(1'R,3S)-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: (1'R,3S)-3-(1'-nitropropyl)cyclohexanone
• 英文别名: (3S)-[(1R-nitropropyl)]cyclohexanone；(3S)-3-[(1R)-1-nitropropyl]cyclohexan-1-one
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: DCMXSTJIUDEKDG-IONNQARKSA-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'R,3S)-3-(1'-nitropropyl)cyclohexanone 、 (2R,3R)-(-)-2,3-丁二醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 4.0h， 以236.9 mg的产率得到(2R,3R,7S)-2,3-Dimethyl-7-((R)-1-nitro-propyl)-1,4-dioxa-spiro[4.5]decane
  参考文献：
  名称：

  在相转移条件下，N-螺环手性季铵溴化铵催化硝基烷的非对映和对映选择性共轭加成反应。

  摘要：

  [反应，结构：见正文]已发现，具有3,5-bis（3,3,3-在固-液相转移条件下的4,5-三氟苯基）苯基取代基以优异的化学收率得到前所未有的非对映和对映体控制水平，从而提供相应的γ-硝基酮。

  DOI：

  10.1021/ol0517170
• 作为产物：
  描述：

  2-环己烯-1-酮 、 硝基丙烷 在 N-spiro C₂-symmetric chiral quaternary ammonium bromide caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 0.67h， 生成 3-(1-nitro-propyl)-cyclohexanone 、 3-(1-nitro-propyl)-cyclohexanone 、 (1'S,3S)-3-(1'-nitropropyl)cyclohexanone 、 (1'R,3S)-3-(1'-nitropropyl)cyclohexanone
  参考文献：
  名称：

  在相转移条件下，N-螺环手性季铵溴化铵催化硝基烷的非对映和对映选择性共轭加成反应。

  摘要：

  [反应，结构：见正文]已发现，具有3,5-bis（3,3,3-在固-液相转移条件下的4,5-三氟苯基）苯基取代基以优异的化学收率得到前所未有的非对映和对映体控制水平，从而提供相应的γ-硝基酮。

  DOI：

  10.1021/ol0517170

文献信息

• Optimization of the Catalytic Asymmetric Addition of Nitroalkanes to Cyclic Enones with <i>trans</i>-4,5-Methano-<scp>l</scp>-proline
  作者：Stephen Hanessian、Zhihui Shao、Jayakumar S. Warrier

  DOI：10.1021/ol0618407

  日期：2006.10.1

  The conjugate addition of symmetrical 2-nitroalkanes to 2-cycloalkenones catalyzed by trans-4,5-methano-L-proline proceeds with > 99% ee and excellent chemical yields. 1-Nitroalkanes afford diastereomeric syn/anti products that can be separated with good individual enantioselectivities. Proline hydroxamic acid and its trans-4,5-methano-L-proline hydroxamic acid are also effective organocatalysts in the addition of 2-nitropropane to 2-cyclohexenone (75% and 81% ee, respectively).
• 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.
• Substrate-Controlled and Organocatalytic Asymmetric Synthesis of Carbocyclic Amino Acid Dipeptide Mimetics
  作者：Stephen Hanessian、Dilip K. Maji、Subramaniyan Govindan、Riccardo Matera、Marina Tintelnot-Blomley

  DOI：10.1021/jo100017t

  日期：2010.5.7

  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.
• <i>N</i>-Spiro Chiral Quaternary Ammonium Bromide Catalyzed Diastereo- and Enantioselective Conjugate Addition of Nitroalkanes to Cyclic α,β-Unsaturated Ketones under Phase-Transfer Conditions
  作者：Takashi Ooi、Saki Takada、Shingo Fujioka、Keiji Maruoka

  DOI：10.1021/ol0517170

  日期：2005.11.1

  [reaction, structure: see text] Conjugate addition of various prochiral nitroalkanes to cyclic alpha,beta-unsaturated ketones was found to be efficiently catalyzed by N-spiro C2-symmetric chiral quaternary ammonium bromide 1b possessing a 3,5-bis(3,4,5-trifluorophenyl)phenyl substituent under solid-liquid phase-transfer conditions to afford the corresponding gamma-nitro ketones in excellent chemical yields

  [反应，结构：见正文]已发现，具有3,5-bis（3,3,3-在固-液相转移条件下的4,5-三氟苯基）苯基取代基以优异的化学收率得到前所未有的非对映和对映体控制水平，从而提供相应的γ-硝基酮。