methyl 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oate | 712266-08-5

• 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: methyl 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oate
• 英文别名: methyl 3,3-bis(1H-pyrrol-2-yl)-5β-cholan-24-oate；methyl (4R)-4-[(5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,3-bis(1H-pyrrol-2-yl)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 712266-08-5
• 化学式: C₃₃H₄₈N₂O₂
• 分子量: 504.756
• InChiKey: PDFKYBWKWRTGKS-MHDRVXATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  57.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2'-(2,2-丙烷二基)二(1H-吡咯) 、 丙酮 、 methyl 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oate 在 三氟乙酸 作用下， 反应 1.5h， 以24%的产率得到methyl (4R)-4-[(5R,8R,9S,10S,13R,14S,17R)-5',5',10,10',10',13,20',20'-octamethylspiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,15'-21,22,23,24-tetrahydroporphyrin]-17-yl]pentanoate
  参考文献：
  名称：

  Synthesis of spiroannulated oligopyrrole macrocycles derived from lithocholic acid

  摘要：

  Two new steroidal spiroannulated calix[4]pyrroles 5 and 10, derived from bile acids (lithocholate), were prepared by the acid catalyzed condensation of methyl-3,3-bis(pyrrol-2-yl)-5 beta-cholan-24-oate 3 with carbonyl Compounds and with 2.2'-propane-2,2-diylbis(1H-pyrrole), respectively. The new compounds were fully characterized by physicochemical methods. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.04.004
• 作为产物：
  描述：

  3-Alpha-羟基-5-beta-24-胆烷酸甲酯 在 Na₂CrO₇*2H₂O 、 三氟化硼乙醚 作用下， 反应 6.0h， 生成 methyl 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oate
  参考文献：
  名称：

  Synthesis and characterization of lithocholic acid derived dipyrromethanes: precursors for pyrrole-steroidal macrocycles

  摘要：

  Three steroidal dipyrromethanes, 3,3,24,24-tetrakis(pyrrol-2-yl)-5beta-cholane 1, 3,3-bis(pyrrol-2-yl)-5beta-cholan-24-oic acid 2, and methyl 3,3-bis(pyrrol-2-yl)-5beta-cholan-24-oate 3, have been prepared from 3alpha-hydroxy-5beta-cholan-24-oic acid (lithocholic acid) 4 in good overall yields. The structures of 1-3 have been fully characterized by H-1, C-13, PFG DQF H-1-H-1 COSY, H-1-H-1 ROESY, C-13 DEPT-135, PFG H-1-C-13 HMQC, PFG H-1-C-13 HMBC, and PFG H-1-N-15 HMBC NMR spectra. Their molecular weights and compositions have been determined by ESI-TOF and El mass spectra, and elemental analyses. The energetically optimised geometry and isotropic 13 C NMR chemical shifts of 3,3,24,24-tetrakis(pyffol-2-yl)-5beta-cholane 1 have been calculated by ab initio HF/6-31G* and DFT B3PW91/6-311G* methods. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2004.02.014