2-oxo-3-(pyrrolidin-1-ylcarbonyl)propylidenetiphenylphosphorane | 84981-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-oxo-3-(pyrrolidin-1-ylcarbonyl)propylidenetiphenylphosphorane
• 英文别名: 4-(triphenylphosphanylidene)-1-pyrrolidin-1-yl-butane-1,3-dione；4-(triphenylphosphoranylidene)acetoacetic acid pyrrolidide；1-Pyrrolidin-1-yl-4-(triphenyl-lambda5-phosphanylidene)butane-1,3-dione；1-pyrrolidin-1-yl-4-(triphenyl-λ5-phosphanylidene)butane-1,3-dione
• CAS: 84981-55-5
• 化学式: C₂₆H₂₆NO₂P
• 分子量: 415.472
• InChiKey: ZATWHYCJSGLKNH-UHFFFAOYSA-N

物化性质

• 沸点：
  616.2±57.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  色酮-3-甲醛 、 2-oxo-3-(pyrrolidin-1-ylcarbonyl)propylidenetiphenylphosphorane 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以54%的产率得到[2-hydroxy-5-(2-hydroxybenzoyl)phenyl]pyrrolidin-1-yl-methanone
  参考文献：
  名称：

  ‘Michael-Michael-Wittig’ Reactions of (2,4-Dioxobutylidene)phosphoranes with 3-Formylchromones

  摘要：

  4-(2′-羟基苯甲酰基)水杨酸酯和酰胺是通过(2,4-二氧代丁烯)三苯基膦与3-甲酰基香豆素的多米诺“迈克尔-反迈克尔-威蒂格”反应制备的。

  DOI：

  10.1055/s-2003-37104
• 作为产物：
  描述：

  四氢吡咯 、 2-氧-4-(三苯基膦)丁酸乙酯 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以79%的产率得到2-oxo-3-(pyrrolidin-1-ylcarbonyl)propylidenetiphenylphosphorane
  参考文献：
  名称：

  One-pot reactions of 2,4-(dioxobutylidene)phosphoranes. Efficient synthesis of 4-(2-hydroxybenzoyl)salicylic acid derivatives and buta-1,3-diene-1,4-dicarboxylates

  摘要：

  4-(2-Hydroxybenzoyl)salicylic esters and amides were prepared by domino 'Michael-Retro-Michael-Wittig' reactions of (2,4-dioxobutylidene)triphenylphosphoranes with 3-formylchromones.

  DOI：

  10.1016/j.tet.2007.02.062

文献信息

• Synthesis of 2-Alkenyl-3-alkoxycarbonylfurans by ‘Feist-Benary-Cyclo­condensation’ of (2,4-Dioxobutylidene)phosphoranes with Chloro­acetaldehyde and Subsequent Wittig Reactions
  作者：Peter Langer、Edith Holtz

  DOI：10.1055/s-2004-829560

  日期：——

  Functionalized furans were prepared by 'Feist-Benary-cyclocondensation' of (2,4-dioxobutylidene)phosphoranes with chloroacetaldehyde and subsequent Wittig reactions.

  通过（2,4-二氧代丁叉基）正膦与氯乙醛的“Feist-Benary-cyclocondensation”和随后的Wittig反应制备功能化呋喃。
• Synthesis of γ-(2,4-Dioxobut-1-ylidene)butenolides by Reaction of Masked 1,3-Dicarbonyl Dianions with Maleic Anhydrides and Phthaloyl Dichloride
  作者：Peter Langer、Uwe Albrecht、Van Thi Nguyen

  DOI：10.1055/s-2006-926383

  日期：——

  γ-(2,4-Dioxobut-1-ylidene)butenolides were prepared with very good regioselectivity by reaction of (2,4-dioxobutylidene)triphenylphosphoranes with maleic anhydrides. The reaction of 1,3-bis-silyl enol ethers with phthaloyl dichloride afforded benzo-annulated γ-(2,4-dioxobut-1-ylidene)butenolides; the formation of these products can be explained by formation of iso-phthaloyl dichloride and attack of the bis-silyl enol ether onto the latter.

  (2,4-二氧代丁-1-亚基)丁烯内酯是通过(2,4-二氧代丁-1-亚基)三苯基膦与马来酸酐反应制备的，具有非常好的区域选择性。1,3-双硅烷烯醇醚与邻苯二甲酰二氯化物的反应生成了苯annulated δ³-(2,4-二氧代丁-1-亚基)丁烯内酯；这些产物的形成可解释为异邻苯二甲酰二氯化物的形成和双硅烷烯醇醚对后者的攻击。
• Synthesis of 2-Alkenyl-3-(alkoxycarbonyl)furans Based on Feist−Benary Cyclocondensation of (2,4-Dioxobutylidene)phosphoranes with α-Haloketones and α-Chloracetaldehyde
  作者：Gerson Mross、Edith Holtz、Peter Langer

  DOI：10.1021/jo061153t

  日期：2006.10.1

  3-Acyl-2-alkenylfurans were prepared by "Feist-Benary cyclocondensation" of (2,4-dioxobutylidene) phosphoranes with chloracetaldehyde and alpha-haloketones and subsequent Wittig reactions.
• Karagiri, Nobuya; Takashima, Kenichi; Haneda, Toru, Journal of the Chemical Society. Perkin transactions I, 1984, # 3, p. 553 - 560
  作者：Karagiri, Nobuya、Takashima, Kenichi、Haneda, Toru、Kato, Tetsuzo

  DOI：——

  日期：——