prop-2-ynyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[2-[4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[2-[4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[2-[4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2-azidoacetyl)oxy-7,12-diformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxymethyl]triazol-1-yl]acetyl]oxy-7,12-diformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxymethyl]triazol-1-yl]acetyl]oxy-7,12-diformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxymethyl]triazol-1-yl]acetyl]oxy-7,12-diformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate | 1353720-64-5

• 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: prop-2-ynyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[2-[4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[2-[4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[2-[4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2-azidoacetyl)oxy-7,12-diformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxymethyl]triazol-1-yl]acetyl]oxy-7,12-diformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxymethyl]triazol-1-yl]acetyl]oxy-7,12-diformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxymethyl]triazol-1-yl]acetyl]oxy-7,12-diformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 1353720-64-5
• 化学式: C₁₂₄H₁₇₂N₁₂O₃₂
• 分子量: 2342.79
• InChiKey: YIHFJYKXWSHSHN-YDDULYMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.4
• 重原子数：
  168
• 可旋转键数：
  59
• 环数：
  19.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  527
• 氢给体数：
  0
• 氢受体数：
  40

反应信息

• 作为产物：
  描述：

  propargyl 3α-azidoacetoxy-7α,12α-diformyloxy-5β-cholan-24-oate 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以4.6%的产率得到prop-2-ynyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[2-[4-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2-azidoacetyl)oxy-7,12-diformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]oxymethyl]triazol-1-yl]acetyl]oxy-7,12-diformyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
  参考文献：
  名称：

  Synthesis and spectroscopic studies of new bile acid derivatives linked by a 1,2,3-triazole ring

  摘要：

  A novel method for the synthesis of cholic acid derivatives has been developed using 'click chemistry'. Intermolecular 1,3-dipolar cycloaddition of the propargyl ester and azide groups of 3 alpha-azidoacetoxy-7 alpha,12 alpha-diformyloxy-5 beta-cholan-24-oate gave a new dimer and oligomer linked by a 1,2,3-triazole ring. The structures of the products were confirmed by spectral (H-1 NMR, C-13 NMR, and FT-IR) analysis, mass spectrometry and PM5 semiempirical methods. Estimation of the pharmacotherapeutic potential has been accomplished for the synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASSs). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.027

文献信息

• Synthesis and spectroscopic studies of new bile acid derivatives linked by a 1,2,3-triazole ring
  作者：Tomasz Pospieszny、Izabela Małecka、Zdzisław Paryzek

  DOI：10.1016/j.tetlet.2011.11.027

  日期：2012.1

  A novel method for the synthesis of cholic acid derivatives has been developed using 'click chemistry'. Intermolecular 1,3-dipolar cycloaddition of the propargyl ester and azide groups of 3 alpha-azidoacetoxy-7 alpha,12 alpha-diformyloxy-5 beta-cholan-24-oate gave a new dimer and oligomer linked by a 1,2,3-triazole ring. The structures of the products were confirmed by spectral (H-1 NMR, C-13 NMR, and FT-IR) analysis, mass spectrometry and PM5 semiempirical methods. Estimation of the pharmacotherapeutic potential has been accomplished for the synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASSs). (C) 2011 Elsevier Ltd. All rights reserved.