2-methylenecholest-4-en-3-one | 127063-81-4

• 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: 2-methylenecholest-4-en-3-one
• 英文别名: (8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2-methylidene-6,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 127063-81-4
• 化学式: C₂₈H₄₄O
• 分子量: 396.657
• InChiKey: PSAHUPIUUNHIME-RANCRSHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.76
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-methylenecholest-4-en-3-one 在 正丁基锂 、 三甲基氯硅烷 、 sodium hydride 、 sodium iodide 作用下， 以 正己烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 8.25h， 生成 methyl 6-(3-oxocholest-4-en-2α-yl)-4-thiahexanoate
  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 聚合甲醛 、 potassium carbonate 作用下， 生成 2-methylenecholest-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

• Desai, Umesh R.; Trivedi, Girish K., Liebigs Annalen der Chemie, 1990, # 7, p. 711 - 712
  作者：Desai, Umesh R.、Trivedi, Girish K.

  DOI：——

  日期：——
• DESAI, UMESH R.;TRIVEDI, GIRISH K., LIEBIGS ANN. CHEM.,(1990) N, C. 711-712
  作者：DESAI, UMESH R.、TRIVEDI, GIRISH K.

  DOI：——

  日期：——