methyl 3α-(ethoxycarbonyloxy)-7α-(4-pentenoyloxyl)-5β-cholanoate | 1115381-90-2

• 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-(ethoxycarbonyloxy)-7α-(4-pentenoyloxyl)-5β-cholanoate
• 英文别名: methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3-ethoxycarbonyloxy-10,13-dimethyl-7-pent-4-enoyloxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 1115381-90-2
• 化学式: C₃₃H₅₂O₇
• 分子量: 560.772
• InChiKey: CTNJQWRFCLHYTP-MGGGQBTCSA-N

物化性质

• 沸点：
  600.4±38.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3α-(ethoxycarbonyloxy)-7α-(4-pentenoyloxyl)-5β-cholanoate 在 potassium carbonate 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.0h， 以95%的产率得到3α-(hydroxyl)-7α-(4-pentenoyloxyl)-5β-cholanoic acid
  参考文献：
  名称：

  Synthesis and comparative spectroscopic analysis of two chenodeoxycholic acid (CDCA) derivatives with closely related 7α-ester moieties

  摘要：

  3 alpha-Hydroxyl-7 alpha-(4-pentenoyloxy)-5 beta-cholanoic acid (5) has been synthesized in four step reactions starting from CDCA. The serendipitous synthesis of methyl 3 alpha-(allyloxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate (7) has led us to compare the spectroscopic difference of the 7 alpha-(allyloxycarbonyloxy)group versus the 7 alpha-(4-pentenoyloxy) group. The molecular Structures of these compounds were confirmed by X-ray Crystallography. Methyl 3 alpha-(ethoxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate was obtained by a method, which may prove useful in the synthesis of C-14-labeled derivatives for metabolic studies. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.052
• 作为产物：
  描述：

  4-戊烯酸 、 (3alpha,5beta,7alpha)-3-[(乙氧羰基)氧基]-7-羟基胆烷-24-酸甲酯 在 三乙胺 、 2,6-二氯苯甲酰氯 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以94%的产率得到methyl 3α-(ethoxycarbonyloxy)-7α-(4-pentenoyloxyl)-5β-cholanoate
  参考文献：
  名称：

  Synthesis and comparative spectroscopic analysis of two chenodeoxycholic acid (CDCA) derivatives with closely related 7α-ester moieties

  摘要：

  3 alpha-Hydroxyl-7 alpha-(4-pentenoyloxy)-5 beta-cholanoic acid (5) has been synthesized in four step reactions starting from CDCA. The serendipitous synthesis of methyl 3 alpha-(allyloxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate (7) has led us to compare the spectroscopic difference of the 7 alpha-(allyloxycarbonyloxy)group versus the 7 alpha-(4-pentenoyloxy) group. The molecular Structures of these compounds were confirmed by X-ray Crystallography. Methyl 3 alpha-(ethoxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate was obtained by a method, which may prove useful in the synthesis of C-14-labeled derivatives for metabolic studies. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.11.052

文献信息

• Synthesis and comparative spectroscopic analysis of two chenodeoxycholic acid (CDCA) derivatives with closely related 7α-ester moieties
  作者：Xinyan Bai、Charles Barnes、Jerry Ray Dias

  DOI：10.1016/j.tetlet.2008.11.052

  日期：2009.2

  3 alpha-Hydroxyl-7 alpha-(4-pentenoyloxy)-5 beta-cholanoic acid (5) has been synthesized in four step reactions starting from CDCA. The serendipitous synthesis of methyl 3 alpha-(allyloxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate (7) has led us to compare the spectroscopic difference of the 7 alpha-(allyloxycarbonyloxy)group versus the 7 alpha-(4-pentenoyloxy) group. The molecular Structures of these compounds were confirmed by X-ray Crystallography. Methyl 3 alpha-(ethoxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate was obtained by a method, which may prove useful in the synthesis of C-14-labeled derivatives for metabolic studies. (c) 2008 Elsevier Ltd. All rights reserved.