(+/-)-3-(1'-nitropropyl)cyclopentanone | 344751-82-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (+/-)-3-(1'-nitropropyl)cyclopentanone
• 英文别名: 3-(1-nitropropyl)cyclopentanone；3-(1-nitropropyl)cyclopentan-1-one
• CAS: 344751-82-2
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: ZXRNIGTWOAUHIG-UHFFFAOYSA-N

物化性质

• 沸点：
  294.6±13.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇 、 硝基丙烷 在 四(三苯基膦)钯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.1h， 以60%的产率得到(+/-)-3-(1'-nitropropyl)cyclopentanone
  参考文献：
  名称：

  Unusual regioselectivity in Pd(0)-catalyzed coupling of allylic monoacetates and nitroalkanes: one-pot isomerization–alkylation

  摘要：

  A hitherto unknown palladium-catalyzed reaction of nitroalkanes with hydroxy allylic acetates is reported. The reaction led to the formation of gamma-nitrocarbonyl Compounds instead of the usual unsaturated nitroalcohol expected upon displacement of the allylic acetate group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.025

文献信息

• Solvent-Free Henry and Michael Reactions with Nitroalkanes Promoted by Potassium Carbonate as a Versatile Heterogeneous Catalyst
  作者：Giovanna Bosica、Kurt Polidano

  DOI：10.1155/2017/6267036

  日期：——

  The use of a simple weak inorganic base such as potassium carbonate facilitated the formation of carbon-carbon bonds through both the Henry and the Michael reactions with nitrocompounds. The application of this catalyst under environmentally friendly solventless heterogeneous conditions gave satisfactory to good yields of β-nitroalcohols, involving aliphatic and aromatic starting materials, as well

  使用简单的弱无机碱（例如碳酸钾）通过与硝基化合物的亨利和迈克尔反应促进了碳-碳键的形成。该催化剂在环境友好的无溶剂多相条件下的应用使β-硝基醇的产率令人满意，涉及脂肪族和芳香族起始原料，以及使用几种不同的迈克尔受体和硝基烷烃形成迈克尔加合物的产率很高。
• Asymmetric conjugate addition of nitroalkanes to enones with a chiral α-aminophosphonate catalyst
  作者：Marcus Malmgren、Johan Granander、Mohamed Amedjkouh

  DOI：10.1016/j.tetasy.2008.07.007

  日期：2008.8

  Chiral diethyl (2R)-tetrahydropyrro-2-ylphosphonate is an effective catalyst for the Michael addition of nitroalkanes to alpha,beta-unsaturated ketones. This Study revealed that the hydrate salt of this alpha-aminophosphonate was found to be a better catalytic species. Moderate to high enantioselectivities were achieved in reactions that tolerate various nitroalkanes and enones in the presence of low loading of both catalyst ( 10 mol %) and bulk base (25 mol %). (C) 2008 Published by Elsevier Ltd.
• Kadas, I.; Morvai-Kadas, V.; Toeke, L., Acta Chimica Hungarica, 1983, vol. 113, # 3, p. 303 - 308
  作者：Kadas, I.、Morvai-Kadas, V.、Toeke, L.

  DOI：——

  日期：——
• KADAS, I.;MORVAI-KADAS, V.;TOKE, L., ACTA CHIM. HUNG., 1983, 113, N 3, 303-307
  作者：KADAS, I.、MORVAI-KADAS, V.、TOKE, L.

  DOI：——

  日期：——