1-carbethoxymethyl-4-dimethylaminopyridinium bromide

• 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-carbethoxymethyl-4-dimethylaminopyridinium bromide
• 英文别名: N-carbethoxy-4-dimethylaminopyridinium bromide；1-ethoxycarbonylmethyl-4-dimethylaminopyridinium bromide；4-(dimethylamino)-1-(2-ethoxy-2-oxoethyl)pyridinium bromide；N-carbethoxymethyl-4-dimethylaminopyridinium bromide；ethyl 2-[4-(dimethylamino)pyridin-1-ium-1-yl]acetate;bromide
• 化学式: Br*C₁₁H₁₇N₂O₂
• 分子量: 289.172
• InChiKey: ISQVXVVZSIPRCB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.39
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-carbethoxymethyl-4-dimethylaminopyridinium bromide 在 氢溴酸 、 乙酸酐 、 三乙胺 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.25h， 生成 N-(5,6-dicarboxy-1H-indene-1,3(2H)-dion-2-yl)-4'-dimethylaminopyridinium betaine anhydride
  参考文献：
  名称：

  N-羧甲基吡啶鎓盐缩合反应中取代的邻苯二甲酸和酸酐的反应性研究及新型N-（1H-茚-1,3（2H）-dion-2-Yl）吡啶甜菜碱的合成

  摘要：

  DOI：

  10.1007/bf02251820
• 作为产物：
  描述：

  4-二甲氨基吡啶 、 溴乙酸乙酯 以 乙醚 为溶剂， 以96%的产率得到1-carbethoxymethyl-4-dimethylaminopyridinium bromide
  参考文献：
  名称：

  Sharma, Anupama; Gupta, Neelima; Bansal, Raj K., Journal of the Indian Chemical Society, 2013, vol. 90, # 4, p. 525 - 528

  摘要：

  DOI：

文献信息

• Rh(III)-Catalyzed Oxidative Annulation Leading to Substituted Indolizines by Cleavage of C(sp²)–H/C(sp³)–H Bonds
  作者：Bingxue Shen、Bin Li、Baiquan Wang

  DOI：10.1021/acs.orglett.6b01181

  日期：2016.6.17

  Rhodium(III)-catalyzed oxidative annulation reactions of pyridinium trifluoromethanesulfonate salts with alkynes leading to substituted indolizines by cleavage of C(sp2)–H/C(sp3)–H bonds are developed. The starting materials are readily available, and the reactions have a broad substrate scope. This reaction overcomes some drawbacks of the previous indolizine synthetic methods and provides a new efficient

  开发了铑（III）催化的三氟甲烷磺酸吡啶鎓盐与炔烃的氧化环化反应，通过裂解C（sp 2）-H / C（sp 3）-H键可生成取代的吲哚嗪。起始原料容易获得，并且反应具有广泛的底物范围。该反应克服了以前的吲哚嗪合成方法的一些缺点，并提供了一种新的有效途径来制备吲哚嗪衍生物。
• Sharma, Anupama; Gupta, Neelima; Bansal, Raj K., Journal of the Indian Chemical Society, 2013, vol. 90, # 4, p. 525 - 528
  作者：Sharma, Anupama、Gupta, Neelima、Bansal, Raj K.

  DOI：——

  日期：——
• [4 + 1 + 1] Annulations of α-Bromo Carbonyls and 1-Azadienes toward Fused Benzoazaheterocycles
  作者：Rong Zeng、Changyu Shan、Ming Liu、Kun Jiang、Ying Ye、Tian-Yu Liu、Ying-Chun Chen

  DOI：10.1021/acs.orglett.9b00598

  日期：2019.4.5

  An unexpected [4 + 1 + 1] annulation between alpha-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2H)-ones or 2-methylenebenzo[b]thiophene-3(2H)-ones, has been observed in the presence of DABCO and Cs2CO3. These reactions stand in contrast to the common [4 + 1] cyclization reactions of azadienes with the related sulfonium ylides. A range of fused benzofuro[3,2-b]pyridines and benzo[4,5]thieno[3,2-b]pyridines have been efficiently constructed in fair to excellent yields.
• Nallu; Sathiskumar; Sangeetha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 4, p. 295 - 298
  作者：Nallu、Sathiskumar、Sangeetha、Sarkunam

  DOI：——

  日期：——
• Synthesis of complex dispirocyclopentanebisoxindoles via cycloaddition reactions of 4-dimethylamino-1-alkoxycarbonylmethylpyridinium bromides with 2-oxoindolin-3-ylidene derivatives
  作者：Li-Juan Lu、Qin Fu、Jing Sun、Chao-Guo Yan

  DOI：10.1016/j.tet.2014.02.050

  日期：2014.4

  The cycloaddition reactions of 4-dimethylamino-1-alkoxycarbonylmethylpyridinium bromides with various 2-oxoindolin-3-ylidene derivatives in ethanol in the presence of triethylamine afforded the unprecedented dispirocyclopentanebisoxindole derivatives in good yields and in high diastereoselectivity. Under similar reaction conditions, the reactions of 1-alkoxycarbonylmethylpyridinium bromides with 3-phenacylideneoxindoles only resulted in 4-oxo-3-(2-oxoindolin-3-ylidene)-4-arylbutanoates. The stereochemistry of the complex spirooxindoles was established by H-1 NMR data and single crystal structures. (C) 2014 Elsevier Ltd. All rights reserved.