(R)-3-(2-nitropropan-2-yl)cyclopentanone

• 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: (R)-3-(2-nitropropan-2-yl)cyclopentanone
• 英文别名: 3-(2-nitropropane-2-yl)-cyclopentanone；(+)-3-(2-nitropropyl) cyclopentanone；(3R)-3-(2-nitropropan-2-yl)cyclopentan-1-one
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: RAVVCAMCOPUWJX-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 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

• 作为反应物：
  描述：

  (2R,3R)-(-)-2,3-丁二醇 、 (R)-3-(2-nitropropan-2-yl)cyclopentanone 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 (2R,3R,7R)-2,3-Dimethyl-7-(1-methyl-1-nitro-ethyl)-1,4-dioxa-spiro[4.4]nonane 、 (2R,3R,7S)-2,3-Dimethyl-7-(1-methyl-1-nitro-ethyl)-1,4-dioxa-spiro[4.4]nonane
  参考文献：
  名称：

  硝基烷烃向环烯酮的催化不对称共轭加成反应。

  摘要：

  在催化量的L-脯氨酸和反式2,5-二甲基哌嗪作为过量添加剂存在下，硝基烷以对映选择性的方式添加到环状和无环烯酮中。

  DOI：

  10.1021/ol000170g
• 作为产物：
  描述：

  2-环戊烯酮 、 2-硝基丙烷 在 cis-2,5-Dimethyl-piperidin 、 (S)-5-(吡咯烷-2-基)-1H-四唑 作用下， 以 二氯甲烷 为溶剂， 反应 504.0h， 生成 (R)-3-(2-nitropropan-2-yl)cyclopentanone 、 (S)-3-(2-nitropropan-2-yl)cyclopentanone
  参考文献：
  名称：

  一种多用途的有机催化剂，用于硝基烷烃向烯酮的不对称共轭加成。

  摘要：

  5-吡咯烷基-2-基四唑用作改进的催化剂，用于将一系列硝基烷烃不对称地加成至环状和非环状烯酮中，具有良好至优异的对映选择性。

  DOI：

  10.1039/b511441a

文献信息

• A versatile organocatalyst for the asymmetric conjugate addition of nitroalkanes to enones
  作者：Claire E. T. Mitchell、Stacey E. Brenner、Steven V. Ley

  DOI：10.1039/b511441a

  日期：——

  5-Pyrrolidin-2-yltetrazole performs as an improved catalyst for the asymmetric addition of a range of nitroalkanes to cyclic and acyclic enones, with good to excellent enantioselectivity.

  5-吡咯烷基-2-基四唑用作改进的催化剂，用于将一系列硝基烷烃不对称地加成至环状和非环状烯酮中，具有良好至优异的对映选择性。
• 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。
• 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.
• 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.