(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

• Synthesis and evaluation of guanidinyl pyrrolidines as bifunctional catalysts for enantioselective conjugate additions to cyclic enones
  作者：Sunil V. Pansare、Rajinikanth Lingampally

  DOI：10.1039/b812038b

  日期：——

  Guanidinyl pyrrolidines derived from ‘S’-proline are effective catalysts for the enantioselective conjugate addition of malonate, nitroalkane and other carbon and heteroatom nucleophiles to cyclohexenone and cyclopentenone in the absence of basic additives. The stereoselectivity is strongly dependant on catalyst loading as well as reaction concentration.

  衍生自“ S ”-脯氨酸的胍基吡咯烷是将丙二酸酯，硝基烷和其他碳原子和杂原子亲核试剂对映选择性共轭加成的有效催化剂。环己烯酮 和 环戊烯酮在没有碱性添加剂的情况下。立体选择性很大程度上取决于催化剂的负载以及反应浓度。
• 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.