| 138306-84-0

• 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
• CAS: 138306-84-0
• 化学式: C₂₃H₂₈OS₂
• 分子量: 384.607
• InChiKey: MUXYZZFHHCWBJD-FUOQNJDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  在 盐酸 、 氢氧化钾 、 N-氯代丁二酰亚胺 、 trimethylsulfonium iodide 、 sodium hydride 、 silver nitrate 、 lithium diisopropyl amide 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 11β-allenyl-3-oxo-19-nor-17α-pregna-4,9-diene-21,17-carbolactone
  参考文献：
  名称：

  Synthesis of new 11.beta.-substituted spirolactone derivatives. Relationship with affinity for mineralocorticoid and glucocorticoid receptors

  摘要：

  Various steroidal 17-spirolactones substituted in the 11beta-position were synthesized to study the relationship between the nature of the 11beta-arm and their affinity for cytosolic mineralocorticoid (MR) and glucocorticoid (GR) receptors prepared from adrenalectomized rabbit kidney or liver. One of them, the 11beta-allenyl-3-oxo-19-nor-17-pregna-4,9-diene-21,17-carbolactone derivative, exhibited the same affinity for MR as aldosterone and a 5-fold higher affinity than mespirenone. Its affinity for GR was found to be relatively low. As suggested by molecular modeling, the marked differences in mineralocorticoid receptor binding affinity could be related to the structural features induced by this 11beta-allenic substituent.

  DOI：

  10.1021/jm00068a018
• 作为产物：
  描述：

  3,3,17,17-二(乙烯二氧基)-5,10-氧代雌甾-9(11)-烯 在 对甲苯磺酸 、 溶剂黄146 、 copper(l) chloride 作用下， 以 丙酮 为溶剂， 反应 26.5h， 生成
  参考文献：
  名称：

  合成新的10β-炔丙基和11β-烯丙基甾体螺内酯。

  摘要：

  作为关于合成新的，生物学上有趣的11β-取代的甾体螺内酯的持续研究的一部分，我们在这里描述10β-炔丙基化和11β-烯丙基化之间的竞争。将烯丙基溴化镁的格利雅（Grignard）加成至合适的5,10-环氧-9（11）-烯烃可提供10β-炔丙基化或11β-烯丙基化。评价了氯化铜和溶剂的催化作用的作用。据报道，证实了这些新的3,3-亚乙基硫基-10β-炔丙基（或11β-烯基）-19-nor-17α-孕烯-4,9-二烯-21,17-碳内酯的结构分配。

  DOI：

  10.1016/0039-128x(91)90013-l

文献信息

• Synthesis of new 10β-propargylic and 11β-allenic steroidal spirolactones
  作者：Hassane Faraj、Andre Aumelas、Michel Claire、Anne Rondot、Gilles Auzou

  DOI：10.1016/0039-128x(91)90013-l

  日期：1991.11

  As part of continuing studies on the synthesis of new, biologically interesting 11 beta-substituted steroidal spirolactones, we describe here the competition between 10 beta-propargylation and 11 beta-allenylation. Grignard addition of allenyl magnesium bromide to an appropriate 5,10-epoxy-9(11)-olefin provides 10 beta-propargylation or 11 beta-allenylation. The role of the catalytic effect of copper

  作为关于合成新的，生物学上有趣的11β-取代的甾体螺内酯的持续研究的一部分，我们在这里描述10β-炔丙基化和11β-烯丙基化之间的竞争。将烯丙基溴化镁的格利雅（Grignard）加成至合适的5,10-环氧-9（11）-烯烃可提供10β-炔丙基化或11β-烯丙基化。评价了氯化铜和溶剂的催化作用的作用。据报道，证实了这些新的3,3-亚乙基硫基-10β-炔丙基（或11β-烯基）-19-nor-17α-孕烯-4,9-二烯-21,17-碳内酯的结构分配。
• Synthesis of new 11.beta.-substituted spirolactone derivatives. Relationship with affinity for mineralocorticoid and glucocorticoid receptors
  作者：Michel Claire、Hassane Faraj、Gerard Grassy、Andre Aumelas、Anne Rondot、Gilles Auzou

  DOI：10.1021/jm00068a018

  日期：1993.8

  Various steroidal 17-spirolactones substituted in the 11beta-position were synthesized to study the relationship between the nature of the 11beta-arm and their affinity for cytosolic mineralocorticoid (MR) and glucocorticoid (GR) receptors prepared from adrenalectomized rabbit kidney or liver. One of them, the 11beta-allenyl-3-oxo-19-nor-17-pregna-4,9-diene-21,17-carbolactone derivative, exhibited the same affinity for MR as aldosterone and a 5-fold higher affinity than mespirenone. Its affinity for GR was found to be relatively low. As suggested by molecular modeling, the marked differences in mineralocorticoid receptor binding affinity could be related to the structural features induced by this 11beta-allenic substituent.