2α-(2'-hydroxyethyl)cholest-4-en-3-one | 134329-93-4

• 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: 2α-(2'-hydroxyethyl)cholest-4-en-3-one
• 英文别名: (2S,8S,9S,10R,13R,14S,17R)-2-(2-hydroxyethyl)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 134329-93-4
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: LLVJAGAVIOFTIY-SQONKTMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丁二酸酐 、 2α-(2'-hydroxyethyl)cholest-4-en-3-one 在 吡啶 、 咪唑 作用下， 反应 5.0h， 以43%的产率得到4-[2-[(2S,8S,9S,10R,13R,14S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-3-氧代-1,2,6,7,8,9,11,12,14,15,16,17-十二氢环戊烯并[a]菲-2-基]乙氧基]-4-氧代丁酸
  参考文献：
  名称：

  New steroid haptens for radioimmunoassay: Synthesis of steroids substituted with thioether or ester linkages at the 2α-position

  摘要：

  Haptens with bridge at the 2-position have not yet been explored. Radioimmunoassays with antibodies directed against 2-alpha-alkyl bridged steroid haptens are expected to be highly specific due to greater topographical exposure and similarity in conformation to the native steroid. The 2-alpha-alkyl bridged haptens were synthesized by first adding a cyclopropane ring to 2-methylene-4-en-3-one. Selective opening of the three-membered ring with trimethyl silyl iodide and transformation of the iodo group gave a carbocyclic acid, the desired analog for conjugation with protein.

  DOI：

  10.1016/0039-128x(91)90080-f
• 作为产物：
  描述：

  2-(ethoxycarbonyl hydroxymethylene)cholest-4-en-3-one 在 sodium hydroxide 、 聚合甲醛 、 三甲基氯硅烷 、 sodium hydride 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 18.75h， 生成 2α-(2'-hydroxyethyl)cholest-4-en-3-one
  参考文献：
  名称：

  New steroid haptens for radioimmunoassay: Synthesis of steroids substituted with thioether or ester linkages at the 2α-position

  摘要：

  Haptens with bridge at the 2-position have not yet been explored. Radioimmunoassays with antibodies directed against 2-alpha-alkyl bridged steroid haptens are expected to be highly specific due to greater topographical exposure and similarity in conformation to the native steroid. The 2-alpha-alkyl bridged haptens were synthesized by first adding a cyclopropane ring to 2-methylene-4-en-3-one. Selective opening of the three-membered ring with trimethyl silyl iodide and transformation of the iodo group gave a carbocyclic acid, the desired analog for conjugation with protein.

  DOI：

  10.1016/0039-128x(91)90080-f

文献信息

• New steroid haptens for radioimmunoassay: Synthesis of steroids substituted with thioether or ester linkages at the 2α-position
  作者：Umesh R. Desai、Girish K. Trivedi

  DOI：10.1016/0039-128x(91)90080-f

  日期：1991.4

  Haptens with bridge at the 2-position have not yet been explored. Radioimmunoassays with antibodies directed against 2-alpha-alkyl bridged steroid haptens are expected to be highly specific due to greater topographical exposure and similarity in conformation to the native steroid. The 2-alpha-alkyl bridged haptens were synthesized by first adding a cyclopropane ring to 2-methylene-4-en-3-one. Selective opening of the three-membered ring with trimethyl silyl iodide and transformation of the iodo group gave a carbocyclic acid, the desired analog for conjugation with protein.