((1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl)(piperidin-1-yl)methanone | 851512-69-1

• 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: ((1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl)(piperidin-1-yl)methanone
• 英文别名: [(1S,2R,4R)-2-hydroxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]-piperidin-1-ylmethanone
• CAS: 851512-69-1
• 化学式: C₁₅H₂₅NO₂
• 分子量: 251.369
• InChiKey: CHHBACHLAOSHPZ-JMSVASOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl)(piperidin-1-yl)methanone 在 N,N,N,N-tetraethylammonium tetrafluoroborate 作用下， 以 乙醇 、 乙腈 为溶剂， 以67%的产率得到(1S,8S,10R,12R)-15,15-dimethyl-9-oxa-3-azatetracyclo[10.2.1.01,10.03,8]pentadecan-2-one
  参考文献：
  名称：

  Highly diastereoselective synthesis of pyrido[2,1-b][1,3]oxazin-4(6H)-one by intramolecular anodic oxidation

  摘要：

  This paper describes a method for the intramolecular anodic oxidation of omega-hydroxyl amides. Products were obtained in acceptable yields from different starting materials using various applied currents, charge, and reactant concentrations. Compounds 1a and 1d afforded a single diastereomer in 67% yield when the applied current and reactant concentration were 100 mA and 0.04 M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.017
• 作为产物：
  描述：

  1-[(1S)-ketopinyl]piperidine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 ((1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl)(piperidin-1-yl)methanone
  参考文献：
  名称：

  Highly diastereoselective synthesis of pyrido[2,1-b][1,3]oxazin-4(6H)-one by intramolecular anodic oxidation

  摘要：

  This paper describes a method for the intramolecular anodic oxidation of omega-hydroxyl amides. Products were obtained in acceptable yields from different starting materials using various applied currents, charge, and reactant concentrations. Compounds 1a and 1d afforded a single diastereomer in 67% yield when the applied current and reactant concentration were 100 mA and 0.04 M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.017

文献信息

• Hydroxyamide-catalyzed enantioselective addition of diethylzinc to benzaldehyde in the absence of titanium
  作者：Tomás de las Casas Engel、Beatriz Lora Maroto、Antonio García Martínez、Santiago de la Moya Cerero

  DOI：10.1016/j.tetasy.2008.02.025

  日期：2008.4

  Three camphor-based tertiary-amido isoborneols have been obtained from ketopinic acid and tested as ligands for the hydroxy-amide-catalyzed enantioselective addition of diethylzinc to benzaldehyde in the absence of Ti(O-i-Pr)(4). The results obtained have been compared with previous results published by Oppolzer. The new chiral ligands showed effective asymmetric activity in the absence of titanium (up to 98% yield and 90% ee). It is demonstrated that non-bulky dialkylamino groups are necessary for obtaining high chemical yields, whereas the C-2 symmetry is necessary to reach a good enantioselection level. (c) 2008 Elsevier Ltd. All rights reserved.