2-[1-(2,4-dimethoxyphenyl)-2-nitroethyl]cyclohexan-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[1-(2,4-dimethoxyphenyl)-2-nitroethyl]cyclohexan-1-one
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: AUPSEXUCHLBIKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-[1-(2,4-dimethoxyphenyl)-2-nitroethyl]cyclohexan-1-one 在 5%-palladium/activated carbon 、 氢气 、 乙烯 作用下， 以 乙醇 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以69 %的产率得到3-(2,4-dimethoxyphenyl)-1H-indole
  参考文献：
  名称：

  2-(2-硝基-1-苯乙基)环己酮衍生物一锅法合成3-取代吲哚

  摘要：

  在此，报道了由 Pd/C 催化的 2-(2-硝基-1-苯乙基) 环己酮衍生物一锅法合成 3-取代吲哚。原料可以很容易地通过取代酮和硝基烯烃的反应来制备。简便的实验程序包括在 10 mol % Pd/C 存在下使用 H 2作为氢供体处理 2-(2-硝基-1-苯乙基)环己酮衍生物。随后，H 2与作为氢受体的CH 2 =CH 2的交换以高产率提供多种3-取代的吲哚。中间硝酮的形成对于顺利反应至关重要。

  DOI：

  10.1021/acs.joc.3c00233
• 作为产物：
  描述：

  2,4-dimethoxy-β-nitro-styrene 、 环己酮 在 (S)-1-(pyrrolidin-2-ylmethoxy)-1H-benzo[d][1,2,3]triazole 作用下， 以 水 为溶剂， 反应 18.0h， 以89%的产率得到
  参考文献：
  名称：

  Pyrrolidine-HOBt: an oxytriazole catalyst for the enantioselective Michael addition of cyclohexanone to nitroolefins in water

  摘要：

  A new analogue of the proline derived organocatalyst 'pyrrolidine-HOBt' has been designed and synthesized from L-prolinol and hydroxybenzotriazole (HOBt) employing a simple reaction protocol. The catalyst was found to be effective in promoting the asymmetric Michael addition of cyclohexanone to nitroolefins using water as the reaction medium. The reaction products gamma-nitrocarbonyls are obtained in good yields and stereoselectivities. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.08.006

文献信息

• Organocatalyzed asymmetric Michael addition by an efficient bifunctional carbohydrate–thiourea hybrid with mechanistic DFT analysis
  作者：Chandra S. Azad、Imran A. Khan、Anudeep K. Narula

  DOI：10.1039/c6ob02158a

  日期：——

  core scaffold were synthesized and examined as catalysts for the asymmetric Michael addition reaction of aryl/alkyl trans-β-nitrostyrenes over cyclohexanone and other Michael donors having active methylene. Excellent enantioselectivities (<95%), diastereoselectivities (<99%), and yields (<99%) were attained under solvent free conditions using 10 mol% of 1d0. The obtained results were explained through

  合成了一系列以D-葡萄糖为核心骨架的硫脲基双功能有机催化剂，并研究了其作为芳基/烷基反式-β-硝基苯乙烯在环己酮和其他具有活性亚甲基的迈克尔供体上的不对称迈克尔加成反应的催化剂。在无溶剂条件下，使用10 mol％的1d 0可获得极好的对映选择性（<95％），非对映选择性（<99％）和产率（<99％）。通过使用B3LYP / 6-311G（d，p）// B3LYP / 6-31G（d）基本集的DFT计算来解释获得的结果。QM / MM计算揭示了在速率确定步骤中环己酮作为溶剂和反应物的作用，赋予了31.91 kcal mol -1 能量形成产品。
• Surfactant-type asymmetric organocatalyst: organocatalytic asymmetric Michael addition to nitrostyrenes in water
  作者：Sanzhong Luo、Xueling Mi、Song Liu、Hui Xu、Jin-Pei Cheng

  DOI：10.1039/b607846j

  日期：——

  A surfactant-type asymmetric organocatalyst (STAO) catalyzed highly efficient Michael addition to nitroalkenes with high stereoselectivities in water without using any organic solvents or additional additives.

  一种表面活性剂型不对称有机催化剂（STAO）在水中催化了对硝基烯烃的高效迈克尔加成反应，具有很高的立体选择性，并且无需使用任何有机溶剂或额外添加剂。
• Noncovalently Supported Heterogeneous Chiral Amine Catalysts for Asymmetric Direct Aldol and Michael Addition Reactions
  作者：Sanzhong Luo、Jiuyuan Li、Long Zhang、Hui Xu、Jin-Pei Cheng

  DOI：10.1002/chem.200701129

  日期：2008.1.28

  combinatorial screening of optimal catalysts for the targeted reactions. In this regard, highly efficient and enantioselective heterogeneous catalysts were identified for the asymmetric direct aldol and Michael addition reactions. The catalysts could be easily recovered by filtration and reused for six cycles with similar stereoselectivity but slightly decreased activity. Significantly, the deactivated

  提出了一种通过酸碱相互作用原位结合聚苯乙烯（PS）/磺酸和手性胺来固定不对称有机催化剂的新策略。PS /磺酸在催化剂的锚定和调节活性和立体选择性方面起着双重作用。检查了不同类型的聚合磺酸，发现中等载量磺酸部分的1％二乙烯基苯（DVB）交联的PS /磺酸1e是最佳载体。此外，该系统的非共价性允许组合筛选针对目标反应的最佳催化剂。在这方面，对于不对称直接的羟醛和迈克尔加成反应，已鉴定出高效且对映选择性的非均相催化剂。可以通过过滤容易地回收催化剂，并以相似的立体选择性但活性略有下降的方式重复使用六个循环。重要的是，失活的催化剂可以在酸性洗涤/胺加料程序之后再生。
• Sugar amide-pyrrolidine catalyst for the asymmetric Michael addition of ketones to nitroolefins
  作者：Togapur Pavan Kumar、Sirinyam Venugopal Balaji

  DOI：10.1016/j.tetasy.2014.02.003

  日期：2014.3

  New sugar amide-pyrrolidine derivatives possessing the furano form of the carbohydrate template were designed and developed as efficient and stereoselective organocatalysts for asymmetric Michael additions of ketones to nitroolefins at room temperature. Good yields and high selectivities were achieved with catalyst 2 under solvent-free and additive-free reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.
• Pyrrolidine-HOBt: an oxytriazole catalyst for the enantioselective Michael addition of cyclohexanone to nitroolefins in water
  作者：Togapur Pavan Kumar、Sthanikam Siva Prasad、Kothapalli Haribabu、Veerjala Naveen Kumar、Cirandur Suresh Reddy

  DOI：10.1016/j.tetasy.2016.08.006

  日期：2016.12

  A new analogue of the proline derived organocatalyst 'pyrrolidine-HOBt' has been designed and synthesized from L-prolinol and hydroxybenzotriazole (HOBt) employing a simple reaction protocol. The catalyst was found to be effective in promoting the asymmetric Michael addition of cyclohexanone to nitroolefins using water as the reaction medium. The reaction products gamma-nitrocarbonyls are obtained in good yields and stereoselectivities. (C) 2016 Elsevier Ltd. All rights reserved.