢-3H-吡唑-3-酮和5-氨基-4-(1-甲基-2-氮杂环烷亚基)-2-苯基-2,4-二氢-3H-吡唑-3-酮。
• Renault, Annales de Chimie (Cachan, France), 1955, vol. <12> 10, p. 135,144
  作者：Renault

  DOI：——

  日期：——
• Substituted 2-Iminopiperidines as Inhibitors of Human Nitric Oxide Synthase Isoforms
  作者：R. Keith Webber、Suzanne Metz、William M. Moore、Jane R. Connor、Mark G. Currie、Kam F. Fok、Timothy J. Hagen、Donald W. Hansen,、Gina M. Jerome、Pamela T. Manning、Barnett S. Pitzele、Mihaly V. Toth、Mahima Trivedi、Mark E. Zupec、F. Siong Tjoeng

  DOI：10.1021/jm9705059

  日期：1998.1.1

  A series of analogues of 2-iminopiperidine have been prepared and shown to be potent inhibitors of the human nitric oxide synthase (NOS) isoforms. Methyl substitutions on the 4-position (3) or 4- and 6-positions (8) afforded the most potent analogues. These compounds exibited IC50 values of 0.1 and 0.08 mu M, respectively, for hiNOS inhibition. Substitution with cyclohexylmethyl at the 6-position (13) afforded an inhibitor that showed the best selectivity for hiNOS versus heNOS (heNOS IC50/hiNOS IC50 = 64). Following oral administration, inhibitors were found to decrease serum nitrite/nitrate levels in an in vivo rat endotoxin assay. This series of 2-iminopiperidines were prepared via the described synthetic methodologies. The effect of ring substitutions on potency and selectivity for this class of cyclic amidines as NOS inhibitors is described.
• Methods for converting N-alkyl lactams to vinylogous urethanes and vinylogous amides via(methylthio)alkylideniminium salts
  作者：Mary M. Gugelchuk、David J. Hart、Yeun-Min Tsai

  DOI：10.1021/jo00331a018

  日期：1981.8
• Kostir; Padr, Chemicke Listy, 1946, vol. 40, p. 276,278
  作者：Kostir、Padr

  DOI：——

  日期：——