methyl 22,23-didehydrohyodeoxycholate | 141069-90-1

• 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 22,23-didehydrohyodeoxycholate
• 英文别名: methyl (E,4R)-4-[(3R,5R,6S,8S,9S,10R,13R,14S,17R)-3,6-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pent-2-enoate
• CAS: 141069-90-1
• 化学式: C₂₅H₄₀O₄
• 分子量: 404.59
• InChiKey: CXMPGSVGJHPAAV-XCHHKWTISA-N

物化性质

• 沸点：
  516.1±25.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二甲醇缩甲醛 、 methyl 22,23-didehydrohyodeoxycholate 在 phosphorus pentoxide 作用下， 以 氯仿 为溶剂， 以87%的产率得到methyl 3α,6α-di(methoxymethyl)-22,23-dehydrohyodeoxycholate
  参考文献：
  名称：

  Studies on steroidal plant-growth regulator 25. Concise stereoselective construction of sidechain of brassinosteroid from the intact sidechain of hyodeoxycholic acid: formal syntheses of brassinolide, 25-methylbrassinolide, 26, 27-bisnorbrassinolide and their related compounds

  摘要：

  A concise stereoselective construction of sidechain of brassinolide (1), 25-methylbrassinolide (3) and 26,27-bisnorbrassinolide (4), which involves beta-alkylative 1,3- carbonyl transposition of the alpha,beta-unsaturated ketones 11 and 34 and alpha, beta-unsaturated methyl ester 26, using the intact sidechain of hyodeoxycholic acid (2) as starting material, is described. The formal syntheses of 1, 3 and 4 were accomplished. In the mean time, 25-methylcastasterone (21), 26,27-bisnortyphasterol (6) and the new 25-methyltyphasterol (5) were also syntehesized.

  DOI：

  10.1016/s0040-4020(01)88509-4
• 作为产物：
  描述：

  猪去氧胆酸 在 吡啶 、 苯亚硒酸 、 硫酸 、 硼酸 作用下， 以 四氢呋喃 、 甲醇 、 xylene 为溶剂， 反应 78.0h， 生成 methyl 22,23-didehydrohyodeoxycholate
  参考文献：
  名称：

  Studies on steroidal plant-growth regulator 25. Concise stereoselective construction of sidechain of brassinosteroid from the intact sidechain of hyodeoxycholic acid: formal syntheses of brassinolide, 25-methylbrassinolide, 26, 27-bisnorbrassinolide and their related compounds

  摘要：

  A concise stereoselective construction of sidechain of brassinolide (1), 25-methylbrassinolide (3) and 26,27-bisnorbrassinolide (4), which involves beta-alkylative 1,3- carbonyl transposition of the alpha,beta-unsaturated ketones 11 and 34 and alpha, beta-unsaturated methyl ester 26, using the intact sidechain of hyodeoxycholic acid (2) as starting material, is described. The formal syntheses of 1, 3 and 4 were accomplished. In the mean time, 25-methylcastasterone (21), 26,27-bisnortyphasterol (6) and the new 25-methyltyphasterol (5) were also syntehesized.

  DOI：

  10.1016/s0040-4020(01)88509-4