methyl 3-oxo-4-(triphenylphosphoranylidene)butanoate | 98815-59-9

• 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: methyl 3-oxo-4-(triphenylphosphoranylidene)butanoate
• 英文别名: Methyl 4-(triphenylphosphoranylidene)acetoacetate；methyl 3-oxo-4-(triphenyl-λ5-phosphanylidene)butanoate
• CAS: 98815-59-9
• 化学式: C₂₃H₂₁O₃P
• 分子量: 376.392
• InChiKey: ZXAIAXRMRNCCHC-UHFFFAOYSA-N

物化性质

• 沸点：
  533.9±52.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  methyl 3-oxo-4-(triphenylphosphoranylidene)butanoate 在 三乙烯二胺 、 sodium hydride 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 methyl 2-diazo-5-[(4-methoxyphenyl)amino]-3-oxo-5-phenylpentanoate
  参考文献：
  名称：

  Diazoacetoacetate Enones for the Synthesis of Diverse Natural Product-like Scaffolds

  摘要：

  Diazoacetoacetate enones are a new class of Michael acceptors that enable the efficient construction of natural product-like scaffolds. Through their Michael addition reactions, including those with silyl enol ethers, indoles, pyrroles, and amines, delta-functionalized diazoacetoacetates are formed in high yield and with overall operational efficiency. Subsequent catalytic dinitrogen extrusion reactions provide access to a diverse series of natural product-like carbo- and heterocyclic ring systems in only three steps from commercial materials.

  DOI：

  10.1021/ol4015199
• 作为产物：
  描述：

  4-氯乙酰乙酸甲酯 在 碳酸氢钠 作用下， 以 水 、 苯 为溶剂， 生成 methyl 3-oxo-4-(triphenylphosphoranylidene)butanoate
  参考文献：
  名称：

  重氮乙酰乙酸酯酮与未活化炔烃的热诱导分子内苯环合反应：取代的6H-苯并[c]二甲基苯的合成

  摘要：

  抽象的 已开发了一种简便有效的分子内苯环芳构化策略，用于由重氮乙酰乙酸酯烯酮与未活化的炔烃束缚合成取代的6 H-苯并[ c ]色烯。该反应在操作简单的条件下以中等至良好的收率进行，其中关键的步骤是热诱导中间体乙烯基烯酮的[4 + 2]环化。 已开发了一种简便有效的分子内苯环芳构化策略，用于由重氮乙酰乙酸酯烯酮与未活化的炔烃束缚合成取代的6 H-苯并[ c ]色烯。该反应在操作简单的条件下以中等至良好的收率进行，其中关键的步骤是热诱导中间体乙烯基烯酮的[4 + 2]环化。

  DOI：

  10.1055/s-0039-1690191

文献信息

• Domino Primary Alcohol Oxidation-Wittig Reaction: Total Synthesis of ABT-418 and (<i>E</i>)-4-Oxonon-2-enoic Acid
  作者：Santosh Tilve、Jyoti Shet、Vidya Desai

  DOI：10.1055/s-2004-829123

  日期：——

  Domino oxidation of primary alcohols to α,β-unsaturated compounds using the combination of PCC-NaOAc and stabilized Wittig reagent and its application towards total synthesis of ABT-418 and 4-oxonon-2-enoic acid is described.

  描述了使用 PCC-NaOAc 和稳定的 Wittig 试剂将伯醇多米诺氧化为 α,β-不饱和化合物及其在 ABT-418 和 4-oxonon-2-enoic 酸全合成中的应用。
• Regio- and Diastereoselective Synthesis of Functionalized Cyclopentenones by Domino Michael-Ester-Wittig Reactions of (3-Alkoxycarbonyl-2-oxopropylidene)triphenylphosphoranes with Maleic Diesters
  作者：Peter Langer、Bettina Kracke

  DOI：10.1055/s-2001-18085

  日期：——

  The domino Michael-Ester-Wittig reaction of maleic diesters with (3-alkoxycarbonyl-2-oxopropylidene)triphenylphosphoranes resulted in regio- and diastereoselective formation of functionalized cyclopentenones.

  马来酸二酯与(3-烷氧基羧基-2-氧代丙烯基)三苯基磷烷的多米诺迈克尔-埃斯特-维蒂希反应导致了功能化环戊烯酮的区域性和二消旋选择性形成。
• ‘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。