1-(2-ethoxy-2-oxoethyl)-2,6-dimethylpyridin-1-ium bromide | 31778-09-3

• 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-(2-ethoxy-2-oxoethyl)-2,6-dimethylpyridin-1-ium bromide
• 英文别名: ethyl 2-(2,6-dimethylpyridin-1-ium-1-yl)acetate;bromide
• CAS: 31778-09-3
• 化学式: Br*C₁₁H₁₆NO₂
• 分子量: 274.158
• InChiKey: KWCNCPHRAJDMCA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.84
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30.18
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(2-ethoxy-2-oxoethyl)-2,6-dimethylpyridin-1-ium bromide 在 甲醇 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 1.0h， 以92%的产率得到2,3-dihydro-5-methylindolizin-2-one
  参考文献：
  名称：

  重新讨论了chichibabin吲哚嗪的合成：通过溶剂化4-烷氧基羰基-3-氧代四氢喹啉鎓盐合成吲哚并酮。

  摘要：

  研究了4-烷氧基羰基-（或4-酰基）-3-氧代-1,2,3,4-四氢喹啉亚基（1-4）的溶剂分解，发现三种反应竞争地进行。因此，通过醇解作用，可以制得Chichibabin重排产物2，3-二氢-2-吲哚并酮（5-8），在三氟乙醇或甲醇水溶液中进行溶剂分解，导致开环（以及随后的酯裂解）为2-乙酸基氧羰基吡啶鎓10，参见图15和16，并且水解导致对1-烷氧基羰基甲基吡啶-2-丙酸酯11或13（随后至12或14）的开环。特征在于，与较小的烷氧羰基取代的那些反应相比，叔丁氧羰基取代的所有烷基化反应进行得明显更快。基于动力学测量结果，提出了包括乙烯酮中间体在内的溶剂分解的一般机理。

  DOI：

  10.1021/jo0011639
• 作为产物：
  描述：

  2,6-二甲基吡啶 、 溴乙酸乙酯 以 氘代二甲亚砜 为溶剂， 以20%的产率得到1-(2-ethoxy-2-oxoethyl)-2,6-dimethylpyridin-1-ium 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

• Preparation of New Nitrogen-Bridged Heterocycles. 5. Smooth Michael Additions of 2(3<i>H</i>)-Indolizinone Derivatives
  作者：Akikazu Kakehi、Suketaka Ito、Bunzo Wada、Kozo Watanabe、Kenji Nishimura、Aiichiro Kumagai

  DOI：10.1246/bcsj.55.3590

  日期：1982.11

  some 2(3H)-indolizinone derivatives to α,β-unsaturated nitriles, esters, and an amide gave the corresponding double Michael adducts, 3,3-disubstituted 2(3H)-indolizinones, in moderate to high yields, and those to methyl vinyl ketone afforded further condensed products, spiro[cyclohexane-1,3′(2′H)-indolizin]-2′-ones, instead of the expected 1:2 adducts. On the other hand, the reactions of the indolizinones

  一些 2(3H)-吲哚嗪酮衍生物与 α,β-不饱和腈、酯和酰胺的迈克尔加成得到相应的双迈克尔加合物，3,3-二取代的 2(3H)-吲哚嗪酮，产率中等至高，和那些与甲基乙烯基酮的反应提供了进一步的缩合产物，螺[环己烷-1,3'(2'H)-indolizin]-2'-酮，而不是预期的 1:2 加合物。另一方面，吲哚嗪酮与在 β 位具有适当离去基团的活化乙烯或炔酯的反应形成不稳定的 1:1 迈克尔加合物，其转化为稳定的 2-酰氧基-或 2-烷氧基-通过用一些酰化剂或烷化剂以相对较好的收率处理得到 3-乙烯基吲哚嗪衍生物。
• 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。
• Preparation of new nitrogen-bridged heterocycles. Synthesis and some reactions of 2,3-dihydroindolizin-2-one derivatives
  作者：Akikazu Kakehi、Suketaka Ito、Kozo Watanabe、Masahiko Kitagawa、Sadafumi Takeuchi、Toshio Hashimoto

  DOI：10.1021/jo01313a017

  日期：1980.12
• Ezquerra, J.; Alvarez-Builla, J., Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1151 - 1157
  作者：Ezquerra, J.、Alvarez-Builla, J.

  DOI：——

  日期：——
• KAKEHI AKIKAZU; ITO SUKETAKA; WATANABE KOZO; KITAGAWA MASAHIKO; TAKEUCHI +, J. ORG. CHEM., 1980, 45 NO 25, 5100-51004
  作者：KAKEHI AKIKAZU、 ITO SUKETAKA、 WATANABE KOZO、 KITAGAWA MASAHIKO、 TAKEUCHI +

  DOI：——

  日期：——