(+/-)-3-(1'-nitropropyl)cyclohexanone

• 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)cyclohexanone
• 英文别名: 3-(1-nitropropyl)-1-cyclohexanone；3-[1-nitropropyl]cyclohexanone；3-(1-Nitropropyl)cyclohexan-1-one
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: DCMXSTJIUDEKDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1,3-二噻烷-2-基)膦酸二乙酯 、 (+/-)-3-(1'-nitropropyl)cyclohexanone 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 2-{(3S)-[1-nitropropyl]cyclohexylidene}-1,3-dithiane
  参考文献：
  名称：

  Substrate-Controlled and Organocatalytic Asymmetric Synthesis of Carbocyclic Amino Acid Dipeptide Mimetics

  摘要：

  The asymmetric synthesis of a carbocyclic delta-amino acid representing the P-2/P-3 subunit of a nonpeptidic truncated peptidomimetic molecule is described relying on two independent approaches.

  DOI：

  10.1021/jo100017t
• 作为产物：
  描述：

  2-环己烯-1-酮 、 硝基丙烷 在 potassium carbonate 作用下， 以 neat (no solvent) 为溶剂， 反应 8.0h， 以84%的产率得到(+/-)-3-(1'-nitropropyl)cyclohexanone
  参考文献：
  名称：

  碳酸钾作为多功能多相催化剂促进无溶剂亨利和迈克尔与硝基烷烃的反应

  摘要：

  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。

  DOI：

  10.1155/2017/6267036

文献信息

• Michael Additions Catalysed by N,N-dimethyl-3-aminopropyl - Derivatised Amorphous Silica and Hexagonal Mesoporous Silica (HMS)
  作者：James E. G. Mdoe、James H. Clark、Duncan J. Macquarrie

  DOI：10.1055/s-1998-1731

  日期：1998.6

  Solid bases prepared by derivatisation of amorphous silica and hexagonal mesoporous silica with dimethylaminopropyl groups are good catalysts for Michael addition reactions. Of the prepared catalysts, those based on hexagonal mesoporous silica show particularly high activities. The sol-gel method used in preparing the catalysts based on hexagonal mesoporous silica enables loading to be increased to more than twice that of those based on amorphous silica which are prepared by the post-modification method.

  通过用二甲氨基丙基对无定形二氧化硅和六方介孔二氧化硅进行衍生化制备的固体基底，是Michael加成反应的良好催化剂。在这些制备的催化剂中，基于六方介孔二氧化硅的催化剂显示出特别高的活性。在制备基于六方介孔二氧化硅的催化剂过程中使用的溶胶-凝胶方法，使得载量能够增加到基于无定形二氧化硅的催化剂的两倍以上，后者是通过后修饰方法制备的。
• P(RNCH₂CH₂)₃N:  Efficient 1,4-Addition Catalysts
  作者：Philip B. Kisanga、Palanichamy Ilankumaran、Brandon M. Fetterly、John G. Verkade

  DOI：10.1021/jo010228k

  日期：2002.5.1

  The 1,4-addition of primary alcohols, higher nitroalkanes, and a Schiff's base of an alpha-amino ester to alpha,beta-unsaturated substrates produces the corresponding products in moderate to excellent yields when carried out at -63 to 70 degreesC in the presence of catalytic amounts of the nonionic strong bases P(RNCH2CH2)(3)N (R = Me, i-Pr, i-Bu) in isobutyronitrile. Diastereoselectivity for the anti form of the product is high in the case of the Schiff's base in the absence of lithium ion. These catalysts are easily removed from the product by either column filtration through silica gel or via aqueous workup.
• 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.
• Cetyltrimethylammonium hydroxide (CTAOH) as a general, ecofriendly catalyst for the formation of carbon–carbon bond through nitroalkanes
  作者：Roberto Ballini、Dennis Fiorini、Maria Victoria Gil、Alessandro Palmieri

  DOI：10.1016/j.tet.2004.01.067

  日期：2004.3

  Nitroalkanes have been found to give good yields in Michael and nitroaldol (Henry) reactions by the use of a catalytic amount (10 mol%) of CTAOH. at room temperature and under solvent free conditions and in very short reaction times. The methods do not need a large excess of the nitroalkanes and show good chemoselectivity toward further functionalities. (C) 2004 Elsevier Ltd. All rights reserved.
• KOZLOV N. S.; GLADKIX L. V., VESTSI AN BSSR. CEP. XIM. N., IZV. AN BSSR. CEP. XIM. N., 1979, HO 4, 127+
  作者：KOZLOV N. S.、 GLADKIX L. V.

  DOI：——

  日期：——