3-(cyanomethyl)-1-methylpyridin-1-ium iodide | 5562-24-3

• 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: 3-(cyanomethyl)-1-methylpyridin-1-ium iodide
• 英文别名: 3-Cyanomethyl-1-methyl-pyridinium; iodide；2-(1-Methylpyridin-1-ium-3-yl)acetonitrile;iodide
• CAS: 5562-24-3
• 化学式: C₈H₉N₂*I
• 分子量: 260.077
• InChiKey: MGTIPWHBGWZTOR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.42
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(cyanomethyl)-1-methylpyridin-1-ium iodide 在 sodium tetrahydroborate 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 1-Methyl-3-(cyanomethyl)-1,2,5,6-tetrahydropyridine N-oxide
  参考文献：
  名称：

  Synthesis of 20-deethylsilicine from a second-generation 2-cyano-.DELTA.3-piperidine synthon

  摘要：

  The Zn2+ ion mediated reaction of the 2-cyano-DELTA3-piperidine 9a (X = SO2C6H5) with the silyl enol ether of Na-methyl-2-acetylindole (24) led to formation of compounds 29a,b (70%) resulting from introduction of the acetylindole moiety at the exocyclic (C-7) carbon center and migration of the phenylsulfonyl group from C-7 to C-4. In contrast, reaction of 2-Cyano-DELTA3-piperidine 9b (X = CN) with 24 gave the desired C-4 acetylindole-substituted products 36a,b (1:1.3 mixture; 72% overall yield). Attempts to cyclize intermediates 36 to the tetracyclic enamine 27 were unsuccessful. Alternatively, the Zn2+-catalyzed reaction of synthons 9a and 9b with indole gave the C-7 indole-substituted aminonitriles 37a,b and 38, respectively. These intermediates were converted to DELTA2-piperidine 40 on reaction with sodium dimethyl malonate and AgBF4. Stereoselective hydrogenation of the enamine double bond in 40 furnished the required cis 3,4-disubstituted piperidine 41, which was cyclized under acidic conditions to the target molecule, 20-deethylsilicine (20).

  DOI：

  10.1021/jo00050a012
• 作为产物：
  描述：

  3-吡啶乙腈 、 碘甲烷 以 甲苯 为溶剂， 反应 0.75h， 以95%的产率得到3-(cyanomethyl)-1-methylpyridin-1-ium iodide
  参考文献：
  名称：

  Synthesis of 20-deethylsilicine from a second-generation 2-cyano-.DELTA.3-piperidine synthon

  摘要：

  The Zn2+ ion mediated reaction of the 2-cyano-DELTA3-piperidine 9a (X = SO2C6H5) with the silyl enol ether of Na-methyl-2-acetylindole (24) led to formation of compounds 29a,b (70%) resulting from introduction of the acetylindole moiety at the exocyclic (C-7) carbon center and migration of the phenylsulfonyl group from C-7 to C-4. In contrast, reaction of 2-Cyano-DELTA3-piperidine 9b (X = CN) with 24 gave the desired C-4 acetylindole-substituted products 36a,b (1:1.3 mixture; 72% overall yield). Attempts to cyclize intermediates 36 to the tetracyclic enamine 27 were unsuccessful. Alternatively, the Zn2+-catalyzed reaction of synthons 9a and 9b with indole gave the C-7 indole-substituted aminonitriles 37a,b and 38, respectively. These intermediates were converted to DELTA2-piperidine 40 on reaction with sodium dimethyl malonate and AgBF4. Stereoselective hydrogenation of the enamine double bond in 40 furnished the required cis 3,4-disubstituted piperidine 41, which was cyclized under acidic conditions to the target molecule, 20-deethylsilicine (20).

  DOI：

  10.1021/jo00050a012

文献信息

• Crescent‐Shaped Carbazole Derivatives as Light‐Up Fluorescence Probes for G‐Quadruplex DNA and Live Cell Imaging
  作者：Yongqiang Kang、Chunying Wei

  DOI：10.1002/cbdv.202101030

  日期：2022.3

  distributed in the mitochondrion of living HepG2 cells, and a weak fluorescence signal is also observed in the nucleus for 4c. Given that the two compounds have the larger association constants to G-quadruplexes over to duplex and single-stranded DNA, we speculate that the fluorescence signals in cells may mainly be attributed to the compound/G-quadruplex DNA complexes.

