(1S,2S)-2-[(9-anthrylmethyl)(methyl)amino]cyclopentanol | 1112976-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (1S,2S)-2-[(9-anthrylmethyl)(methyl)amino]cyclopentanol
• 英文别名: (1S,2S)-2-[anthracen-9-ylmethyl(methyl)amino]cyclopentan-1-ol
• CAS: 1112976-75-6
• 化学式: C₂₁H₂₃NO
• 分子量: 305.42
• InChiKey: YPTAFNGEWDQKGK-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 (+/-)-trans-2-[(9-anthrylmethyl)(methyl)-amino]cyclopentanol 在 Pseudomonas cepacia lipase PSL-C 作用下， 以 甲基叔丁基醚 为溶剂， 反应 5.0h， 以47%的产率得到(1R,2R)-2-[(9-anthrylmethyl)(methyl)amino]cyclopentyl acetate
  参考文献：
  名称：

  Chemoenzymatic preparation of optically active anthracene derivatives

  摘要：

  Syntheses and lipase-catalyzed resolutions of a trans-2-aminocyclopentanol rac-2 and trans-cyclopentane-1,2-diamine rac-3, bearers of an anthracene unit, have been effectively carried out. Burkholderia cepacia lipase catalyzed the transesterification of the P-amino alcohol with very high enantioselectivity (E > 200). Lipase B from Candida antarctica showed moderate enantioselectivity in the acetylation of the diamine when 1-phenylethyl acetate was used as an acyl donor. In addition, the treatment of the optically active diamine (1S,2S)-3 (ee = 95%) with pyridine-2,6-dicarbonyl dichloride yielded the bis(aminoamide) 6, which was tested as a chiral solvating agent (CSA) of carboxylic acids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.029

文献信息

• Chemoenzymatic preparation of optically active anthracene derivatives
  作者：F. Javier Quijada、Javier González-Sabín、Francisca Rebolledo、Vicente Gotor

  DOI：10.1016/j.tetasy.2008.10.029

  日期：2008.11

  Syntheses and lipase-catalyzed resolutions of a trans-2-aminocyclopentanol rac-2 and trans-cyclopentane-1,2-diamine rac-3, bearers of an anthracene unit, have been effectively carried out. Burkholderia cepacia lipase catalyzed the transesterification of the P-amino alcohol with very high enantioselectivity (E > 200). Lipase B from Candida antarctica showed moderate enantioselectivity in the acetylation of the diamine when 1-phenylethyl acetate was used as an acyl donor. In addition, the treatment of the optically active diamine (1S,2S)-3 (ee = 95%) with pyridine-2,6-dicarbonyl dichloride yielded the bis(aminoamide) 6, which was tested as a chiral solvating agent (CSA) of carboxylic acids. (C) 2008 Elsevier Ltd. All rights reserved.