(22R,23R,24S)-22,23-isopropylidenedioxy-24,25-dimethyl-5α-cholestane-2-en-6-one | 141069-87-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (22R,23R,24S)-22,23-isopropylidenedioxy-24,25-dimethyl-5α-cholestane-2-en-6-one
• CAS: 141069-87-6
• 化学式: C₃₂H₅₂O₃
• 分子量: 484.763
• InChiKey: IBMLLAXOAUKLHS-AFYVIKKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.83
• 重原子数：
  35.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (22R,23R,24S)-22,23-isopropylidenedioxy-24,25-dimethyl-5α-cholestane-2-en-6-one 在 盐酸 、 四氧化锇 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 水 、 叔丁醇 为溶剂， 反应 60.0h， 生成 25-methylcastasterone
  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：

  23,24-epoxy-(22R)-22-hydroxy-3α,6α-dimethoxymethyloxy-24,25-dimethyl-54b-cholestane 在 silica gel 、 copper(II) sulfate titanium(IV) isopropylate 、 重铬酸吡啶 、 锂硼氢 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 四氯乙烯 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 36.67h， 生成 (22R,23R,24S)-22,23-isopropylidenedioxy-24,25-dimethyl-5α-cholestane-2-en-6-one
  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