1,2,4,16α,16β-pentadeuterioestrone

• 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: 1,2,4,16α,16β-pentadeuterioestrone
• 英文别名: estrone-1,2,4,16α,16β-d5；(8R,9S,13S,14S)-1,2,4,16,16-pentadeuterio-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-one
• 化学式: C₁₈H₂₂O₂
• 分子量: 275.332
• InChiKey: DNXHEGUUPJUMQT-BDPQCXOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  1,2,4,16α,16β-pentadeuterioestrone 在 水 、 三氟乙酸 作用下， 反应 20.0h， 以84%的产率得到1,16α,16β-trideuterioestrone
  参考文献：
  名称：

  Regioselective deuterium labeling of estrone and catechol estrogen metabolites

  摘要：

  Increased exposure to estrogens and estrogen metabolites is linked with increased rates of breast, ovarian and other human cancers. Metabolism of estrogen can led to formation of electrophilic o-quinones capable of binding to DNA In order to gain insight into the mechanism of estrogen-induced DNA damage, estrone and catechol estrogens derived from estrone, have been regioselectively labeled with deuterium at the 1-position. Estrone-1-d, estrone-1,2,4-d(3), 4-hydroxyestrone-1-d and 2-hydroxyestrone-1-d have been synthesized with or without deuteriums at the 16-position. The key labeling step involves deuterated trifluoroacetic acid exchange catalyzed by t-butyl alcohol. This economical, straightforward labeling technique makes available a range of estrone compounds containing deuterium at the 1-position. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.08.018
• 作为产物：
  描述：

  雌酚酮 在 三氟化硼乙醚 、 重水 、 magnesium sulfate 、 三氟乙酸酐 作用下， 反应 20.5h， 生成 1,2,4,16α,16β-pentadeuterioestrone
  参考文献：
  名称：

  Regioselective deuterium labeling of estrone and catechol estrogen metabolites

  摘要：

  Increased exposure to estrogens and estrogen metabolites is linked with increased rates of breast, ovarian and other human cancers. Metabolism of estrogen can led to formation of electrophilic o-quinones capable of binding to DNA In order to gain insight into the mechanism of estrogen-induced DNA damage, estrone and catechol estrogens derived from estrone, have been regioselectively labeled with deuterium at the 1-position. Estrone-1-d, estrone-1,2,4-d(3), 4-hydroxyestrone-1-d and 2-hydroxyestrone-1-d have been synthesized with or without deuteriums at the 16-position. The key labeling step involves deuterated trifluoroacetic acid exchange catalyzed by t-butyl alcohol. This economical, straightforward labeling technique makes available a range of estrone compounds containing deuterium at the 1-position. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.08.018

文献信息

• Regioselective deuterium labeling of estrone and catechol estrogen metabolites
  作者：Douglas E. Stack、Justin Ritonya、Scott Jakopovic、Brittney Maloley-Lewis

  DOI：10.1016/j.steroids.2014.08.018

  日期：2014.12

  Increased exposure to estrogens and estrogen metabolites is linked with increased rates of breast, ovarian and other human cancers. Metabolism of estrogen can led to formation of electrophilic o-quinones capable of binding to DNA In order to gain insight into the mechanism of estrogen-induced DNA damage, estrone and catechol estrogens derived from estrone, have been regioselectively labeled with deuterium at the 1-position. Estrone-1-d, estrone-1,2,4-d(3), 4-hydroxyestrone-1-d and 2-hydroxyestrone-1-d have been synthesized with or without deuteriums at the 16-position. The key labeling step involves deuterated trifluoroacetic acid exchange catalyzed by t-butyl alcohol. This economical, straightforward labeling technique makes available a range of estrone compounds containing deuterium at the 1-position. (C) 2014 Elsevier Inc. All rights reserved.