2-(1-(4-硝基苯基)-3-氧代-3-苯基丙基)丙二酸二乙酯 | 171860-01-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 中文名称: 2-(1-(4-硝基苯基)-3-氧代-3-苯基丙基)丙二酸二乙酯
• 英文名称: diethyl 2-(1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)malonate
• 英文别名: [1-(4-nitro-phenyl)-3-oxo-3-phenyl-propyl]-malonic acid diethyl ester；[1-(4-Nitro-phenyl)-3-oxo-3-phenyl-propyl]-malonsaeure-diaethylester；Diethyl 2-[1-(4-nitrophenyl)-3-oxo-3-phenylpropyl]propanedioate
• CAS: 171860-01-8
• 化学式: C₂₂H₂₃NO₇
• 分子量: 413.427
• InChiKey: AJJDNZVRVBFDGV-UHFFFAOYSA-N

物化性质

• 熔点：
  97.0-97.5 °C
• 沸点：
  554.6±50.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(1-(4-硝基苯基)-3-氧代-3-苯基丙基)丙二酸二乙酯 在 selenium(IV) oxide 、 sodium acetate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  SYNTHESIS AND SPECTRAL CHARACTERIZATION OF DIETHYL 2-[ARYL(4-ARYL-1,2,3-SELENADIAZOL-5-YL)METHYL]MALONATE

  摘要：

  Synthesis and characterization of several diethyl 2-[aryl(4-aryl-1,2,3-selenadiazol-5-yl)methyl]malonates are reported.

  DOI：

  10.1080/10426500490485255
• 作为产物：
  描述：

  乙酸对硝基亚苄基 在 sodium hydroxide 、 二乙胺 作用下， 生成 2-(1-(4-硝基苯基)-3-氧代-3-苯基丙基)丙二酸二乙酯
  参考文献：
  名称：

  197.查耳酮和相关化合物。第二部分 在查耳酮体系中添加硫醇和酯

  摘要：

  DOI：

  10.1039/jr9570001015

文献信息

• The Michael Addition of Active Methylene Compounds to Chalcone Derivatives using a Catalytic Amount of Iodine and K₂CO₃ at Room Temperature
  作者：Yi-Ming Ren、Chun Cai

  DOI：10.3184/174751911x12984726527461

  日期：2011.3

  A convenient method for the Michael addition of active methylene compounds to chalcone derivatives has been developed using the inexpensive and environmentally friendly reagent I2/K2CO3 at room temperature. The method is mild and proceeds with good to high yields.

  使用廉价且环保的试剂 I2/K2CO3 在室温下开发了一种方便的将活性亚甲基化合物迈克尔加成到查耳酮衍生物的方法。该方法温和且收率高。
• Phase-Transfer Catalyzed Michael Addition Reaction Using a New C2-Symmetric Quaternary Ammonium Salt Derived From l-Proline
  作者：Ce Su、Yi-Ming Xie、Qing-Tang Zhang

  DOI：10.1007/s10562-011-0595-1

  日期：2011.7

  A new C2-symmetric quaternary ammonium salt easily prepared from l-proline, was developed and used as an efficient phase-transfer catalyst (PTC) in Michael addition reaction of various active methylene compounds to aromatic enones. Malonate esters and acetylacetone were reacted smoothly with various α, β-unsaturated ketones in good to excellent yields, the reaction conditions were optimized and the

  开发了一种易于从 l-脯氨酸制备的新型 C2 对称季铵盐，并将其用作各种活性亚甲基化合物与芳香烯酮的迈克尔加成反应中的有效相转移催化剂 (PTC)。丙二酸酯和乙酰丙酮与各种α，β-不饱和酮以良好的收率顺利反应，优化了反应条件，并研究了底物范围。因此，在相转移催化条件下建立了一种实用的迈克尔加成方法，该方法具有催化剂易得、反应条件温和、反应时间短、后处理简单等优点。
• Highly Efficient Mechanochemical Reactions of 1,3-Dicarbonyl Compounds with Chalcones and Azachalcones Catalyzed by Potassium Carbonate
  作者：Guan-Wu Wang、Ze Zhang、Ya-Wei Dong、Koichi Komatsu

  DOI：10.1055/s-2003-43350

  日期：——

  Under the high-speed vibration milling conditions, K2CO3 was found to be a very efficient catalyst for the solvent-free Michael reactions of 1,3-dicarbonyl compounds with chalcones and azachalcones. In most cases, conventional side reactions were avoided and thus excellent yields were achieved. The influences of other catalysts and the vibration frequency on the Michael reaction were investigated.

  在高速振动研磨条件下，发现K2CO3是一种非常有效的催化剂，能够无溶剂地促进1,3-二酮化合物与查尔酮和阿扎查尔酮之间的迈克尔反应。在大多数情况下，避免了常规的副反应，从而实现了优异的产率。研究了其他催化剂和振动频率对迈克尔反应的影响。
• Base-Controlled Selective Conversion of Michael Adducts of Malonates with Enones in the Presence of Iodine
  作者：Chun-Bao Miao、Min Zhang、Zong-Yong Tian、Hai-Tao Xi、Xiao-Qiang Sun、Hai-Tao Yang

  DOI：10.1021/jo201879t

  日期：2011.12.2

  An efficient base-controlled selective conversion of the Michael adducts of malonates with enones in the presence of iodine is reported. Highly functionalized cyclopropane, oxetane, and α-hydroxylmalonate derivatives are obtained selectively using DBU, Na2CO3, and NaOAc as the base, respectively. O2 was identified to be crucial to the formation of oxetane and α-hydroxylmalonate derivatives.

  据报道在碘存在下，丙二酸酯的迈克尔加成物与烯酮的有效的碱控制的选择性转化。分别使用DBU，Na 2 CO 3和NaOAc作为碱分别选择性地获得高度官能化的环丙烷，氧杂环丁烷和α-羟基丙二酸酯衍生物。O 2被确定对于氧杂环丁烷和α-羟基丙二酸酯衍生物的形成至关重要。
• Solvent-Controlled Oxidative Cyclization for Divergent Synthesis of Highly Functionalized Oxetanes and Cyclopropanes
  作者：Yang Ye、Chen Zheng、Renhua Fan

  DOI：10.1021/ol9012102

  日期：2009.7.16

  An efficient solvent-controlled oxidative cyclization of Michael adducts of malonates with chalcones with the combination of iodosobenzene and tetrabutylammonium iodide is reported. Highly functionalized oxetanes and cyclopropanes were divergently synthesized in moderate to excellent yields with high diastereoselectivity.

  报道了碘代苯和碘化四丁基铵的组合物对丙二酸酯与查耳酮的迈克尔加合物的有效溶剂控制的氧化环化反应。高官能度的氧杂环丁烷和环丙烷以中等到极好的收率和高非对映选择性发散地合成。