(8R,9S,10R,13S,14S,16R)-10,13-dimethyl-16-(phenylselanyl)-1,4,7,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17(2H)-one | 74137-05-6

• 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: (8R,9S,10R,13S,14S,16R)-10,13-dimethyl-16-(phenylselanyl)-1,4,7,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17(2H)-one
• CAS: 74137-05-6
• 化学式: C₂₇H₃₄O₃Se
• 分子量: 485.525
• InChiKey: CNVPKWOGWOISSB-AHXXJLMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (8R,9S,10R,13S,14S,16R)-10,13-dimethyl-16-(phenylselanyl)-1,4,7,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17(2H)-one 在 lithium aluminium tetrahydride 、 三苯基氢化锡 、 对甲苯磺酸 作用下， 以 乙醚 、 丙酮 、 甲苯 为溶剂， 反应 6.0h， 生成 睾酮
  参考文献：
  名称：

  Synthesis and biochemical screening of phenylselenium-substituted steroid hormones

  摘要：

  The syntheses of phenylselenium-substituted progesterone [21- (1) and 17 alpha-(phenylseleno)progesterone (2)] and testosterone [16 beta- (3) and 16 alpha-(phenylseleno)testosterone (4)] derivatives are described, along with data which help to establish the stereochemistry of the substituents in the testosterone molecules. Except for 21-(phenylseleno)-progesterone, the molecules exhibit greatly reduced receptor-binding capabilities.

  DOI：

  10.1021/jm00181a004
• 作为产物：
  描述：

  3,3-(ethylenedioxy)-5-androsten-17β-ol 在 正丁基锂 、 dipyridine chromium trioxide 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.25h， 生成 (8R,9S,10R,13S,14S,16R)-10,13-dimethyl-16-(phenylselanyl)-1,4,7,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17(2H)-one
  参考文献：
  名称：

  Synthesis and biochemical screening of phenylselenium-substituted steroid hormones

  摘要：

  The syntheses of phenylselenium-substituted progesterone [21- (1) and 17 alpha-(phenylseleno)progesterone (2)] and testosterone [16 beta- (3) and 16 alpha-(phenylseleno)testosterone (4)] derivatives are described, along with data which help to establish the stereochemistry of the substituents in the testosterone molecules. Except for 21-(phenylseleno)-progesterone, the molecules exhibit greatly reduced receptor-binding capabilities.

  DOI：

  10.1021/jm00181a004