Acetic acid (1S,3R,9S,10R,13R,14R,17S)-3-acetoxy-17-ethyl-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl ester | 58702-10-6

• 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: Acetic acid (1S,3R,9S,10R,13R,14R,17S)-3-acetoxy-17-ethyl-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl ester
• 英文别名: [(1S,3R,9S,10R,13R,14R,17S)-1-acetyloxy-17-ethyl-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 58702-10-6
• 化学式: C₂₅H₃₆O₄
• 分子量: 400.558
• InChiKey: ZVZXCQLPBFOTGN-YSUBJHDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,3R,9S,10R,13R,14R,17S)-3-acetoxy-17-ethyl-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl ester 以 乙醚 为溶剂， 生成 Acetic acid (1S,5R)-5-acetoxy-3-[(Z)-2-((1S,3aR,7aR)-1-ethyl-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl)-vinyl]-2-methyl-cyclohex-2-enyl ester
  参考文献：
  名称：

  Structural analogs of lα,25-dihydroxycholecalciferol: Preparation and biologial assay of 1α-hydroxypregnacalciferol

  摘要：

  The synthesis of 1alpha-hydroxypregnacalciferol, a side chain analog of 1alpha,25-dihydroxycholecalciferol (1alpha,25-dihydroxyvitamin D3), is described. Pregnenolone acetate was converted in five steps to 5-pregnen-1alpha,3beta-diol. Conversion of the diol to pregna-5,7-diene-1alpha,3beta diol diacetate followed by ultraviolet irradiation gave the corresponding previtamin derivative. Thermal isomerization, hydrolysis and chromatography then furnished the desired analog, 1alpha-hydroxypregnacalciferol. The compound was tested in vivo for its effect on intestinal calcium transport, serum calcium and phosphate levels and bone calcification, and in vitro for its effect on bone resorption. When given to intact rats, either as a single dose or in repeated daily doses, the analog even at high dose levels, exhibited no biological activity. The compound stimulated bone resorption in vitro, but only at high concentrations.

  DOI：

  10.1016/0039-128x(75)90063-x
• 作为产物：
  描述：

  Acetic acid (1S,3R,8S,9S,10R,13R,14S,17S)-3-acetoxy-17-ethyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl ester 生成 Acetic acid (1S,3R,9S,10R,13R,14R,17S)-3-acetoxy-17-ethyl-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl ester
  参考文献：
  名称：

  Structural analogs of lα,25-dihydroxycholecalciferol: Preparation and biologial assay of 1α-hydroxypregnacalciferol

  摘要：

  The synthesis of 1alpha-hydroxypregnacalciferol, a side chain analog of 1alpha,25-dihydroxycholecalciferol (1alpha,25-dihydroxyvitamin D3), is described. Pregnenolone acetate was converted in five steps to 5-pregnen-1alpha,3beta-diol. Conversion of the diol to pregna-5,7-diene-1alpha,3beta diol diacetate followed by ultraviolet irradiation gave the corresponding previtamin derivative. Thermal isomerization, hydrolysis and chromatography then furnished the desired analog, 1alpha-hydroxypregnacalciferol. The compound was tested in vivo for its effect on intestinal calcium transport, serum calcium and phosphate levels and bone calcification, and in vitro for its effect on bone resorption. When given to intact rats, either as a single dose or in repeated daily doses, the analog even at high dose levels, exhibited no biological activity. The compound stimulated bone resorption in vitro, but only at high concentrations.

  DOI：

  10.1016/0039-128x(75)90063-x