methyl 3α-N-(3,5-dimethylbenzoyl)amino-12α-hydroxy-5β-cholan-24-oate | 403607-35-2

• 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: methyl 3α-N-(3,5-dimethylbenzoyl)amino-12α-hydroxy-5β-cholan-24-oate
• CAS: 403607-35-2
• 化学式: C₃₄H₅₁NO₄
• 分子量: 537.783
• InChiKey: NHMJRTWIWZEUMH-JPEMHBERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3α-N-(3,5-dimethylbenzoyl)amino-12α-hydroxy-5β-cholan-24-oate 在 lithium hydroxide 、 三正丁胺 、 氯甲酸乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 甲苯 为溶剂， 反应 28.17h， 生成 N-allyl-N'-methyl-3α-N-(3,5-dimethylbenzoyl)amino-12α-(3,5-dimethylphenyl)carbamoyloxy-5β-cholan-24-amide
  参考文献：
  名称：

  Synthesis of deoxycholic-derived chiral stationary phases possessing both arylcarbamate and arylamide moieties: evaluation of their chiral discrimination properties in the HPLC resolution of racemic compounds

  摘要：

  Two families of chiral selectors derived from deoxycholic acid, possessing both an arylamide and an arylcarbamate group on the cholestanic backbone were synthesized and covalently bonded to silica gel to afford new chiral stationary phases (CSPs A1-D1 and A2-D2) for the HPLC resolution of racemic compounds. The chromatographic data concerning the resolution of selected racemic compounds on CSPs A1-D1 and A2-D2 were compared with those obtained using analogous CSPs possessing only arylcarbamate groups on the cholestanic system (CSPs A-D). This has allowed its to establish that the resolution capability of CSPs A1-D1 and A2-D2 depends not only on the position of the arylamide group on the cholestanic backbone, but also on the electronic characteristics of the aromatic substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00490-6
• 作为产物：
  描述：

  去氧胆酸 在 palladium on activated charcoal 盐酸 、 sodium azide 、 氢气 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~40.0 ℃ 、861.26 kPa 条件下， 反应 100.0h， 生成 methyl 3α-N-(3,5-dimethylbenzoyl)amino-12α-hydroxy-5β-cholan-24-oate
  参考文献：
  名称：

  Synthesis of deoxycholic-derived chiral stationary phases possessing both arylcarbamate and arylamide moieties: evaluation of their chiral discrimination properties in the HPLC resolution of racemic compounds

  摘要：

  Two families of chiral selectors derived from deoxycholic acid, possessing both an arylamide and an arylcarbamate group on the cholestanic backbone were synthesized and covalently bonded to silica gel to afford new chiral stationary phases (CSPs A1-D1 and A2-D2) for the HPLC resolution of racemic compounds. The chromatographic data concerning the resolution of selected racemic compounds on CSPs A1-D1 and A2-D2 were compared with those obtained using analogous CSPs possessing only arylcarbamate groups on the cholestanic system (CSPs A-D). This has allowed its to establish that the resolution capability of CSPs A1-D1 and A2-D2 depends not only on the position of the arylamide group on the cholestanic backbone, but also on the electronic characteristics of the aromatic substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00490-6