methyl N-(2-hydroxyethylamino)crotonate | 79011-08-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl N-(2-hydroxyethylamino)crotonate
• 英文别名: methyl 3-(2-hydroxyethylamino)crotonate；methyl (E)-3-((2-hydroxyethyl)amino)but-2-enoate；methyl (E)-3-(2-hydroxyethylamino)but-2-enoate
• CAS: 79011-08-8
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: HQNHEEOUOOANLH-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl N-(2-hydroxyethylamino)crotonate 以 甲醇 为溶剂， 反应 24.0h， 生成 dimethyl 4-(3-chlorophenyl)-1-(2-acetoxyethyl)-1,4-dihydropyridin-3,5-dicarboxylate
  参考文献：
  名称：

  2,3,8,8a-Tetrahydro-7H-oxazolo[3,2-a]pyridine: A new heterocyclic system

  摘要：

  Compounds with the previously unreported skeleton of 2,3,8,8a-tetrahydro-7H-oxazolo [3,2-a]pyridine were prepared by reactions between alpha,beta-unsaturated ketones or aldehydes and N-hydroxyethylenamines of acetoacetate esters. Other compounds like 1,4-dihydropyridines, aminocyclohexene and cyclohexadiene derivatives were also formed as minor products.

  DOI：

  10.1016/s0040-4020(01)86577-7
• 作为产物：
  描述：

  C.I.酸性橙108 、 乙酰乙酸甲酯 反应 24.0h， 以98%的产率得到methyl N-(2-hydroxyethylamino)crotonate
  参考文献：
  名称：

  2,3,8,8a-Tetrahydro-7H-oxazolo[3,2-a]pyridine: A new heterocyclic system

  摘要：

  Compounds with the previously unreported skeleton of 2,3,8,8a-tetrahydro-7H-oxazolo [3,2-a]pyridine were prepared by reactions between alpha,beta-unsaturated ketones or aldehydes and N-hydroxyethylenamines of acetoacetate esters. Other compounds like 1,4-dihydropyridines, aminocyclohexene and cyclohexadiene derivatives were also formed as minor products.

  DOI：

  10.1016/s0040-4020(01)86577-7

文献信息

• Benzannulation and <i>N</i> ‐Annulation of β‐Ketoenamines for Synthesizing Aniline and Pyridine Derivatives Using DMSO as a Methine Source
  作者：Pallaba Ganjan Dalai、Niranjan Panda

  DOI：10.1002/adsc.202200886

  日期：2022.11.8

  N-annulation of β-ketoenamines by the in-situ generated methyl(methylene)sulfonium ion from the reaction of dimethyl sulfoxide (DMSO) and 1,2-dibromoethane (DBE) was achieved. The β-ketoenamines underwent N-annulation to pyridine derivatives, while the N-alkylated enamines were benzannulated to afford substituted anilines. The utility of the intermediate methyl(methylene)sulfonium ion was further extended for

  通过二甲基亚砜（DMSO）和1,2-二溴乙烷（DBE）的反应原位产生的甲基（亚甲基）锍离子实现了β-酮烯胺的苯环化和N-环化。β-酮烯胺经 N-环化生成吡啶衍生物，而N-烷基化烯胺经苯环化生成取代的苯胺。中间体甲基（亚甲基）锍离子的用途进一步扩展用于合成亚甲基桥联双-1,3-二羰基化合物。
• N-substituted pyrrolinones from enamines and α-dicarbonyls
  作者：Esther Caballero、Pilar Puebla、María Domercq、Manuel Medarde、Jose-L. López、Arturo San Feliciano

  DOI：10.1016/s0040-4020(01)85268-6

  日期：1994.1

  The reaction between N-substituted enamines and phenylglyoxal or glyoxal yielded Delta(2)-pyrrolin-5-ones in moderate to good yields. An uncommon pyrrolo [2,1-b]thiazole derivative was formed as a minor product when a N-(2-mercaptoethyl)enamine was used as the starting reagent. An explanation for the regiochemistry of the reaction is proposed.
• Yakimovich, S. I.; Nikolaev, V. N., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 976 - 977
  作者：Yakimovich, S. I.、Nikolaev, V. N.

  DOI：——

  日期：——
• YAKIMOVICH S. I.; NIKOLAEV V. N., ZH. ORGAN. XIMII, 1981, 17, HO 5, 1104-1105
  作者：YAKIMOVICH S. I.、 NIKOLAEV V. N.

  DOI：——

  日期：——