2-[1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl]-malonic acid dimethyl ester | 324025-34-5

• 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: 2-[1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl]-malonic acid dimethyl ester
• 英文别名: methyl 2-methoxycarbonyl-3-(4-methoxyphenyl)-4-benzoylbutanoate；dimethyl 2-(1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl)malonate；dimethyl 2-[1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl]malonate；[1-(4-methoxy-phenyl)-3-oxo-3-phenyl-propyl]-malonic acid dimethyl ester；[α-(4-Methoxy-phenyl)-β-benzoyl-aethyl]-malonsaeuredimethylester；[1-(4-Methoxy-phenyl)-3-oxo-3-phenyl-propyl]-malonsaeure-dimethylester；Dimethyl 2-[1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl]propanedioate
• CAS: 324025-34-5
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: RCSNBZHPILTGNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙二酸二甲酯 、 4-甲氧基查耳酮 在 Mg-Al-O-t-Bu hydrotalcite 作用下， 以 甲醇 为溶剂， 反应 1.38h， 以95%的产率得到2-[1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl]-malonic acid dimethyl ester
  参考文献：
  名称：

  Mg-Al-O- t - Bu水滑石促进的催化碳键形成

  摘要：

  发现Mg-Al-O- t -Bu水滑石催化剂是一种有效的，对环境有吸引力的，对1,4迈克尔加成反应有选择性的固体碱催化剂。Mg–Al–O– t – Bu水滑石通过Knoevenagel缩合反应将相应的活化羧酸酯或腈与各种醛缩合，对于简单合成α，β-不饱和酯和腈也有效。这些反应在室温下以Mg–Al–O– t – Bu水滑石的存在速率比在其他任何催化剂存在下的速率更高。

  DOI：

  10.1016/s0040-4020(00)00906-6

文献信息

• Layered Double Hydroxides-Supported Diisopropylamide: Synthesis, Characterization and Application in Organic Reactions
  作者：M. Lakshmi Kantam、A. Ravindra、Ch. Venkat Reddy、B. Sreedhar、B. M. Choudary

  DOI：10.1002/adsc.200505266

  日期：2006.3

  The layered double hydroxides-supported diisopropylamide (LDH-DA) catalyst is found to be an efficient and selective solid base for aldol, Knoevenagel, Henry, Michael, transesterification and epoxidation reactions under liquid phase conditions. LDH-DA is synthesized by the interaction of lithium diisopropylamide with LDH-NO3 (as-synthesized) and calcined LDH-NO3. The LDH-DA (Mg/Al, 3/1) and their precursors

  发现层状双氢氧化物负载的二异丙基酰胺（LDH-DA）催化剂是在液相条件下用于醇醛，Knoevenagel，Henry，Michael，酯交换和环氧化反应的有效且选择性的固体碱。LDH-DA是通过二异丙基氨基锂与LDH-NO 3（合成后）和煅烧的LDH-NO 3相互作用而合成的。通过使用各种仪器技术，如FT-IR，TGA和DTA，粉末XRD，固态27 Al MAS NMR光谱，SEM和XPS（ESCA ），可以很好地表征LDH-DA（Mg / Al，3/1）及其前体）。
• Chiral Bisphosphazides as Dual Basic Enantioselective Catalysts
  作者：Hiroshi Naka、Nobuhiko Kanase、Masahiro Ueno、Yoshinori Kondo

  DOI：10.1002/chem.200800230

  日期：2008.6.9

  Chiral bisphosphazides complexed with lithium salts efficiently catalyze the direct enantioselective 1,4-addition of dialkyl malonates to acyclic enones. Spectroscopic studies on the stoichiometry of the bisphosphazide and lithium salt have indicated the formation of a 1:1 species as the active enantioselective catalyst. It is suggested that the catalyst generates a complex of the protonated phosphazide

  与锂盐络合的手性二磷叠氮化物可有效催化丙二酸二烷基酯向无环烯酮的直接对映选择性1,4-加成反应。对双磷叠氮化物和锂盐的化学计量的光谱研究表明，形成了1：1的物种作为活性对映选择性催化剂。建议该催化剂产生质子化的磷叠氮化物和手性亲核试剂作为关键中间体的复合物。磷腈部分似乎是有前途的立体和化学选择性催化转化的双重基本功能。
• Magnesium-Lanthanum Mixed Metal Oxide: a Strong Solid Base for the Michael Addition Reaction
  作者：Bhaskar Veldurthy、Jean Marc Clacens、François Figueras

  DOI：10.1002/adsc.200404371

  日期：2005.5

  Michael additions were achieved quantitatively at room temperature with a broad spectrum of acceptors and donors, using a magnesium-lanthanum mixed oxide, a strong solid base. The best solvent for the reaction is dimethylformamide, but good yields were also obtained using toluene as solvent. The results obtained with magnesium-lanthanum are comparable to those reported for super bases. The catalyst

  使用镁-镧混合氧化物（一种坚固的固体碱），在室温下使用多种受体和施主定量完成迈克尔的添加。该反应的最佳溶剂是二甲基甲酰胺，但使用甲苯作为溶剂也能获得良好的收率。用镁镧获得的结果可与超碱报道的结果相媲美。可以将催化剂从反应混合物中分离出来，并循环五次而不会损失活性，而无需其他处理。
• Preparation of new layered double hydroxides exchanged with diisopropylamide for c-c bond forming reaction
  申请人：Council of Scientific and Industrial Research

  公开号：EP1352687A1

  公开（公告）日：2003-10-15

  The present invention relates to design and preparation of LDH- diisopropylamide through simple exchange process for the first time and its use in catalytic amounts for preparing aldols / α,β-unsaturated nitriles / α,β-unsaturated esters / transesterified products / β-nitroalkanols / Michael adducts and epoxide, resulting in higher yields.

  本发明涉及首次通过简单的交换过程设计和制备 LDH-二异丙基酰胺，并将其用于催化制备醛醇/α,β-不饱和腈/α,β-不饱和酯/酯交换产物/β-硝基烷醇/迈克尔加合物和环氧化物，从而获得更高的产率。
• 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzed Michael reactions
  作者：Weiping Ye、Junye Xu、Chin-Tong Tan、Choon-Hong Tan

  DOI：10.1016/j.tetlet.2005.08.010

  日期：2005.10

  1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD), a bicyclic guanidine base, has been found to be an excellent catalyst for Michael and Michael-type reactions. A wide variety of Michael donors and acceptors can participate in these reactions using 10-20 mol% of TDB. These reactions are mild, fast, easy to perform, produce excellent yields and can occur in several solvents without the need for strictly anhydrous conditions. (c) 2005 Elsevier Ltd. All rights reserved.