3α-aminodigoxigenin | 90360-24-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3α-aminodigoxigenin
• 英文别名: 3-[(3R,5R,8R,9S,10S,12R,13S,14S,17R)-3-amino-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• CAS: 90360-24-0
• 化学式: C₂₃H₃₅NO₄
• 分子量: 389.535
• InChiKey: NSQYQZYCHZUDAT-DYQFMBOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)生物素-N-琥珀酰亚胺基酯 、 3α-aminodigoxigenin 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Efficient synthesis of 3-aminodigoxigenin and 3-aminodigitoxigenin probes

  摘要：

  Oxidation of digoxigenin and digitoxigenin to the 3-ketones followed by reductive amination produced a mixture of amine epimers. The inability to separate the epimeric mixtures of chemiluminescent digoxigenin probes derived by conjugation to the acridinium label prompted us to develop an HPLC method to separate the amines. Labeling of the pure amines resulted in good yields of the isomerically pure probes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00079-7
• 作为产物：
  描述：

  (5beta)-12,beta,14-二羟基-3-氧代心甾-20(22)-烯内酯 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 3α-aminodigoxigenin 、 3β-aminodigoxigenin
  参考文献：
  名称：

  Efficient synthesis of 3-aminodigoxigenin and 3-aminodigitoxigenin probes

  摘要：

  Oxidation of digoxigenin and digitoxigenin to the 3-ketones followed by reductive amination produced a mixture of amine epimers. The inability to separate the epimeric mixtures of chemiluminescent digoxigenin probes derived by conjugation to the acridinium label prompted us to develop an HPLC method to separate the amines. Labeling of the pure amines resulted in good yields of the isomerically pure probes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00079-7

文献信息

• A straightforward synthesis of 3α- and 3β-aminodigoxigenin
  作者：Maciej Adamczyk、Jonathan Grote

  DOI：10.1016/s0039-128x(96)00113-4

  日期：1996.10

  Pure 3 alpha- and 3 beta-aminodigoxigenin were previously prepared from 12-acetyldigoxigenin by a multistep route involving tosylation, azide inversion, deprotection, and reduction. This paper describes the straightforward synthesis of the pure epimers in a single step via reductive amination of digoxigenone and chromatographic separation without the need for protection and deprotection. (C) 1996 by Elsevier Science Inc.