ethyl 2-acetyl-3-(4-chlorophenyl)-4-nitrobutanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-acetyl-3-(4-chlorophenyl)-4-nitrobutanoate
• 化学式: C₁₄H₁₆ClNO₅
• 分子量: 313.738
• InChiKey: AWWYGAUBSAZMMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetyl-3-(4-chlorophenyl)-4-nitrobutanoate 、 5-styryl-4-nitro-3-methylisoxazole 在 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 48.0h， 以149 mg的产率得到
  参考文献：
  名称：

  Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters

  摘要：

  一种新的立体选择性有机催化一锅法1,4-/1,6-/1,2-加成反应，依次由低负载的方酰胺和非手性碱催化，直接进入异恶唑基环己烷，产率高且立体选择性优异，具有六个相邻立体中心。

  DOI：

  10.1039/c4cc09730k
• 作为产物：
  描述：

  4-氯苯甲醛 在 4-(triphenylphosphonio)phenolate 、 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 ethyl 2-acetyl-3-(4-chlorophenyl)-4-nitrobutanoate
  参考文献：
  名称：

  Tetraarylphosphonium inner-salts (TAPIS) as both Lewis base catalyst and phase tag

  摘要：

  Tetraarylphosphonium inner-salts (TAPIS) have been designed, synthesized and verified as recyclable and reusable Lewis base catalysts. The resulted TAPIS catalyst has been successfully applied in Michael addition, cyanation and trifluoromethylation reactions. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.06.015

文献信息

• One pot domino reaction accessing γ-nitroesters: synthesis of GABA derivatives
  作者：Fabricio F. Naciuk、Debora Z. Vargas、Caroline R. M. D'Oca、Celso C. Moro、Dennis Russowsky

  DOI：10.1039/c4nj01552e

  日期：——

  γ-Nitroesters are synthesized by theone potdomino process. GABA derivatives phenibut and baclofen were readily accessed.

  γ-硝基酯通过一锅法多米诺过程合成。GABA衍生物苯硫胺和巴克洛芬可以轻松获得。
• Acidic Alumina as a Useful Heterogeneous Catalyst in the Michael Reaction of β-Dicarbonyl Derivatives with Conjugated Nitroalkenes
  作者：Roberto Ballini、Raimondo Maggi、Alessandro Palmieri、Giovanni Sartori

  DOI：10.1055/s-2007-983897

  日期：2007.10

  Addition of a variety of 1,3-dicarbonyl derivatives to conjugated nitroalkenes was efficiently performed under heterogeneous catalysis by acidic alumina in the presence of a minimum amount of solvent (Et2O, 0.5 mL/mmol). The procedure allows satisfactory to good yields of a diastereomeric mixture (˜1:1) of polyfunctionalized adducts. Moreover, work-up can be avoided since the reaction mixture can be directly charged into a chromatographic column for immediate purification.

  在酸性氧化铝的异相催化下，在最低溶剂用量（Et2O，0.5 mL/mmol）的存在下，多种 1,3-二羰基衍生物与共轭硝基烯的加成反应得以高效进行。该方法可以获得令人满意的多官能团化加合物非对映混合物（Ë1:1）。此外，由于反应混合物可直接进入色谱柱进行即时纯化，因此可以避免返工。
• The lipase-catalyzed asymmetric C–C Michael addition
  作者：Jian-Feng Cai、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.molcatb.2010.11.011

  日期：2011.3

  The example of enzyme-catalyzed asymmetric C-C Michael addition was observed using Lipozyme TLIM (immobilized lipase from Thermomyces lanuginosus) in organic medium in the presence of water. This biocatalysis is applicable to the Michael additions of a wide range of 1,3-dicarbonyl compounds and cyclohexanone to aromatic and heteroaromatic nitroolefins and cyclohexenone. The enantioselectivities up to 83% ee and yields up to 90% were achieved. The enzyme can be reused for three cycles. (C) 2010 Elsevier B.V. All rights reserved.
• Agarwal, Jyoti; Naganaboina, Ram Tilak; Peddinli, Rama Krishna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 4, p. 511 - 518
  作者：Agarwal, Jyoti、Naganaboina, Ram Tilak、Peddinli, Rama Krishna

  DOI：——

  日期：——
• Tris-ureas as versatile and highly efficient organocatalysts for Michael addition reactions of nitro-olefins: Mechanistic insight from in-situ diagnostics
  作者：Milan Bera、Tamal Kanti Ghosh、Bidyut Akhuli、Pradyut Ghosh

  DOI：10.1016/j.molcata.2015.01.004

  日期：2015.11

  Tris(2-aminoethyl)-amine, TREN based tris-ureas (1a-1d) and tris-thiourea (1e) have been explored towards a wide range of catalytic Michael addition reactions. These tris-ureas, 1a-1d efficiently catalyze the addition reaction of beta-nitro styrenes (2a-2d) with various nucleophiles such as beta-ketoesters (3a-3c), 1,3-dicarbonyl compound (3d), a cyanoester (3e) and a nitroester (3f) under ambient conditions to produce corresponding nitro alkanes in high yields. Pentafluorophenyl attached tris-urea, 1d is found to be the most effective catalyst in the series that yields 78-98% products conversion. In case of the reaction between beta-nitro styrenes and malononitrile (3g) in presence of 1d, 2-amino-5-nitro-4,6-diphenylcyclohex-1-ene-1,3,3-tricarbonitriles are also isolated as a minor product along with the corresponding Michael adduct. The added advantage of bridge-head nitrogen center in tris-urea organocatalysts, 1a-1d has been established by studying analogous benzene platform based tris-ureas (1f, 1g, 1h) in similar experimental conditions. Furthermore, a plausible reaction mechanism has also been established based on in-situ H-1 NMR kinetic studies. (C) 2015 Elsevier B.V. All rights reserved.