(20'R)-2-[de-A,B-18',20'-epoxy-25'-hydroxy-21'-norcholest-8'-ylidene]-hydrazinecarboxamide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (20'R)-2-[de-A,B-18',20'-epoxy-25'-hydroxy-21'-norcholest-8'-ylidene]-hydrazinecarboxamide
• 英文别名: [(E)-[(3R,3aS,5aR,9aR)-3-(4-hydroxy-4-methylpentyl)-3,3a,4,5,5a,7,8,9-octahydro-1H-indeno[1,7a-c]furan-6-ylidene]amino]urea
• 化学式: C₁₈H₃₁N₃O₃
• 分子量: 337.462
• InChiKey: YDKANPCKZMTWDC-ARPVILPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (8β)-(20R)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-18,20-epoxy-21-norcholestan-25-ol 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 AG(R) 50W-X₄ resin 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 (20'R)-2-[de-A,B-18',20'-epoxy-25'-hydroxy-21'-norcholest-8'-ylidene]-hydrazinecarboxamide
  参考文献：
  名称：

  Synthesis of New 18-Substituted Analogues of Calcitriol Using a Photochemical Remote Functionalization

  摘要：

  A novel convergent synthetic approach to new analogues of calcitriol modified at the C-18 position is reported. The key step in the synthesis is the 20-hydroxyl-directed photochemical iodination of the 18-methyl group in the presence of (diacetoxyiodo)benzene. Using this methodology, two new analogues of calcitriol were prepared: the first contains a hydroxylated alkyl side chain attached at C-18 with the natural side chain replaced by an isopropylidene group; the second is a conformationally locked analogue due to an extra oxacycle between the C-18 and C-20 positions.

  DOI：

  10.1021/jo020022z

文献信息

• Synthesis of New 18-Substituted Analogues of Calcitriol Using a Photochemical Remote Functionalization
  作者：Iván Cornella、José Pérez Sestelo、Antonio Mouriño、Luis A. Sarandeses

  DOI：10.1021/jo020022z

  日期：2002.7.1

  A novel convergent synthetic approach to new analogues of calcitriol modified at the C-18 position is reported. The key step in the synthesis is the 20-hydroxyl-directed photochemical iodination of the 18-methyl group in the presence of (diacetoxyiodo)benzene. Using this methodology, two new analogues of calcitriol were prepared: the first contains a hydroxylated alkyl side chain attached at C-18 with the natural side chain replaced by an isopropylidene group; the second is a conformationally locked analogue due to an extra oxacycle between the C-18 and C-20 positions.