3β-acetoxycholest-5-ene-16,22-dione | 649723-72-8

• 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: 3β-acetoxycholest-5-ene-16,22-dione
• 英文别名: 3β-O-acetylcholest-5-ene-16,22-dione；[(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-16-oxo-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 649723-72-8
• 化学式: C₂₉H₄₄O₄
• 分子量: 456.666
• InChiKey: UXLUAPFFKNHMDU-WUVNXUQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxycholest-5-ene-16,22-dione 在 吡啶 、 咪唑 、 sodium tetrahydroborate 、 高氯酸 、 4-甲基苯磺酸吡啶 、 乙酸酐 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 39.0h， 生成 (22R)-3β,16β-diacetoxycholesta-5,17(20)-diene-22-ol
  参考文献：
  名称：

  A Novel Synthetic Approach from Diosgenin to a 17α‐Hydroxy Orthoester via a Regio‐ and Stereo‐Specific Rearrangement of an Epoxy Ester

  摘要：

  A cholesterol model compound, containing 16beta-acetoxy, 17alpha-hydroxy, and (20S, 22R)-epoxy groups was synthesized from diosgenin in 13 steps and was rearranged regio- and stereo-specifically to an orthoester with BF3.Et2O.

  DOI：

  10.1081/scc-120028627
• 作为产物：
  描述：

  (22β)-3β-hydroxyfurost-5-ene 在 吡啶 、 potassium dichromate 、 溶剂黄146 作用下， 反应 24.0h， 生成 3β-acetoxycholest-5-ene-16,22-dione
  参考文献：
  名称：

  A Novel Synthetic Approach from Diosgenin to a 17α‐Hydroxy Orthoester via a Regio‐ and Stereo‐Specific Rearrangement of an Epoxy Ester

  摘要：

  A cholesterol model compound, containing 16beta-acetoxy, 17alpha-hydroxy, and (20S, 22R)-epoxy groups was synthesized from diosgenin in 13 steps and was rearranged regio- and stereo-specifically to an orthoester with BF3.Et2O.

  DOI：

  10.1081/scc-120028627

文献信息

• Synthesis and structure of 16,22-diketocholesterol bound to oxysterol-binding protein Osh4
  作者：Myong Chul Koag、Young Cheun、Yi Kou、Hala Ouzon-Shubeita、Kyungjin Min、Arthur F. Monzingo、Seongmin Lee

  DOI：10.1016/j.steroids.2013.05.016

  日期：2013.9

  We have synthesized 16,22-diketocholesterol, a novel ligand for oxysterol-binding protein Osh4, and determined X-ray structure of the diketocholesterol in complex with Osh4. The X-ray structure shows that alpha 7 helix of Osh4 assumes open conformation while the rest of Osh4, closed conformation, implying this diketocholesterol-bound Osh4 structure may represent a structural intermediate between the two conformations. (C) 2013 Elsevier Inc. All rights reserved.