1-methylethyl 3-oxo-4-(triphenylphosphoranylidene)butanoate

• 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: 1-methylethyl 3-oxo-4-(triphenylphosphoranylidene)butanoate
• 英文别名: 4-(triphenylphosphanylidene)acetic acid isopropyl ester；1-methylethyl 3-oxo-4-(phosphoranylidene)butanoate；isopropyl 4-(triphenylphosphinylidene)acetoacetate；Isopropyl 3-oxo-4-(triphenylphosphoranylidene)butanoate；Propan-2-yl 3-oxo-4-(triphenyl-lambda5-phosphanylidene)butanoate；propan-2-yl 3-oxo-4-(triphenyl-λ5-phosphanylidene)butanoate
• 化学式: C₂₅H₂₅O₃P
• 分子量: 404.445
• InChiKey: NZUNSGWFZUENNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methylethyl 3-oxo-4-(triphenylphosphoranylidene)butanoate 在 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 isopropyl (E)-2-(prop-enyl)furan-3-carboxylate
  参考文献：
  名称：

  Synthesis of 2-Alkenyl-3-(alkoxycarbonyl)furans Based on Feist−Benary Cyclocondensation of (2,4-Dioxobutylidene)phosphoranes with α-Haloketones and α-Chloracetaldehyde

  摘要：

  3-Acyl-2-alkenylfurans were prepared by "Feist-Benary cyclocondensation" of (2,4-dioxobutylidene) phosphoranes with chloracetaldehyde and alpha-haloketones and subsequent Wittig reactions.

  DOI：

  10.1021/jo061153t

文献信息

• Preparation of Some Novel, Highly Unstable Chain Conjugated 2<i>H</i>-Pyran-5-carboxylates
  作者：Cornelis M. Moorhoff

  DOI：10.1002/jccs.200300126

  日期：2003.8

  Aldol condensations of conjugated unsaturated β-ketoesters and unsaturated aldehydes gave chain conjugated 2H-pyran-5-carboxylates.

  共轭不饱和 β-酮酯和不饱和醛的醛醇缩合产生链共轭 2H-吡喃-5-羧酸盐。
• ‘Michael-Michael-Wittig’ Reactions of (2,4-Dioxobutylidene)phosphoranes with 3-Formylchromones
  作者：Peter Langer、Edith Holtz

  DOI：10.1055/s-2003-37104

  日期：——

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

  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。
• Synthesis of 4,5-Benzotropones by Cyclization of 1,3-Bis-Silyl Enol Ethers with 1,2-Dialdehydes
  作者：Uwe Albrecht、Thi Hong Van Nguyen、Peter Langer

  DOI：10.1021/jo049736v

  日期：2004.5.1

  The cyclization of 1,3-bis-silyl enol ethers or (2,4-dioxobutylidene)triphenylphosphoranes with phthalic dialdehyde allowed a convenient synthesis of a variety of 4,5-benzotropones. The hydrogenation of benzotropones afforded functionalized benzocycloheptanones which were transformed into tricyclic butenolides.

  1，3-双-甲硅烷基烯醇醚或（2,4-二氧代丁烯）三苯基膦与邻苯二甲酸二醛的环化反应可以方便地合成各种4,5-苯并丙酮。苯并二氢萘酮的氢化得到官能化的苯并环庚酮，其被转化为三环丁烯内酯。
• 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。
• Moorhoff, Cornelis M.; Schneider, David F.; Winkler, Dave, Journal of Chemical Research, Miniprint, 1998, # 12, p. 3461 - 3483
  作者：Moorhoff, Cornelis M.、Schneider, David F.、Winkler, Dave

  DOI：——

  日期：——