cyano-2 oxo-5 diphenyl-3,5 pentanoate de methyle | 95276-54-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: cyano-2 oxo-5 diphenyl-3,5 pentanoate de methyle
• 英文别名: 2-cyano-5-oxo-3,5-diphenyl-valeric acid methyl ester；2-Cyan-5-oxo-3,5-diphenyl-valeriansaeure-methylester；β-Phenyl-γ-benzoyl-α-cyan-buttersaeure-methylester；2-Phenyl-3-benzoyl-propan-dicarbonsaeure-(1,1)-methylester-nitril；3,5-Diphenyl-2-cyan-5-oxo-valeriansaeure-methylester；Methyl 2-cyano-5-oxo-3,5-diphenylpentanoate
• CAS: 95276-54-3；112697-96-8；112697-98-0
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: JYAOGVKCVWJMBR-UHFFFAOYSA-N

物化性质

• 熔点：
  76 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  501.8±50.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyano-2 oxo-5 diphenyl-3,5 pentanoate de methyle 在 氢氧化钾 作用下， 生成 2-cyano-5-oxo-2-(3-oxo-1,3-diphenyl-propyl)-3,5-diphenyl-valeric acid methyl ester
  参考文献：
  名称：

  Kohler, Graustein, Merrill, Journal of the American Chemical Society, 1922, vol. 44, p. 2542

  摘要：

  DOI：
• 作为产物：
  描述：

  反式-查耳酮 、 氰乙酸甲酯 在 natural phosphate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到cyano-2 oxo-5 diphenyl-3,5 pentanoate de methyle
  参考文献：
  名称：

  硝酸锂改性的天然磷酸盐：构建碳-碳、碳-硫和碳-氮键的新型高效催化剂

  摘要：

  在天然磷酸盐中加入少量硝酸锂，然后煅烧，得到新的催化剂 Li/NP（重量比 LiNO3/NP = 1/15）。这种材料在胺、硫醇和活性亚甲基化合物与查耳酮衍生物的迈克尔加成反应中表现出催化活性，在温和的反应条件下具有高产率。Li/NP 用作催化剂，可在非均相条件下轻松合成 β-氨基酸、β-硫酸和 4 H-色烯。用这种方法没有观察到迈克尔缩合反应中常见的不希望有的副产物，例如 1,2-加成、双加成和聚合化合物。通过使用 Li/NP 进行简单过滤，简化了后处理程序。

  DOI：

  10.1080/10426500601160397

文献信息

• Construction of 1,2,5-Tricarbonyl Compounds using Methyl Cyanoacetate as a Glyoxylate Anion Synthon Combined with Copper(I) Iodide-Catalyzed Aerobic Oxidation
  作者：Se Hee Kim、Ko Hoon Kim、Jae Nyoung Kim

  DOI：10.1002/adsc.201100431

  日期：2011.12

  A practical and efficient synthesis of various 1,2,5-tricarbonyl compounds is described. The synthesis has been carried out by a conjugate addition of methyl cyanoacetate to the β-position of α,β-unsaturated carbonyl compounds and a subsequent copper(I) iodide-catalyzed aerobic oxidation. In addition, various α-aryl- and α-alkyl-α-keto esters have been synthesized using a similar approach.

  描述了一种实用而有效的合成各种1,2,5-三羰基化合物的方法。合成是通过将氰基乙酸甲酯共轭加到α，β-不饱和羰基化合物的β-位上进行的，然后进行碘化铜（I）催化的需氧氧化。另外，已经使用类似的方法合成了各种α-芳基-和α-烷基-α-酮酯。
• Facile Regiocontrolled Three-Step Synthesis of Poly-Substituted Furans, Pyrroles, and Thiophenes: Consecutive Michael Addition of Methyl Cyanoacetate to α,β-Enone, CuI-Mediated Aerobic Oxidation, and Acid-Catalyzed Paal-Knorr Synthesis
  作者：Se-Hee Kim、Jin-Woo Lim、Cheol-Hee Lim、Jae-Nyoung Kim

