(1R,4R)-1-((S)-1-hydroxy-2-(piperidin-1-yl)ethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one

• 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: (1R,4R)-1-((S)-1-hydroxy-2-(piperidin-1-yl)ethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one
• 英文别名: (1R,4R)-1-[(1S)-1-hydroxy-2-(1-piperidyl)ethyl]-7,7-dimethyl-norbornan-2-one；(1R,4R)-1-[(1S)-1-hydroxy-2-piperidin-1-ylethyl]-7,7-dimethylbicyclo[2.2.1]heptan-2-one
• 化学式: C₁₆H₂₇NO₂
• 分子量: 265.396
• InChiKey: HBXPJSRVQDQRSN-XPKDYRNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4R)-1-((S)-1-hydroxy-2-(piperidin-1-yl)ethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以30%的产率得到
  参考文献：
  名称：

  Highly efficient synthesis of chiral aminoalcohols and aminodiols with camphane skeleton

  摘要：

  Methylidene substituted camphor was easily epoxidized to give bridgehead oxirane-substituted camphor in the form of two diastereoisomers, isolated in pure form. These were used in aminolysis reactions with different secondary amines leading to series of chiral aminoalcohols bearing a ketone functionality. The latter could be reduced by using LAH or DIBAL to a series of aminodiols. For the determination of the configuration of the newly formed stereogenic centre, advanced NMR experiments and X-ray crystallography were used. The new aminoalcohols and aminodiols were tested as pre-catalysts for the enantioselective addition of Et2Zn to benzaldehyde showing moderate enantioselectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.08.015
• 作为产物：
  描述：

  (+)-7,7-dimethyl-1-vinyl-2-norbornanone 在 lithium perchlorate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 45.0h， 生成 (1R,4R)-1-((S)-1-hydroxy-2-(piperidin-1-yl)ethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Highly efficient synthesis of chiral aminoalcohols and aminodiols with camphane skeleton

  摘要：

  Methylidene substituted camphor was easily epoxidized to give bridgehead oxirane-substituted camphor in the form of two diastereoisomers, isolated in pure form. These were used in aminolysis reactions with different secondary amines leading to series of chiral aminoalcohols bearing a ketone functionality. The latter could be reduced by using LAH or DIBAL to a series of aminodiols. For the determination of the configuration of the newly formed stereogenic centre, advanced NMR experiments and X-ray crystallography were used. The new aminoalcohols and aminodiols were tested as pre-catalysts for the enantioselective addition of Et2Zn to benzaldehyde showing moderate enantioselectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.08.015

文献信息

• Highly efficient synthesis of chiral aminoalcohols and aminodiols with camphane skeleton
  作者：Malinka P. Stoyanova、Boris L. Shivachev、Rosica P. Nikolova、Vladimir Dimitrov

  DOI：10.1016/j.tetasy.2013.08.015

  日期：2013.11

  Methylidene substituted camphor was easily epoxidized to give bridgehead oxirane-substituted camphor in the form of two diastereoisomers, isolated in pure form. These were used in aminolysis reactions with different secondary amines leading to series of chiral aminoalcohols bearing a ketone functionality. The latter could be reduced by using LAH or DIBAL to a series of aminodiols. For the determination of the configuration of the newly formed stereogenic centre, advanced NMR experiments and X-ray crystallography were used. The new aminoalcohols and aminodiols were tested as pre-catalysts for the enantioselective addition of Et2Zn to benzaldehyde showing moderate enantioselectivity. (C) 2013 Elsevier Ltd. All rights reserved.
• Antimycobacterial activity of chiral aminoalcohols with camphane scaffold
  作者：Zhanina Petkova、Violeta Valcheva、Georgi Momekov、Petar Petrov、Vladimir Dimitrov、Irini Doytchinova、Georgi Stavrakov、Malinka Stoyanova

  DOI：10.1016/j.ejmech.2014.05.007

  日期：2014.6

  A series of aminoalcohols were synthesized by reaction of aminolysis of camphor derived oxiranes with chosen amines. The compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv. Ten of the new structures show much higher activity than the classical anti-TB drug ethambutol. Some of the most active compounds were tested against MDR strain 43, and four of them demonstrated excellent activities with MICs 0.27-0.72 mu M. The cytotoxicity of representative exerting antimycobacterial activity compounds was assessed. Quantitative structure activity relationship (QSAR) model is derived to estimate the contribution of each structural fragment to the activity. The camphane-based aminoalcohols are promising lead compounds for further development of novel antimycobacterial agents. (C) 2014 Elsevier Masson SAS. All rights reserved.