(13S,17R)-17-hydroxy-13,14-seco-androst-4-en-3-one | 775355-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (13S,17R)-17-hydroxy-13,14-seco-androst-4-en-3-one
• 英文别名: (1S,2R,10R,14R,15S)-14-hydroxy-2,15-dimethyltricyclo[8.7.0.02,7]heptadec-6-en-5-one
• CAS: 775355-70-9
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: GZUPYIUQUYPXAV-ITOHMHRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  (13S,17R)-17-hydroxy-13,14-seco-androst-4-en-3-one 在 chromium(VI) oxide 作用下， 以 吡啶 为溶剂， 以88%的产率得到(13S)-13,14-seco-androst-4-en-3,17-dione
  参考文献：
  名称：

  Synthesis of 13,14-secotestosterone derivatives

  摘要：

  A number of testosterone analogs with a 13,14-secosteroidal fragment have been prepared from (13S)-13-iodo-6beta-methoxy-3alpha, 5-cyclo-13,14-seco-5alpha-androstan-14,17-dione. The key steps involved stereoselective deiodination of the starting compound with triphenylphosphine and selective protection of the 17-keto group with trimethylsilylcyanide. Removal of iodine at C-13 proceeded with inversion of the configuration at C-13, which has been established by X-ray crystallography. 13,14-Secotestosterone analogues substituted and non-substituted at C-14 have been prepared. The obtained compounds containing flexible CD ring fragments are of great interest for comparative studies in biological tests together with testosterone and other steroids with a rigid tetracyclic skeleton. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.04.010
• 作为产物：
  描述：

  (13S)-13-iodo-6β-methoxy-3α,5-cyclo-13,14-seco-5α-androstane-14,17-dione 在 Pd-BaSO₄ 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 氯化亚砜 、 四丁基氟化铵 、 氢气 、 aluminum isopropoxide 、 L-Selectride 、 对甲苯磺酸 、 三苯基膦 、 calcium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 环己酮 、 甲苯 为溶剂， 反应 35.33h， 生成 (13S,17R)-17-hydroxy-13,14-seco-androst-4-en-3-one
  参考文献：
  名称：

  Synthesis of 13,14-secotestosterone derivatives

  摘要：

  A number of testosterone analogs with a 13,14-secosteroidal fragment have been prepared from (13S)-13-iodo-6beta-methoxy-3alpha, 5-cyclo-13,14-seco-5alpha-androstan-14,17-dione. The key steps involved stereoselective deiodination of the starting compound with triphenylphosphine and selective protection of the 17-keto group with trimethylsilylcyanide. Removal of iodine at C-13 proceeded with inversion of the configuration at C-13, which has been established by X-ray crystallography. 13,14-Secotestosterone analogues substituted and non-substituted at C-14 have been prepared. The obtained compounds containing flexible CD ring fragments are of great interest for comparative studies in biological tests together with testosterone and other steroids with a rigid tetracyclic skeleton. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.04.010