苯丁酸,b-氨基-2,4-二氯-,盐酸(1:1),(bR)- | 88663-11-0

• 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
• 中文名称: 苯丁酸,b-氨基-2,4-二氯-,盐酸(1:1),(bR)-
• 英文名称: D-(-)-norgestrel 17β-cyclopentanecarboxylate
• 英文别名: levonorgestrel cyclopentylcarboxylate
• CAS: 88663-11-0
• 化学式: C₂₇H₃₆O₃
• 分子量: 408.581
• InChiKey: UAXDSIPJLFCFKW-WOSSHHRXSA-N

物化性质

• 沸点：
  525.3±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  苯丁酸,b-氨基-2,4-二氯-,盐酸(1:1),(bR)- 在 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 作用下， 以 吡啶 、 乙醇 、 水 、 溶剂黄146 、 丙酮 、 苯 为溶剂， 反应 3.25h， 生成 6ξ-bromonorgestrel 17β-cyclopentanecarboxylate
  参考文献：
  名称：

  Development and use of a radioimmunoassay for D-(-)-norgestrel 17β-cyclopentane-carboxylate

  摘要：

  The synthesis of the 6 alpha-carboxymethylmercapto BSA and homologous histamine conjugate of D-(-)-norgestrel 17 beta-cyclopentanecarboxylate is reported. Using the BSA conjugate as an immunogen for the development of antibody in the rabbit and the 125I-histamine conjugate as the radioligand, a radioimmunoassay (RIA) for the ester was developed. Serum profiles of the free alcohol and ester were determined following IV or IM injection in macaques. Peak values for the ester (about 12 ng/mL) were observed 2 min following an IV bolus of 0.5 mg in one rhesus monkey. Blood levels dropped rapidly within the first 30 min and were barely detectable at 24 h. Serum levels of the free alcohol rose to a peak at 30 min and then declined slowly to very low values by 24 h. Following IM injection of 20 mg in cynomolgus monkeys, peak levels of the ester were observed within a few days while the free alcohol reached a maximum about day 30. Serum concentrations of D-(-)-norgestrel had fallen to about 0.4 ng/mL 160 days post-injection when levels of the ester fell below 0.2 ng/mL.

  DOI：

  10.1016/0039-128x(86)90039-5
• 作为产物：
  描述：

  环戊基甲酰氯 、 左炔诺孕酮 在 thallium (I) ethoxide 作用下， 生成 苯丁酸,b-氨基-2,4-二氯-,盐酸(1:1),(bR)-
  参考文献：
  名称：

  Long-acting contraceptive agents: Design of the who chemical synthesis programme

  摘要：

  The great demand for improved long-acting injectable steroid contraceptives, particularly in developing countries, and the relative lack of interest from the pharmaceutical industry to develop such products stimulated WHO to launch a synthetic and screening programme to find improved, safe and acceptable injectable preparations. More than 210 esters of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) and levonorgestrel (D-(-)-13 beta-ethyl-17 alpha-ethynyl-17 beta-hydroxygon-4-en-3-one) have been prepared in university-based research laboratories situated mainly in developing countries, and then screened by NICHHD in animal models. The following three compounds, levonorgestrel butanoate, cyclopropylcarboxylate and cyclobutylcarboxylate, proved to be particularly long-acting when administered as microcrystalline suspensions. The overall strategy of this research and development programme is described.

  DOI：

  10.1016/0039-128x(83)90095-8

文献信息

• Norethisterone and levonorgestrel esters: A novel synthetic method
  作者：S.L. Leung、R. Karunanithy、G. Becket、S.H. Yeo

  DOI：10.1016/0039-128x(85)90027-3

  日期：1985.7

  Aliphatic, alicyclic and arylcarboxylic esters of norethisterone and levonorgestrel were prepared in a one-step synthesis and in near-quantitative yield using trifluoroacetic anhydride.