  DOI：10.5012/bkcs.2012.33.2.620

  日期：2012.2.20

  December 19, 2011An efficient synthesis of poly-substituted furans, pyrroles, and thiophenes was carried out in a regiocontrolledmanner via a three-step process; (i) conjugate addition of methyl cyanoacetate derivatives to α,β-enones, (ii)CuI-mediated aerobic oxidation, and (iii) Paal-Knorr type synthesis of five-membered heterocycles. Key Words : Furans, Pyrroles, Thiophenes, CuI, Paal-Knorr synthesisIntroductionRecently

  E-mail: [e-mail] 2011年12月6日接收，2011年12月19日接受 (i) 氰基乙酸甲酯衍生物与 α,β-烯酮的共轭加成，(ii) CuI 介导的有氧氧化，和 (iii) 五元杂环的 Paal-Knorr 型合成。关键词：呋喃，吡咯，噻吩，CuI，Paal-Knorr 合成介绍最近，我们报道了通过氰基乙酸甲酯与α,β-不饱和酮的共轭加成和随后的 CuI 介导的需氧氧化合成 2,5-二酮酯的有效方法。
• Unexpected Iodine-Promoted Aerobic Oxidation of α-Cyano-δ-keto Esters: A Facile Synthesis of α,δ-Dicarbonyl Esters
  作者：Ze Zhang、Hui Xu、Ming-Yue Weng、Hong Chen

  DOI：10.1055/s-0040-1707996

  日期：2020.6

  An efficient and green method for the synthesis of various α,δ-dicarbonyl esters has been developed via a conjugate addition of ethyl cyanoacetates to chalcones and subsequent iodine-promoted aerobic oxidation. The present protocol features mild reaction conditions, high efficiency, easily available starting materials, and broad substrate scope.

  通过将氰基乙酸乙酯共轭添加至查耳酮并随后进行碘促进的好氧氧化，已开发出一种高效且绿色的合成各种α，δ-二羰基酯的方法。本协议的特点是反应条件温和，高效，原料易得，底物范围广。
• Michael Additions of Methylene Active Compounds to Chalcone in Ionic Liquids without any Catalyst: The Peculiar Properties of Ionic Liquids
  作者：Mária Mečiarová、Štefan Toma

  DOI：10.1002/chem.200600870

  日期：2007.1.22

  Michael additions of malonodinitrile as well as several other reagents to chalcone have been found to proceed well in pure ionic liquids, without the addition of any catalyst. The catalytic effect of the residual acidity caused by hydrolysis of ionic liquids anions was excluded because HCl in dichloromethane did not catalyse the Michael addition of malonodinitrile. Piperidine was tested as the catalyst

  已经发现，在不添加任何催化剂的情况下，在纯离子液体中对丙二醛的迈克尔加成反应以及查尔酮的其他几种试剂都可以很好地进行。排除了由离子液体阴离子水解引起的残留酸度的催化作用，因为二氯甲烷中的HCl不能催化丙二腈的迈克尔加成反应。测试了哌啶作为催化剂，发现在离子液体中它比在二氯甲烷中是更好的催化剂。因此，出现了以下问题：离子液体对CH酸的离解常数有什么影响？
• Natural Phosphate Doped with Potassium Fluoride:  Efficient Catalyst for the Construction of a Carbon−Carbon Bond
  作者：Mohamed Zahouily、Bouchaïb Bahlaouan、Mina Aadil、Ahmed Rayadh、Saïd Sebti

  DOI：10.1021/op034161+

  日期：2004.3.1

  Natural phosphate-doped catalyst was found to be an efficient, environmentally attractive, and selective solid base catalyst for 1,4-Michael addition. The products of undesirable side reactions resulting from 1,2-adddition, polymerization, and bis-addition are not observed. The workup procedure is simplified by simple filtration with the use of natural phosphate alone or doped with potassium fluoride. Potassium fluoride-doped natural phosphate is used as catalyst for a facile synthesis of 4H-chromene under heterogeneous conditions.