ethyl 2-(1-(4-methoxyphenyl)2-nitroethyl)acetoacetate | 101106-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 2-(1-(4-methoxyphenyl)2-nitroethyl)acetoacetate
• 英文别名: ethyl 2-acetyl-3-(4-methoxyphenyl)-4-nitrobutanoate；4-Nitro-2-acetyl-3-(4-methoxy-phenyl)-buttersaeure-ethylester
• CAS: 101106-40-5
• 化学式: C₁₅H₁₉NO₆
• 分子量: 309.319
• InChiKey: TUFZYEMHIZNRCY-UHFFFAOYSA-N

物化性质

• 熔点：
  68 °C
• 沸点：
  456.1±45.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1-(4-methoxyphenyl)2-nitroethyl)acetoacetate 、 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177 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-甲氧基苯甲醛 在 4-(triphenylphosphonio)phenolate 、 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 ethyl 2-(1-(4-methoxyphenyl)2-nitroethyl)acetoacetate
  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

• Efficient Method for the Synthesis of Michael Adducts Using Kaolin Preloaded with KOH
  作者：G. Srihari、M. Marthanda Murthy

  DOI：10.1080/00397910802439191

  日期：2009.2.9

  Abstract Michael addition of various active methylene compounds to β-nitrostyrenes is efficiently catalyzed by using Kaolin preloaded with KOH in acetonitrile at room temperature with moderate to good yields.

  摘要 在室温下，在乙腈中预载 KOH 的高岭土可以有效地催化各种活性亚甲基化合物与 β-硝基苯乙烯的迈克尔加成反应，收率适中。
• 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：——
• Raghuvanshi, Raghvendra Singh; Singh, Manorama, Journal of the Indian Chemical Society, 2012, vol. 89, # 5, p. 679 - 682
  作者：Raghuvanshi, Raghvendra Singh、Singh, Manorama

  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.
• Sopova,A.S.; Temp,A.A., Journal of general chemistry of the USSR, 1961, vol. 31, p. 1420 - 1422
  作者：Sopova,A.S.、Temp,A.A.

  DOI：——

  日期：——