diethyl 2-(1-(4-methoxyphenyl)-2-nitroethyl)malonate | 404911-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl 2-(1-(4-methoxyphenyl)-2-nitroethyl)malonate
• 英文别名: Diethyl 2-[1-(4-methoxyphenyl)-2-nitroethyl]propanedioate
• CAS: 404911-73-5
• 化学式: C₁₆H₂₁NO₇
• 分子量: 339.345
• InChiKey: LKFSAWLBGBANNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl 2-(1-(4-methoxyphenyl)-2-nitroethyl)malonate 在 三氟化硼乙醚 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 12.25h， 生成 diethyl 2-(2-(4-methoxyphenyl)-2-oxoethylidene)malonate
  参考文献：
  名称：

  Boron Trifluoride Mediated Ring-Opening Reactions of trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates. Synthesis of Aroylmethylidene Malonates as Potential Building Blocks for Heterocycles

  摘要：

  trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates, upon treatment with BF3 center dot OEt2, undergo ring-opening rearrangement and the Nef reaction to give aroylmethylidene malonates. The products are found to be potential precursors for heterocycles, such as imidazoles, quinoxalines, and benzo[1,4]thiazines.

  DOI：

  10.1021/jo402848v
• 作为产物：
  描述：

  4-甲氧基-β-硝基苯乙烯 、 丙二酸二乙酯 在 三乙烯二胺 作用下， 以 neat (no solvent) 为溶剂， 生成 diethyl 2-(1-(4-methoxyphenyl)-2-nitroethyl)malonate
  参考文献：
  名称：

  Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions

  摘要：

  不同支撑的双官能硫脲在磺酰基聚苯乙烯树脂上的催化活性已经在不同亲核试剂对反式-β-硝基苯乙烯衍生物的硝基迈克尔加成中进行了研究。催化剂的活性取决于将手性硫脲与聚合物连接的链长度。最佳结果是使用由(L)-缬氨酸和1,6-己二胺衍生的硫脲得到的。催化剂可以在仅2%的负载下使用，并在纯净条件下至少重复使用四个周期。球磨促进的加成也非常有效。

  DOI：

  10.3762/bjoc.12.61

文献信息

• Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea
  作者：Tomotaka Okino、Yasutaka Hoashi、Tomihiro Furukawa、Xuenong Xu、Yoshiji Takemoto

  DOI：10.1021/ja044370p

  日期：2005.1.1

  thiourea moiety and an amino group on a chiral scaffold. Among them, thiourea 1e bearing 3,5-bis(trifluoromethyl)benzene and dimethylamino groups was revealed to be highly efficient for the asymmetric Michael reaction of 1,3-dicarbonyl compounds to nitroolefins. Furthermore, we have developed a new synthetic route for (R)-(-)-baclofen and a chiral quaternary carbon center with high enantioselectivity by Michael

  我们在手性支架上合成了一类带有硫脲部分和氨基的新型双功能催化剂。其中，带有 3,5-双（三氟甲基）苯和二甲氨基的硫脲 1e 被证明对于 1,3-二羰基化合物到硝基烯烃的不对称迈克尔反应非常有效。此外，我们通过迈克尔反应开发了 (R)-(-)-巴氯芬和具有高对映选择性的手性季碳中心的新合成路线。在这些反应中，我们假设催化剂的硫脲部分和氨基分别活化硝基烯烃和 1,3-二羰基化合物，以提供具有高对映选择性和非对映选择性的迈克尔加合物。
• Immobilization of 1,5,7-triazabicyclo [4.4.0] dec-5-ene over mesoporous materials: An efficient catalyst for Michael-addition reactions under solvent-free condition
  作者：Pranjal Kalita、Rajiv Kumar

  DOI：10.1016/j.apcata.2011.03.010

  日期：2011.4

  Immobilization of 1,5,7-triazabicyclo [4.4.0] dec-5-ene (TBD, a bicylic guanidine base) over mesoporous material like SBA-15 has been found to be an excellent catalyst for Michael-addition of β-nitro styrene with malonate. The reactions were performed under solvent-free condition at 373 K for 9 h. A wide variety of Michael donors and acceptors were investigated. Among them, high yield of Michael product

  已发现将1,5,7-三氮杂双环[4.4.0]癸-5-烯（TBD，双环胍碱）固定在诸如SBA-15的中孔材料上，是迈克尔加成β-硝基的极佳催化剂苯乙烯与丙二酸酯。反应在无溶剂条件下于373 K下进行9 h。对迈克尔的各种供体和受体进行了调查。其中，对-氯-硝基苯乙烯与丙二酸二甲酯之间的反应获得了高产率的迈克尔产物。
• Efficient Stereoselective Synthesis of Nitrocyclopropanes by the Oxidative Cyclization of Michael Adducts of Nitroolefins with Activated Methylene Compounds
  作者：Renhua Fan、Yang Ye、Weixun Li、Lingfei Wang

  DOI：10.1002/adsc.200800452

  日期：2008.11.3

  An efficient oxidative cyclopropanation of the Michael adducts of nitroolefins with activated methylene compounds by the combination of iodobenzene diacetate and tetrabutylammonium iodide is reported. Highly functionalized nitrocyclopropanes are synthesized in moderate to good yields via the Michael addition and cyclopropanation with high diastereoselectivity and enantioselectivity under mild conditions

  据报道，通过二碘代苯二乙酸酯和碘化四丁铵的结合，硝基烯烃的迈克尔加成物与活化的亚甲基化合物的有效氧化环丙烷化反应。在温和条件下，通过迈克尔加成和环丙烷化，以高非对映选择性和对映选择性，以中等至良好的产率合成了高度官能化的硝基环丙烷。
• Iodobenzene-Catalyzed Oxidative Cyclization for the Synthesis of Highly Functionalized Cyclopropanes
  作者：Yang Li、Hao Guo、Renhua Fan

  DOI：10.1055/s-0039-1690809

  日期：2020.3

  iodobenzene-catalyzed oxidative cyclization of Michael adducts of activated methylene compounds with nitroolefins or chalcones is developed. mCPBA is used as oxidant together with Bu4NI for the generation of a highly reactive iodine(III) species to mediate the cyclopropanation via a ligand exchange and reductive elimination process. A range of highly functionalized cyclopropanes are synthesized with

  开发了碘代苯催化的活化亚甲基化合物的迈克尔加合物与硝基烯烃或查耳酮的氧化环化反应。m CPBA与Bu 4 NI一起用作氧化剂，用于生成高反应性碘（III）物种，以通过配体交换和还原消除过程介导环丙烷化。合成具有高非对映选择性的一系列高度官能化的环丙烷。
• Mechanosynthesis of γ-nitro dicarbonyl compounds via CaCl2-catalyzed Michael addition
  作者：Chunman Jia、Da Chen、Chunyan Zhang、Qi Zhang、Bennan Cao、Zhendong Zhao

  DOI：10.1016/j.tet.2013.06.089

  日期：2013.9

  An efficient strategy for the mechanosynthesis of gamma-nitro dicarbonyl esters has been developed. A CaCl2-catalyzed Michael reaction, conducted at room temperature, afforded nitroalkenes from malonates in a short reaction time and in high yields. In most cases, polymerized side-reactions are eliminated or minimized. (C) 2013 Elsevier Ltd. All rights reserved.