(2R,5S)-2,5-diisopropylcyclohexanone | 1214747-73-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,5S)-2,5-diisopropylcyclohexanone
• 英文别名: (2R,5S)-2,5-di(propan-2-yl)cyclohexan-1-one
• CAS: 1214747-73-5
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: YRDRNKWYKZLIAE-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R,5S)-2,5-diisopropylcyclohexanone 、 2-氨基苯甲腈 在 三氟化硼乙醚 、 水 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以48%的产率得到(1R,4R)-9-amino-1,4-diisopropyl-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones

  摘要：

  This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3 center dot Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.039
• 作为产物：
  描述：

  (2R,5S)-2-isopropyl-5-(propen-2-yl)-cyclohexanone 在 platinum(IV) oxide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到(2R,5S)-2,5-diisopropylcyclohexanone
  参考文献：
  名称：

  Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones

  摘要：

  This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3 center dot Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.039

文献信息

• SYNTHESIS AND APPLICATION OF CHIRAL SUBSTITUTED POLYVINYLPYRROLIDINONES
  申请人：Kansas State University Research Foundation

  公开号：US20200306737A1

  公开（公告）日：2020-10-01

  Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery.

  手性聚乙烯吡咯烷酮（CSPVP），CSPVP与金属纳米团簇催化剂等核心物种形成的络合物，以及利用这种络合物进行对映选择氧化反应的方法被揭示。CSPVP络合物可用于不对称二醇氧化、烯烃对映选择氧化以及碳-碳键形成反应等。CSPVP还可以与蛋白质、DNA和RNA等生物分子形成络合物，并用作siRNA或dsRNA传递的纳米载体。
• Chiral-Substituted Poly-<i>N</i>-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions
  作者：Bo Hao、Medha J. Gunaratna、Man Zhang、Sahani Weerasekara、Sarah N. Seiwald、Vu T. Nguyen、Alex Meier、Duy H. Hua

  DOI：10.1021/jacs.6b12113

  日期：2016.12.28

  synthesized from l-amino acids. The polymers, particularly 17, were used to stabilize nanoclusters such as Pd/Au for the catalytic asymmetric oxidations of 1,3- and 1,2-cycloalkanediols and alkenes, and Cu/Au was used for C-H oxidation of cycloalkanes. It was found that the bulkier the C5 substituent in the pyrrolidinone ring, the greater the optical yields produced. Both oxidative kinetic resolution of (±)-1

  由L-氨基酸合成了在吡咯烷酮环的C5处含有不对称中心的一类新的聚-N-乙烯基吡咯烷酮。这些聚合物，特别是17，用于稳定纳米团簇，例如Pd/Au，用于1,3-和1,2-环烷二醇和烯烃的催化不对称氧化，而Cu/Au用于环烷烃的CH氧化。研究发现，吡咯烷酮环中的C5取代基体积越大，产生的光学产率越大。 (±)-1,3- 和 1,2-反式环烷二醇的氧化动力学拆分以及内消旋顺式二醇的去对称化均在水中的氧气气氛下用 0.15 mol% Pd/Au (3:1)-17 进行，提供优异的 (S)-羟基酮的化学和光学收率。在 30 psi 氧气水中，用 0.5 mol% Pd/Au (3:1)-17 氧化各种烯烃，得到 >93% ee 的二羟基化产物。 (R)-柠檬烯在 25 °C 下在 C-1,2-环烯官能团处发生氧化，产生 (1S,2R,4R)-二羟基柠檬烯 49，产率 92%。重要的是，环烷烃用乙腈中的
• Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones
  作者：Diego dos Santos Pisoni、Jessie Sobieski da Costa、Douglas Gamba、Cesar Liberato Petzhold、Antonio César de Amorim Borges、Marco Antonio Ceschi、Paula Lunardi、Carlos Alberto Saraiva Gonçalves

  DOI：10.1016/j.ejmech.2009.10.039

  日期：2010.2

  This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3 center dot Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested. (C) 2009 Elsevier Masson SAS. All rights reserved.