(1'R,3R)-3-(1'-nitroethyl)cyclohexanone | 804531-63-3

• 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,3R)-3-(1'-nitroethyl)cyclohexanone
• 英文别名: (3R)-3-(1-Nitroethyl)cyclohexan-1-one；(3R)-3-[(1R)-1-nitroethyl]cyclohexan-1-one
• CAS: 804531-63-3
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: UNJFNXOQUDPIMG-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硝基乙烷 、 2-环己烯-1-酮 在 2,5-dimethyl-piperazine 、 (S)-5-(吡咯烷-2-基)-1H-四唑 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (1'S,3R)-3-(1'-nitroethyl)cyclohexanone 、 (1'R,3R)-3-(1'-nitroethyl)cyclohexanone 、 (1'S,3S)-3-(1'-nitroethyl)cyclohexanone 、 (1'R,3S)-3-(1'-nitroethyl)cyclohexanone
  参考文献：
  名称：

  高效，不对称的有机催化剂介导的硝基烷烃向不饱和环状和无环酮的共轭加成反应。

  摘要：

  5-吡咯烷-2-基四唑是一种通用的有机催化剂，用于将硝基烷烃不对称地加成成烯酮。使用这种催化剂，这种转化需要较短的反应时间，可以耐受广泛的底物范围，并且可能通过生成亚胺鎓类物质进行。

  DOI：

  10.1039/b601877g

文献信息

• An efficient, asymmetric organocatalyst-mediated conjugate addition of nitroalkanes to unsaturated cyclic and acyclic ketones
  作者：Claire E. T. Mitchell、Stacey E. Brenner、Jorge García-Fortanet、Steven V. Ley

  DOI：10.1039/b601877g

  日期：——

  5-Pyrrolidin-2-yltetrazole is a versatile organocatalyst for the asymmetric conjugate addition of nitroalkanes to enones. Using this catalyst, this transformation requires short reaction times, tolerates a broad substrate scope, and possibly proceeds via generation of an iminium species.

  5-吡咯烷-2-基四唑是一种通用的有机催化剂，用于将硝基烷烃不对称地加成成烯酮。使用这种催化剂，这种转化需要较短的反应时间，可以耐受广泛的底物范围，并且可能通过生成亚胺鎓类物质进行。
• 4-trans-Amino-proline based di- and tetrapeptides as organic catalysts for asymmetric C–C bond formation reactions
  作者：Svetlana B. Tsogoeva、Sunil B. Jagtap、Zoya A. Ardemasova

  DOI：10.1016/j.tetasy.2006.03.012

  日期：2006.3

  4-trans-Amino-proline based di- and tetrapeptides have been successfully applied as chiral organocatalysts in the enantioselective conjugate addition of nitroalkanes to cyclic enones and the direct aldol reaction. Two 4-trans-amino-proline residues were shown to be sufficient enough to catalyze the conjugate addition reactions with up to 88% ee and up to 100% yield. It has been demonstrated that 4-trans-amino-proline based di- and tetrapeptides are significantly more active than L-proline (at 30 mol %) and can catalyze the direct aldol reaction with good yield and enantioselectivity within 3 h and at lower catalyst loading (5 mol %). (c) 2006 Elsevier Ltd. All rights reserved.
• 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.