<3,4-13C2>methyl 5,20-bis(1',2'-ethylenedioxy)-3-oxo-4,5-secopregnane-2-carboxylate | 82938-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <3,4-13C2>methyl 5,20-bis(1',2'-ethylenedioxy)-3-oxo-4,5-secopregnane-2-carboxylate
• CAS: 82938-08-7
• 化学式: C₂₇H₄₂O₇
• 分子量: 480.604
• InChiKey: JGCJJGLURNLYJF-IUXQRDDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  <3,4-13C2>methyl 5,20-bis(1',2'-ethylenedioxy)-3-oxo-4,5-secopregnane-2-carboxylate 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 以49%的产率得到<3,4-13C2>-4-Pregnene-3,20-dione
  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：

  乙酰氯-13C2 、 methyl 5,20-bis(1',2'-ethylenedioxy)-4,5-seco-4-norpregnane-3-oate 在 lithium cyclohexylisopropylamide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以70%的产率得到<3,4-13C2>methyl 5,20-bis(1',2'-ethylenedioxy)-3-oxo-4,5-secopregnane-2-carboxylate
  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