1-methyl-3,5-bis(methyloxycarbonyl)pyridinium iodide | 54732-80-8

• 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
• 英文名称: 1-methyl-3,5-bis(methyloxycarbonyl)pyridinium iodide
• 英文别名: 3,5-dimethoxycarbonyl-1-methylpyridinium iodide；3,5-bis(methoxycarbonyl)-1-methylpyridin-1-ium iodide；3,5-Bis(methoxycarbonyl)-1-methylpyridin-1-ium iodide；dimethyl 1-methylpyridin-1-ium-3,5-dicarboxylate;iodide
• CAS: 54732-80-8
• 化学式: C₁₀H₁₂NO₄*I
• 分子量: 337.114
• InChiKey: XHGHQETZOSWGPE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.91
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl-3,5-bis(methyloxycarbonyl)pyridinium iodide 在 10-methyl-acridine 作用下， 以 水 、 异丙醇 为溶剂， 生成 1,4-dihydro-3,5-dimethoxycarbonyl-1-methylpyridine
  参考文献：
  名称：

  Marcus .lambda 的结构敏感性。用于 NAD+ 类似物之间的氢化物转移

  摘要：

  Constantes de vitesse et d'equilibre du transfert d'hydrure entre divers pyridinium, quinoleinium, acridinium et phenanthridinium

  DOI：

  10.1021/ja00210a036
• 作为产物：
  描述：

  3,5-吡啶二甲酸 在 硫酸 作用下， 以 丙酮 为溶剂， 生成 1-methyl-3,5-bis(methyloxycarbonyl)pyridinium iodide
  参考文献：
  名称：

  用于基因传递的新型可生物降解吡啶两亲物

  摘要：

  可生物降解的合成阳离子吡啶基两亲物 (SAINT) 被证明是有前途的非病毒载体系统，用于将 DNA 递送到真核细胞中。以 3,5-吡啶二羧酸为起始材料合成了六种新型 SAINT，两个酯基团作为阳离子头部基团和疏水尾部之间的连接体。通过差示扫描量热法和透射电子显微镜研究了两亲物的囊泡形成特性，而通过核磁共振光谱研究了二酯在水中的水解。最后，在培养的 COS-7 和 HepG-2 细胞上测定转染潜力和细胞毒性。((C) Wiley-VCH Verlag GmbH & Co. KGaA, 2003)。

  DOI：

  10.1002/ejoc.200300361

文献信息

• Novel Biodegradable Pyridinium Amphiphiles for Gene Delivery
  作者：Dirk Pijper、Erna Bulten、Jarmila Šmisterová、Anno Wagenaar、Dick Hoekstra、Jan B. F. N. Engberts、Ron Hulst

  DOI：10.1002/ejoc.200300361

  日期：2003.11

  Biodegradable synthetic cationic pyridinium-based amphiphiles (SAINTs) prove to be promising non-viral carrier systems for delivery of DNA into eukaryotic cells. Six novel SAINTs were synthesised from 3,5-pyridinedicarboxylic acid as starting material, with two ester groups as linkers between the cationic headgroup and the hydrophobic tails. The vesicle-forming properties of the amphiphiles were studied

  可生物降解的合成阳离子吡啶基两亲物 (SAINT) 被证明是有前途的非病毒载体系统，用于将 DNA 递送到真核细胞中。以 3,5-吡啶二羧酸为起始材料合成了六种新型 SAINT，两个酯基团作为阳离子头部基团和疏水尾部之间的连接体。通过差示扫描量热法和透射电子显微镜研究了两亲物的囊泡形成特性，而通过核磁共振光谱研究了二酯在水中的水解。最后，在培养的 COS-7 和 HepG-2 细胞上测定转染潜力和细胞毒性。((C) Wiley-VCH Verlag GmbH & Co. KGaA, 2003)。
• Productive trapping of NAD-type radicals. Non-biomimetic reduction of pyridinium saltsElectronic supplementary information (ESI) available: experimental procedure and characterization data. See: http://www.rsc.org/suppdata/cc/b2/b201813f/
  作者：Rodolfo Lavilla、M. Carmen Bernabeu、Enric Brillas、Inés Carranco、José Luis Díaz、Nereida Llorente、Marta Rayo、Alessandro Spada

  DOI：10.1039/b201813f

  日期：2002.4.11

  One-electron reduction of pyridinium salts (NAD+ analogues) generates dihydropyridyl radicals which may then be engaged in radical addition processes to regioselectively form gamma-substituted dihydropyridines.

