1-(pyrrolidin-2-ylidene)propan-2-one | 32357-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(pyrrolidin-2-ylidene)propan-2-one
• 英文别名: pyrrolidin-2-ylidene-propan-2-one；1-pyrrolidin-2-ylidenepropan-2-one
• CAS: 32357-58-7
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: MJPFXBSXYTVTNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(pyrrolidin-2-ylidene)propan-2-one 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.0h， 生成 4-acetyl-2-(4-methylphenyl)-1,1-diphenyl-2,5,6,7-tetrahydro-1H-pyrrolo[1,2-d][1,2,4,3λ4]triazaborine
  参考文献：
  名称：

  A new bicyclic oxazaborines with a bridged nitrogen atom, their thermic rearrangement and fluorescence properties

  摘要：

  Cyclic beta-enaminones bearing secondary amino group react with 4-substituted benzenediazonium tetraphenylborates in dichloromethane to form substituted bicyclic [1,3,2 lambda(4)] oxazaborines The oxazaborines rearrange, on heating to 200 degrees C in the absence of solvent or in DMF or DMSO, to isomeric 2H-[1,2,4,3 lambda(4)] triazaborines. Previously prepared [1,3,2 lambda(4)] oxazaborines derived from acyclic beta-enaminones bearing secondary amino group either did not undergo the rearrangement or with a lot of difficulties and with negligible yield. The fluorescence behaviour of the prepared triazaborines was observed. These compounds fluoresce in 2-methyltetrahydrofurane and in solid state under low temperatures. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2011.11.004
• 作为产物：
  描述：

  3-(2-pyrrolidinylidene)pentan-2,4-dione 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以79%的产率得到1-(pyrrolidin-2-ylidene)propan-2-one
  参考文献：
  名称：

  通过钯催化的极化杂环烯胺的分子内 C-N 交叉偶联合成 [1,2-a]-稠合三环二氢喹啉

  摘要：

  建立了 [1,2-a]-稠合三环二氢喹啉的简单方法。该方法的关键步骤是合适的卤化（溴和氯）环状烯氨基酮、烯氨基酯和具有各种环大小（从五元到七元）的烯氨基腈的分子内 Buchwald-Hartwig 胺化反应。最佳反应条件（钯源、碱、配体）取决于起始烯胺的环大小，三环产物的产率为 65-98%。用高氯酸处理产物得到相应的高氯酸喹啉鎓。

  DOI：

  10.3998/ark.5550190.p009.723

文献信息

• Reactions of N-Phosphorylated Aziridines with Dianions Derived from Ethyl Acetoacetate and 1,3-Diketones: New Route to Substituted Pyrrolines and Pyrrolidines
  作者：Krystyna Osowska-Pacewicka、Andrzej Zwierzak

  DOI：10.1080/00397919808005953

  日期：1998.4

  Abstract The nucleophilic ring-opening of N-(diethoxyphosphory)aziridines by the dianions derived from ethyl acetoacetate and 1,3-diketones has been studied. Acid-mediated cyclisation and dephosphorylation of the resulting products to a number of substituted pyrrolines and pyrrolidines has been also investigated.

  摘要 研究了乙酰乙酸乙酯和 1,3-二酮衍生的二价阴离子对 N-（二乙氧基磷酸）氮丙啶的亲核开环。还研究了酸介导的环化和去磷酸化生成的许多取代吡咯啉和吡咯烷的产物。
• 1,2-Pentamethylene-1,4-dihydropyridine derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US03951988A1

  公开（公告）日：1976-04-20

  1,4-Dihydropyridines bearing carbonyl functions in the 3- and 5-positions, being optionally substituted by lower alkyl in the 6-position, being substituted in the 4-position by lower alkyl, phenyl, substituted phenyl or a heterocyclic group, and being fused through the 1- and 2-positions to a five, six or seven membered cycloalkyl ring, one methylene group of which can be replaced by sulfur, oxygen imino or alkylimino, are antihypertensive agents and coronary vessel dilators. The compounds, of which 6-methyl-4-(3-nitrophenyl)-1,2-pentamethylene-1,4-dihydropyridine-3,5-dica rboxylic acid 3,5-diethyl ester is a representative embodiment, are prepared through condensation of an ylideneacetoacetic acid ester and a cyclic enamino carbonyl derivative.