  近年来，针对G-四链体的有机小分子荧光探针的研究受到广泛关注，因为G-四链体在各种生物学功能中发挥着重要作用。在此，我们报道了三种新月形咔唑衍生物（4a-4c），并研究了它们与单链、双链、G-四链和 i-基序 DNA 的相互作用。4b 和 4c 都具有 100 nm 以上的斯托克斯位移和低荧光强度，此外，它们对 G-四链体的亲和力比对其他 DNA 结构的亲和力更强。具有氰基乙烯基吡啶盐基团的图4b显示对G-四链体的特定发光荧光响应。FRET 和 CD 结果表明，4b 和 4c 都能够提高 G-四链体的稳定性并保持其拓扑结构，此外，它们诱导富含 G 的序列（bcl-2、HTG、和 KSS) 在 Na+ /K+ 游离缓冲液中折叠成 G-四链体。此外，CLSM图像表明4b和4c主要分布在活HepG2细胞的线粒体中，4c在细胞核中也观察到微弱的荧光信号。鉴于这两种化合物对 G-四链体的缔合常数大于双链和单链
• [EN] 1-AZABICYCLO[3.2.0]HEPT-2-ENE-2-CARBOXYLIC ACID COMPOUNDS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1992002521A1

  公开（公告）日：1992-02-20

  (EN) A compound of formula (I) in which R1 is carboxy, protected carboxy or carboxylato, R2 is hydroxy(lower)alkyl or protected hydroxy-(lower)alkyl, R3 is axetidinyl, pyrrolidinyl, imidazolinyl, tetrahydropyrimidinyl, piperidyl, 1,1-di(lower)alkylpiperidinio, 3-(lower)-alkyl-1-(2-imidazolinio), 3-[hydroxy-(lower)alkyl]-1-(2-imidazolinio) or 3-(lower)alkyl-1,4,5,6-tetrahydro-1-pyrimidinio; wherein each heterocyclic group may be substituted by one or more suitable substituent(s), R10 is hydrogen or lower alkyl, and A is lower alkylene, provided that when R3 is lower alkylpyrrolidinyl, then R10 is hydrogen, or a pharmaceutically acceptable salt thereof, which is useful as an antimicrobial agent.(FR) L'invention se rapporte à un composé représenté par la formule [I]; où: R1 représente un carboxy, un carboxy protégé ou un carboxylato; R2 représente un hydroxyalkyle(inférieur) ou un hydroxyalkyl(inférieur); R3 représente un azétidinyle, un pyrrolidinyle, un imidazolinyle, un tétrahydropyrimidinyle, un pipéridyle, un 1,1-dialkylepipéridinio(inférieur), un 3-alkyle(inférieur)-1-(2-imidazolinio), un 3-[hydroxyalkyle(inférieur)]-1-(2-imidazolinio) ou un 3-alkyle(inférieur)-1,4,5,6-tétrahydro-1-pyrimidinio, ou chaque groupe hétérocyclique peut être substitué par un ou plusieurs substituants appropriés; R10 représente hydrogène ou un alkyle inférieur; et A représente un alkylène inférieur; à condition que, lorsque R3 représente un alkylpyrrolidinyle inférieur, alors R10 représente hydrogène; ou à un sel pharmaceutiquement acceptable d'un tel composé, utilisable comme agent anti-microbien.
• CN115490664
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of 20-deethylsilicine from a second-generation 2-cyano-.DELTA.3-piperidine synthon
  作者：David S. Grierson、Jean Luc Bettiol、Ildiko Buck、Henri Philippe Husson、Mario Rubiralta、Anna Diez

  DOI：10.1021/jo00050a012

  日期：1992.11

  The Zn2+ ion mediated reaction of the 2-cyano-DELTA3-piperidine 9a (X = SO2C6H5) with the silyl enol ether of Na-methyl-2-acetylindole (24) led to formation of compounds 29a,b (70%) resulting from introduction of the acetylindole moiety at the exocyclic (C-7) carbon center and migration of the phenylsulfonyl group from C-7 to C-4. In contrast, reaction of 2-Cyano-DELTA3-piperidine 9b (X = CN) with 24 gave the desired C-4 acetylindole-substituted products 36a,b (1:1.3 mixture; 72% overall yield). Attempts to cyclize intermediates 36 to the tetracyclic enamine 27 were unsuccessful. Alternatively, the Zn2+-catalyzed reaction of synthons 9a and 9b with indole gave the C-7 indole-substituted aminonitriles 37a,b and 38, respectively. These intermediates were converted to DELTA2-piperidine 40 on reaction with sodium dimethyl malonate and AgBF4. Stereoselective hydrogenation of the enamine double bond in 40 furnished the required cis 3,4-disubstituted piperidine 41, which was cyclized under acidic conditions to the target molecule, 20-deethylsilicine (20).