6β-bromotestosterone acetate | 1458-93-1

• 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: 6β-bromotestosterone acetate
• 英文别名: 17β-acetoxy-6β-bromo-androst-4-en-3-one；17β-Acetoxy-6β-brom-androst-4-en-3-on；17β-Acetoxy-6β-bromo-4-androsten-3-on；6β-Brom-testosteron-acetat；[(6R,8R,9S,10R,13S,14S,17S)-6-bromo-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 1458-93-1
• 化学式: C₂₁H₂₉BrO₃
• 分子量: 409.363
• InChiKey: FKQTYBWZBKSBSR-UKSDXMLSSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  475.6±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6β-bromotestosterone acetate 在 2,4,6-三甲基吡啶 、 乙醚 、 溴 、 溶剂黄146 作用下， 生成 Estra-1,3,5(10),6-tetraene-3,17β-diol Diacetate
  参考文献：
  名称：

  Steroids. VII.¹ Contribution to the Bromination of ▵⁴-3-Ketosteroids and a New Partial Synthesis of the Natural Estrogens

  摘要：

  DOI：

  10.1021/ja01166a055
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢溴酸 、 溶剂黄146 作用下， 生成 6β-bromotestosterone acetate
  参考文献：
  名称：

  Inhoffen; Zuehlsdorff, Chemische Berichte, 1943, vol. 76, p. 233,238,245

  摘要：

  DOI：

文献信息

• Bile Acids and Steroids. XXVIII. Thiosteroids. (13). Further Study on Synthesis of 5'-Methylthieno-[4', 3', 2'-4, 5, 6]-5-en-3-one Steroids
  作者：Ken'ichi Takeda、Taichiro Komeno、Shoichi Ishihara

  DOI：10.1248/cpb.12.1433

  日期：——

  By treatment of potassium thiolacetate 6β-bromo-4-en-3-one steroids were converted to 6α-acetylthio-4-en-3-ones, which were further converted to 5'-methylthieno [4', 3', 2'-4, 5, 6]-5-en-3-ones by heating with sodium hydride in toluene

  经硫代乙酸钾处理后，6β-溴-4-烯-3-酮类固醇转化为 6α-乙酰硫基-4-烯-3-酮，在甲苯中用氢化钠加热，进一步转化为 5'-甲基噻吩基 [4'，3'，2'-4，5，6]-5-烯-3-酮
• Steroids and therapeutic compositions containing same
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：EP0133995A2

  公开（公告）日：1985-03-13

  Steroids of the formula and a therapeutic composition containing same which are useful as anti-cancer, anti-obesity, anti-hyperglycemic, anti-autoimmune and anti-hypercholesterolemic agents.

  式中的类固醇 以及含有这些物质的治疗组合物，可用作抗癌、抗肥胖、抗高血糖、抗自身免疫和抗高胆固醇血症的药物。
• The Reaction of Lead Tetraacetate with Progesterone and Testosterone
  作者：Robert L. Clarke、Konrad Dobriner、Aram Mooradian、Catherine M. Martini

  DOI：10.1021/ja01608a036

  日期：1955.2.1
• Synthesis and some reactions of 6-bromoandrogens: Potential affinity ligand and inactivator of estrogen synthetase
  作者：Mitsuteru Numazawa、Yoshio Osawa

  DOI：10.1016/0039-128x(79)90085-0

  日期：1979.9

  The synthesis of epimeric 6-bromo-4-androstene-3,17-dione (1a and 1b), 6-bromotestosterone (2a and 2b) and its acetate (3a and 3b), and 6-bromo-16 alpha-acetoxy-4-androstene-3,17-dione (5a and 5b), and 6 beta-bromo-16 alpha-hydroxy-4-androstene-3,17-dione (4) is described. The interconversions among compounds 1, 2, and 3 are also studied. The 6 beta-isomer (1b, 2b, and 3b) was epimerized to the 6 alpha-isomer (1a, 2a and 3a) in carbon tetrachloride or chloroform-methanol (9:1) and the 6 alpha-isomer was isolated by fractional crystallization from the epimeric mixture. 6 alpha-Bromo isomer 1a was also epimerized back to 6 beta-bromo isomer 1b in chloroform-methanol (9:1). Two polymorphic forms of 6 beta-bromotestosterone acetate (3b) were isolated (mp. 114--117 degrees and 138--141 degrees). The 6 beta-bromo isomers were found to be unstable in methanol and decomposed to give 5 alpha-androstane-3,6-dione derivative (6). The results of irreversible inactivation of human placental androgen aromatase with some of these 6-bromoandrogens are discussed.
• Einwirkung von N-Brom-succinimid aufΔ 4-3-Keto-steroide
  作者：Ch Meystre、A. Wettstein

  DOI：10.1007/bf02154217

  日期：1946.10