  吡啶鎓盐（NAD +类似物）的单电子还原生成二氢吡啶基，然后可将其用于自由基加成过程中，以区域选择性地形成γ-取代的二氢吡啶。
• Regioselective Synthesis of Indolyldihydropyridines. A Remarkable Solvent Effect
  作者：Rodolfo Lavilla、Teresa Gotsens、Joan Bosch

  DOI：10.1055/s-1991-26587

  日期：——

  The synthesis of 1,2-dihydro-2-(3-indolyl)-1-methylpyridines and 1,4-dihydro-4-(3-indolyl)-1-methylpyridines through the addition of indoles to pyridinium salts in various solvents is described. Selective preparation of 1,2-dihydropyridines is possible performing the reaction in methanol as the solvent, whereas the 1,4-isomers are preferentially formed in dimethyl sulfoxide.

  介绍了在不同溶剂中通过吲哚与吡啶鎓盐的加成反应合成 1,2-二氢-2-(3-吲哚基)-1-甲基吡啶和 1,4-二氢-4-(3-吲哚基)-1-甲基吡啶的方法。 以甲醇为溶剂进行反应可以选择性地制备 1,2-二氢吡啶，而 1,4-异构体则优先在二甲亚砜中生成。
• Synthesis of Pyridine Acrylates and Acrylamides and Their Corresponding Pyridinium Ions as Versatile Cross-Linkers for Tunable Hydrogels
  作者：Günter Tovar、Heike Boehm、Sabine Laschat、Markus Mateescu、Isabell Nuss、Alexander Southan、Hayley Messenger、Seraphine Wegner、Julia Kupka、Monika Bach

  DOI：10.1055/s-0033-1338614

  日期：——

  A small library of cross-linkers for hydrogels was synthesized. The cross-linkers consisted of 2,6- and 3,5-diacylpyridine or 2,4,6-triacylpyridine as the core unit, which were tethered via ethylene glycol, amino ethanol, and 1,n-diamine spacers to terminal acrylate or acrylamide moieties. Esterification and amide formation of the terminal acryl units were found to be dependent on the ratio of NH/O in the spacer, the constitution pattern of the pyridine ring, and the total number of acryl groups. Thus, esters generally gave higher yields than amides decreasing with increasing number of NH in the spacer and with increasing number of acryl units. In the case of 3,5-diacylpyridine derivatives, these trends were less prominent as compared to the 2,6-diacylpyridine series, indicating that steric hindrance and unfavorable hydrogen bonding interaction of the spacers might influence the observed reactivity differences. The 3,5-diacylpyridines were converted to the N-methylpyridinium salts and selected members of both neutral and cationic 3,5-diacylpyridinium derivatives were submitted to hydrogelations with synthetic polymer poly(1-glycidylpiperazine) via aza-Michael addition and thiolated natural hyaluronan via thio-Michael reaction, respectively. Rheological properties of the resulting hydrogels were studied, revealing that both spacer type as well as charge affected elastic moduli and degree of swelling.
• Azole additions upon azinium salts
  作者：Rodolfo Lavilla、Teresa Gotsens、Marta Guerrero、Carme Masdeu、M.Carmen Santano、Cristina Minguillón、Joan Bosch

  DOI：10.1016/s0040-4020(97)00906-x

  日期：1997.10

  The additions of pyrrole and indole upon N-acetyl- and N-alkylpyridinium, quinolinium or isoquinolinium salts are reported. The resulting dihydroazines are either isolated or oxidised to the more stable aromatic compounds. The use of a two-phase system was studied and slight enantiomeric excesses were observed when chiral catalysts were used. The separation of enantiomers of some 4-indolyl-1,4-dihydropyridines was achieved by HPLC using chiral stationary phases. (C) 1997 Elsevier Science Ltd.