1-ethoxycarbonylmethyl-3,5-dimethylpyridinium bromide | 64995-40-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-ethoxycarbonylmethyl-3,5-dimethylpyridinium bromide
• 英文别名: 1-(2-ethoxy-2-oxoethyl)-3,5-dimethylpyridin-1-ium bromide；Ethyl 2-(3,5-dimethylpyridin-1-ium-1-yl)acetate;bromide
• CAS: 64995-40-0
• 化学式: Br*C₁₁H₁₆NO₂
• 分子量: 274.158
• InChiKey: QOFFVEYZCPTOMU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.84
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-ethoxycarbonylmethyl-3,5-dimethylpyridinium bromide 在 palladium on activated charcoal sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 58.0h， 生成 5,7-Dimethyl-3-methylsulfanyl-pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid
  参考文献：
  名称：

  Tominaga, Yoshinori; Shiroshita, Yoshihide; Kurokawa, Tomohiko, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 477 - 487

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲基吡啶 、 溴乙酸乙酯 以 氘代二甲亚砜 为溶剂， 反应 8.0h， 以100%的产率得到1-ethoxycarbonylmethyl-3,5-dimethylpyridinium bromide
  参考文献：
  名称：

  Synthesis of Pyridine Acrylates and Acrylamides and Their Corresponding Pyridinium Ions as Versatile Cross-Linkers for Tunable Hydrogels

  摘要：

  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.

  DOI：

  10.1055/s-0033-1338614

文献信息

• Synthesis of Indolizines from Pyridinium Salts and Ethyl Bromodifluoroacetate
  作者：Xiaoya Hou、Sen Zhou、Yuli Li、Minjie Guo、Wentao Zhao、Xiangyang Tang、Guangwei Wang

  DOI：10.1021/acs.orglett.0c03540

  日期：2020.12.4

  Here we present a novel annulation of pyridinium salts with BrCF2CO2Et to access the indolizine derivatives with high efficiency. The α substitution of pyridine plays a key role in determining the reaction pathways. Various types of indolizines can be conveniently accessed from easily available pyridinium salts under mild and simple reaction conditions.

  在这里，我们提出了一种新型的吡啶盐与BrCF 2 CO 2 Et的环化方法，以高效地获得吲哚嗪衍生物。吡啶的α取代在确定反应途径中起关键作用。在温和而简单的反应条件下，可以从容易获得的吡啶鎓盐中方便地获得各种类型的吲哚嗪。
• 2-Phosphaindolizines via 1,5-electrocyclization
  作者：Raj K. Bansal、Anushka Surana、Neelima Gupta

  DOI：10.1016/s0040-4039(98)02645-8

  日期：1999.2

  N-Pyridinium dichlorophosphinomethylides disproportionate to generate bis(N-pyridinium ylidyl)phosphenium chloride which undergoes 1,5-electrocyclization to give 2-phosphaindolizines. In one-pot synthesis N-(alkoxycarbonylmethyl)pyridinium bromide reacts with PCl3 in presence of Et3N to form 2-phosphaindolizine.

  N-吡啶二氯膦基甲基化物不成比例生成氯化双（N-吡啶基吡啶基）phosph，将其进行1,5-电环化生成2-膦基吲哚酮。在一锅法合成中，N-（烷氧基羰基甲基）吡啶鎓溴化物在Et 3 N存在下与PCl 3反应形成2-磷酸吲哚嗪。
• Nitoroolefins. I. A New and Convenient Access to Indolizines and Pyrazolo[1,5-a]pyridines Using 1-Nitro-2-(phenylthio)ethylene
  作者：Yoshinori Tominaga、Yuichi Ichihara、Akira Hosomi

  DOI：10.3987/com-88-4682

  日期：——
• Tominaga, Yoshinori; Hosomi, Akira, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1449 - 1454
  作者：Tominaga, Yoshinori、Hosomi, Akira

  DOI：——

  日期：——
• Tominaga, Yoshinori; Ueda, Hiroshi; Ogata, Koichiro, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 1, p. 209 - 214
  作者：Tominaga, Yoshinori、Ueda, Hiroshi、Ogata, Koichiro、Kohra, Shinya

  DOI：——

  日期：——