  3-和5-位带有羰基功能的1,4-二氢吡啶，可在6位被低烷基取代，在4位被低烷基、苯基、取代苯基或杂环基取代，并通过1-和2-位与五、六或七元环烷基环融合，其中一个亚甲基可以被硫、氧、亚胺或烷基亚胺取代，是降压剂和冠状血管扩张剂。这些化合物，其中6-甲基-4-(3-硝基苯基)-1,2-戊亚甲基-1,4-二氢吡啶-3,5-二羧酸3,5-二乙酯是一个典型实施例，是通过酰乙酸酯和环烯酮羰基衍生物的缩合反应制备的。
• Tetrahydroimidazolo[1,2-a]pyridine derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US03935220A1

  公开（公告）日：1976-01-27

  1,4-Dihydropyridines bearing carbonyl functions in the 3- and 5-positions, being optionally substituted by lower alkyl in the 6-position, being substituted in the 4-position by lower alkyl, phenyl, substituted phenyl or a heterocyclic group, and being fused through the 1- and 2-positions to a five, six or seven membered cycloalkyl ring, one methylene group of which can be replaced by sulfur, oxygen imino or alkylimino, are antihypertensive agents and coronary vessel dilators. The compounds, of which 6-methyl-4-(3-nitrophenyl)-1,2-pentamethylene-1,4-dihydropyridine-3,5-dica rboxylic acid 3,5-diethyl ester is a representative embodiment, are prepared through condensation of an ylideneacetoacetic acid ester and a cyclic enamino carbonyl derivative.

  3-和5-位带有羰基功能的1,4-二氢吡啶，6-位可选择性地被低碳基取代，4-位被低碳基、苯基、取代苯基或杂环基所取代，并通过1-和2-位融合到五、六或七元环烷基环上，其中一个亚甲基可以被硫、氧、亚氨基或烷基亚氨基所取代，是抗高血压药和冠状血管扩张剂。这些化合物，其中6-甲基-4-(3-硝基苯基)-1,2-戊亚甲基-1,4-二氢吡啶-3,5-二羧酸3,5-二乙酯是一个代表性实施例，是通过酰乙酰酸酯和环状烯氨酮羰基衍生物的缩合制备的。
• Pentahydroqunolizine derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US03948923A1

  公开（公告）日：1976-04-06

  1,4-Dihydropyridines bearing carbonyl functions in the 3- and 5-positions, being optionally substituted by lower alkyl in the 6-position, being substituted in the 4-position by lower alkyl, phenyl, substituted phenyl or a heterocyclic group, and being fused through the 1- and 2-positions to a five, six or seven membered cycloalkyl ring, one methylene group of which can be replaced by sulfur, oxygen imino or alkylimino, are anti-hypertensive agents and coronary vessel dilators. The compounds, of which 6-methyl-4-(3-nitrophenyl)-1,2-pentamethylene-1,4-dihydropridine-3,5-dicar boxylic acid 3,5-diethyl ester is a representative embodiment, are prepared through condensation of an ylideneacetoacetic acid ester and a cyclic enamino carbonyl derivative.

  3-和5-位带有羰基功能的1,4-二氢吡啶，6-位可选择性地被低烷基取代，4-位被低烷基、苯基、取代苯基或杂环基取代，通过1-和2-位与五、六或七元环环烷基融合，其中一个亚甲基可以被硫、氧、亚胺或烷基亚胺取代，是降压剂和冠状血管扩张剂。这些化合物通过酰乙酸乙酯和环状烯氨酮羰基衍生物的缩合反应制备而成，其中6-甲基-4-(3-硝基苯基)-1,2-戊亚甲基-1,4-二氢吡啶-3,5-二羧酸二乙酯是一种代表性的实施例。
• Tetrahydroindolizine derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US03951994A1

  公开（公告）日：1976-04-20

  1,4-Dihydropyridines bearing carbonyl functions in the 3- and 5-positions, being optionally substituted by lower alkyl in the 6-position, being substituted in the 4-position by lower alkyl, phenyl, substituted phenyl or a heterocyclic group, and being fused through the 1- and 2-positions to a five, six or seven membered cycloalkyl ring, one methylene group of which can be replaced by sulfur, oxygen imino or alkylimino, are antihypertensive agents and coronary vessel dilators. The compounds, of which 6-methyl-4-(3-nitrophenyl)-1,2-pentamethylene-1,4-dihydropyridine-3,5-dica rboxylic acid 3,5-diethyl ester is a representative embodiment, are prepared through condensation of an ylideneacetoacetic acid ester and a cyclic enamino carbonyl derivative.

  3-和5-位带有羰基功能的1,4-二氢吡啶，可在6-位被低烷基取代，4-位被低烷基、苯基、取代苯基或杂环基取代，并通过1-和2-位融合到五、六或七元环环烷基环上，其中一个亚甲基可以被硫、氧、亚氨基或烷基亚氨基替换，是降压剂和冠状血管扩张剂。这些化合物的代表性实施例是6-甲基-4-(3-硝基苯基)-1,2-戊亚甲基-1,4-二氢吡啶-3,5-二羧酸3,5-二乙酯，通过酰乙酰乙酸酯和环状烯酰亚胺羰基衍生物的缩合制备。