(+)-3-(1-nitrocyclopentyl) cyclohexanone | 803706-21-0

• 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-nitrocyclopentyl) cyclohexanone
• 英文别名: (3R)-3-(1-nitrocyclopentyl)cyclohexan-1-one
• CAS: 803706-21-0
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: OUMCZSZGZWZTEA-SECBINFHSA-N

物化性质

• 沸点：
  343.3±31.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 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 、 (+)-3-(1-nitrocyclopentyl) cyclohexanone 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Optimization of the Catalytic Asymmetric Addition of Nitroalkanes to Cyclic Enones with trans-4,5-Methano-l-proline

  摘要：

  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).

  DOI：

  10.1021/ol0618407
• 作为产物：
  描述：

  2-环己烯-1-酮 、 硝基环戊烷 在 trans-4,5-methano-L-proline 氯仿 、 2,5-dimethyl-piperazine 作用下， 反应 141.0h， 以93%的产率得到(+)-3-(1-nitrocyclopentyl) cyclohexanone
  参考文献：
  名称：

  Optimization of the Catalytic Asymmetric Addition of Nitroalkanes to Cyclic Enones with trans-4,5-Methano-l-proline

  摘要：

  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).

  DOI：

  10.1021/ol0618407

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。
• Catalytic Asymmetric Conjugate Addition of Nitroalkanes to Cycloalkenones
  作者：Stephen Hanessian、Vinh Pham

  DOI：10.1021/ol000170g

  日期：2000.9.1

  Nitroalkanes add to cyclic and acyclic enones in an enantioselective manner in the presence of catalytic quantities of L-proline and trans-2,5-dimethylpiperazine as excess additive.

  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。
• Trends in Asymmetric Michael Reactions Catalysed by Tripeptides in Combination with an Achiral Additive in Different Solvents
  作者：Svetlana B. Tsogoeva、Sunil B. Jagtap、Zoya A. Ardemasova、Victor N. Kalikhevich

  DOI：10.1002/ejoc.200400243

  日期：2004.10

  as chiral catalysts for asymmetric Michael addition reactions in the presence of an achiral additive has been tested in different solvents (CHCl3, acetone, DMF, DMSO and the room-temperature ionic liquid [bmim]PF6). The dependence of yields and enantiomeric excesses on the solvent used has been demonstrated. The experiments show that the combination of additive and peptides provides a catalytic system

  在不同溶剂（CHCl3、丙酮、DMF、DMSO 和室温离子液体 [bmim]PF6）中测试了三肽 3、6 和 12 作为手性催化剂在非手性添加剂存在下进行不对称迈克尔加成反应的潜力. 已经证明了收率和对映体过量对所用溶剂的依赖性。实验表明，添加剂和肽的组合提供了一个似乎比其各部分总和更好的催化系统。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• 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.
• 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).