1-O-ethyl 8-O-methyl 3-nitrooct-2-enedioate | 1038619-07-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-O-ethyl 8-O-methyl 3-nitrooct-2-enedioate
• CAS: 1038619-07-6
• 化学式: C₁₁H₁₇NO₆
• 分子量: 259.259
• InChiKey: HDWOHDQBWRSHJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  95.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-环己基羟基胺盐酸盐 、 1-O-ethyl 8-O-methyl 3-nitrooct-2-enedioate 在 三乙胺 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 18.0h， 以73%的产率得到ethyl 3-amino-4-cyano-2-(5-methoxy-5-oxopentyl)-9H-fluorene-1-carboxylate
  参考文献：
  名称：

  β-Nitroacrylates as key starting materials for the one-pot synthesis of densely functionalized penta-substituted anilines

  摘要：

  The reaction of ylidene malononitriles with beta-nitroacrylates, in Et3N/MeCN, affords the one-pot synthesis of a new class of penta-substituted, densely functionalized anilines in satisfactory to good overall yields. The method represents a very important improvement of the recent strategy for the preparation of anilines from conjugated nitroalkenes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.065

文献信息

• Michael Reaction of Nitroalkanes with β-Nitroacrylates under a Solid Promoter: Advanced Regio- and Diastereoselective Synthesis of Nitro-Functionalized α,β-Unsaturated Esters and 1,3-Butadiene-2-carboxylates
  作者：Alessandro Palmieri、Serena Gabrielli、Roberto Ballini

  DOI：10.1002/adsc.201000142

  日期：——

  of nitro‐functionalized α,β‐unsaturated esters has been prepared by a regio‐ and diastereoselective Michael addition of nitroalkanes to β‐nitroacrylates, performed at room temperature, under carbonate on polymer as promoter, and in the presence of ethyl acetate as eco‐friendly solvent. Moreover, by the modular choice of the reaction conditions the method allows the synthesis of 1,3‐butadiene‐2‐carboxylates

  在室温下，在碳酸酯作为助催化剂的聚合物上，在室温下，通过将硝基烷烃进行区域和非对映选择性迈克尔加成到β-硝基丙烯酸酯中，制备了一类新型的硝基官能化的α，β-不饱和酯。作为环保溶剂。此外，通过模块化选择反应条件，该方法可以合成1,3-丁二烯-2-羧酸盐。
• A new fully heterogeneous synthesis of pyrrole-2-acetic acid derivatives
  作者：Serena Gabrielli、Ludovica Ciabattoni、Susanna Sampaolesi、Roberto Ballini、Alessandro Palmieri

  DOI：10.1039/c6ra05348c

  日期：——

  Herein, we present a new general and efficient protocol to synthesize pyrrole-2-acetic acid derivatives starting from pyrroles and β-nitroacrylates, under fully heterogeneous conditions.

  在本文中，我们提出了一种新的通用且有效的方案，可以在完全非均相的条件下从吡咯和β-硝基丙烯酸酯开始合成吡咯-2-乙酸衍生物。
• β-Nitroacrylates as Precursors of Tetrasubstituted Furans in a One-Pot Process and under Acidic Solvent-Free Conditions
  作者：Alessandro Palmieri、Roberto Ballini、Serena Gabrielli

  DOI：10.1055/s-0030-1258031

  日期：2010.10

  The reaction of α-functionalized carbonyl derivatives with β-nitroacrylates, catalyzed by acidic alumina and in the absence of solvent, allows the one-pot synthesis of tetrasubstituted furan derivatives, in which at least two powerful functionalities are present in the 3- and 4-positions.

  在酸性氧化铝的催化下，δ官能化的羰基衍生物与δ-硝基丙烯酸酯在无溶剂的条件下发生反应，从而实现了四取代呋喃衍生物的一次合成，其中在 3 位和 4 位至少存在两个强力官能团。
• Solvent-Free, <i>anti</i>-Michael Addition of Active Methylene Derivatives to β-Nitroacrylates: Eco-Friendly, Chemoselective Synthesis of Polyfunctionalized Nitroalkanes
  作者：Roberto Ballini、Giovanna Bosica、Alessandro Palmieri、Khadijeh Bakhtiari

  DOI：10.1055/s-0028-1087515

  日期：——

  The chemoselective, anti-Michael addition of active ­methylene derivatives to β-nitroacrylates can be easily performed at room temperature, under solvent-free conditions, using a catalytic amount of potassium carbonate as heterogeneous catalyst.

  使用催化量的碳酸钾作为异相催化剂，可在室温、无溶剂条件下轻松实现活性亚甲基衍生物与δ-硝基丙烯酸酯的化学选择性反迈克尔加成。
• A New One-Pot Synthesis of Quinoline-2-carboxylates under Heterogeneous Conditions
  作者：Serena Gabrielli、Alessandra Giardinieri、Susanna Sampaolesi、Roberto Ballini、Alessandro Palmieri

  DOI：10.3390/molecules21060776

  日期：——

  biologically active molecules, as well as useful ligands in metal-catalyzed reactions. Herein, we present a new one-pot protocol for synthesizing this class of derivatives starting from β-nitroacrylates and 2-aminobenzaldehydes. In order to optimize the protocol, we investigated several reaction conditions, obtaining the best results using the 2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine

  喹啉-2-羧酸盐是喹啉衍生物的重要子类，主要存在于各种生物活性分子中，以及在金属催化的反应中有用的配体。在这里，我们提出了一种新的一锅法，用于从β-硝基丙烯酸酯和2-氨基苯甲醛开始合成这类衍生物。为了优化方案，我们研究了几种反应条件，使用2-叔丁基丁-2--2-二乙基氨基-1,3-二甲基过氢-1,3,2-二氮杂磷（BEMP）作为固体碱，获得了最佳结果。乙腈。最后，我们证明了我们的方法在几种底物上的通用性，从而导致以良好的总收率合成了大量官能化的喹啉-2-羧酸酯衍生物。