PRI-2168 | 135604-70-5

• 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: PRI-2168
• 英文别名: (24E)-1alpha,25-dihydroxy-24,24a-didehydro-24a,24b-dihomovitamin D3/(24E)-1alpha,25-dihydroxy-24,24a-didehydro-24a,24b-dihomocholecalciferol；(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R)-8-hydroxy-8-methylnon-5-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• CAS: 135604-70-5
• 化学式: C₂₉H₄₆O₃
• 分子量: 442.682
• InChiKey: OOFQCOJQWBYMNI-KPDJITMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-4-苯基硫基-2-丁醇 在 咪唑 、 disodium hydrogenphosphate 、 sodium amalgam 、 正丁基锂 、 1,10-菲罗啉 、 四丁基氟化铵 、 二异丙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 PRI-2168
  参考文献：
  名称：

  Synthesis of side-chain homologated analogs of 1,25-dihydroxycholecalciferol and 1,25-dihydroxyergocalciferol

  摘要：

  A novel synthesis of side-chain homologated analogs of vitamin D isomers has been described. The synthesis allows for the insertion of the double bond into the C-24 position of the side chain. The key synthetic step involves the coupling of a new C24-vitamin D synthon with the respective side-chain fragment. The method is illustrated by the preparation of (24E)-24,24a-dehydro-24,24-dihomo-1,25-dihydroxycholecalciferol (1) and (24b R)- and (24b S)-24,24-dihomo-1,25-dihydroxyergocalciferols (2 and 3). Trans geometry of the newly formed double bond in the side chain was confirmed by high field nuclear magnetic resonance spectra.

  DOI：

  10.1016/0039-128x(91)90052-w

文献信息

• Synthesis of side-chain homologated analogs of 1,25-dihydroxycholecalciferol and 1,25-dihydroxyergocalciferol
  作者：M CHODYNSKI、A KUTNER

  DOI：10.1016/0039-128x(91)90052-w

  日期：1991.6

  A novel synthesis of side-chain homologated analogs of vitamin D isomers has been described. The synthesis allows for the insertion of the double bond into the C-24 position of the side chain. The key synthetic step involves the coupling of a new C24-vitamin D synthon with the respective side-chain fragment. The method is illustrated by the preparation of (24E)-24,24a-dehydro-24,24-dihomo-1,25-dihydroxycholecalciferol (1) and (24b R)- and (24b S)-24,24-dihomo-1,25-dihydroxyergocalciferols (2 and 3). Trans geometry of the newly formed double bond in the side chain was confirmed by high field nuclear magnetic resonance spectra.