17β-benzoyloxy-5-oxo-3,5-seco-A-nor-estran-3-oic acid | 122426-44-2

• 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: 17β-benzoyloxy-5-oxo-3,5-seco-A-nor-estran-3-oic acid
• 英文别名: 17β-Benzoyloxy-5-oxo-3,5-seco-A-nor-oestran-3-saeure；(3S,3aS,5aS,6R,9aR,9bS)-3-(Benzoyloxy)dodecahydro-3a-methyl-7-oxo-1H-benz[e]indene-6-propanoic Acid；3-[(3S,3aS,5aS,6R,9aR,9bS)-3-benzoyloxy-3a-methyl-7-oxo-2,3,4,5,5a,6,8,9,9a,9b-decahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid
• CAS: 122426-44-2
• 化学式: C₂₄H₃₀O₅
• 分子量: 398.499
• InChiKey: AAUPTDDOIJHZKP-IGRZAPSXSA-N

物化性质

• 沸点：
  564.1±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  0.62
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  17β-benzoyloxy-5-oxo-3,5-seco-A-nor-estran-3-oic acid 在 高氯酸 、 乙酸酐 作用下， 以 乙酸乙酯 为溶剂， 生成 3-oxo-4-oxa-5(10)-estren-17β-yl benzoate
  参考文献：
  名称：

  Synthesis of 3,4-13C2 steroids

  摘要：

  A-ring enollactones la, lb, or 9 derived from 4-cholesten-3-one, testosterone benzoate or 3-oxo-4-estren-17 beta-yl benzoate were condensed with [1,2-13C2]acetyl chloride to give intermediates 2a, 2b, or 10. 2a and 2b were cyclized by acid or base to give 3,4 13c-labeled 4-cholesten-3-one and testosterone, respectively. [3,4-13c2 14-Cholesten-3-one was converted via reduction of its trimethylsilyl enol ether to [3,4-13C2] cholesterol. Acetyl enollactone 10 was cyclized in acetic acid to [3,4-13c2] 3-oxo-4-estren-17beta-yl benzoate followed by aromatization and hydrolysis to produce ]3,4-13c2] estradiol-17 beta. Alternatively, cyclization of 10 with base afforded [3,4-13c2-oxo-4-estren-17 beta-ol directly, which was then oxidized and aromatized to yield ]3,4-13c2] estrone. Ozonolysis of progesterone, conversion to the diketal ester 16 and acylation followed by acid hydrolysis furnished [3,4-13c2] progesterone.

  DOI：

  10.1016/0039-128x(82)90147-7
• 作为产物：
  描述：

  nandrolone benzoate 在 臭氧 作用下， 生成 17β-benzoyloxy-5-oxo-3,5-seco-A-nor-estran-3-oic acid
  参考文献：
  名称：

  Synthesis of 3,4-13C2 steroids

  摘要：

  A-ring enollactones la, lb, or 9 derived from 4-cholesten-3-one, testosterone benzoate or 3-oxo-4-estren-17 beta-yl benzoate were condensed with [1,2-13C2]acetyl chloride to give intermediates 2a, 2b, or 10. 2a and 2b were cyclized by acid or base to give 3,4 13c-labeled 4-cholesten-3-one and testosterone, respectively. [3,4-13c2 14-Cholesten-3-one was converted via reduction of its trimethylsilyl enol ether to [3,4-13C2] cholesterol. Acetyl enollactone 10 was cyclized in acetic acid to [3,4-13c2] 3-oxo-4-estren-17beta-yl benzoate followed by aromatization and hydrolysis to produce ]3,4-13c2] estradiol-17 beta. Alternatively, cyclization of 10 with base afforded [3,4-13c2-oxo-4-estren-17 beta-ol directly, which was then oxidized and aromatized to yield ]3,4-13c2] estrone. Ozonolysis of progesterone, conversion to the diketal ester 16 and acylation followed by acid hydrolysis furnished [3,4-13c2] progesterone.

  DOI：

  10.1016/0039-128x(82)90147-7

文献信息

• The Partial Degradation and Reconstitution of the “A” Ring of Estradiol¹
  作者：John A. Hartman、Arthur J. Tomasewski、Andre S. Dreiding

  DOI：10.1021/ja01602a054

  日期：1956.11
• Birch, Chemistry and Industry, 1951, p. 616
  作者：Birch

  DOI：——

  日期：——