3,3-乙二基二巯基孕-4-烯-20-酮 | 63883-02-3

• 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
• 中文名称: 3,3-乙二基二巯基孕-4-烯-20-酮
• 英文名称: 3,3-ethanediyldimercaptopregn-4-en-20-one
• 英文别名: 3,3-Aethandiyldimercapto-pregn-4-en-20-on；1-[(8S,9S,10R,13S,14S,17S)-10,13-dimethylspiro[1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dithiolane]-17-yl]ethanone
• CAS: 63883-02-3
• 化学式: C₂₃H₃₄OS₂
• 分子量: 390.654
• InChiKey: LLUZFOAJCNHFDF-GFJXEVPCSA-N

物化性质

• 沸点：
  518.5±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  3,3-乙二基二巯基孕-4-烯-20-酮 在 silica gel 、 copper(II) sulfate 作用下， 以 苯 为溶剂， 反应 14.0h， 以83%的产率得到黄体酮
  参考文献：
  名称：

  吸附在硅胶上的硫酸铜(II)促进硫缩醛裂解的机理

  摘要：

  吸附在硅胶上的硫酸铜 (II) 裂解硫缩醛的可能机制包括：硫原子和铜 (II) 之间形成螯合物，之前与硅胶表面的羟基配位，随后通过硅胶表面的羟基。

  DOI：

  10.1515/znb-1997-0921
• 作为产物：
  描述：

  黄体酮 、 1,2-乙二硫醇 在 四氯化碲 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以80%的产率得到3,3-乙二基二巯基孕-4-烯-20-酮
  参考文献：
  名称：

  四氯化碲作为温和有效的二硫缩醛催化剂

  摘要：

  通过使用少量的四氯化碲作为温和的路易斯酸催化剂，多种醛和脂肪族酮在室温下以良好的产率转化为相应的二硫缩醛。

  DOI：

  10.1016/s0040-4039(00)78902-7

文献信息

• Catalytic carbon–sulfur bond formation by amphoteric vanadyl triflate: exploring with thia-Michael addition, thioacetalization, and transthioacetalization reactions
  作者：Chien-Tien Chen、Yow-Dzer Lin、Cheng-Yuan Liu

  DOI：10.1016/j.tet.2009.10.012

  日期：2009.12

  A series of thiols have been examined as protic nucleophiles for Michael-type additions to alpha,beta-unsaturated carbonyls as well as double nucleophilic condensations with aldehydes, ketones, and acetals catalyzed by amphoteric, water-tolerant vanadyl triflate under mild and neutral conditions. The newly developed C-S bond formation protocols were carried out smoothly in good to high yields in a highly chemoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.
• Differentiation between carbonyls and acetals in 1,3-dithiane and 1,3-dithiolane synthesis catalyzed by organotin triflates
  作者：Tsuneo Sato、Junzo Otera、Hitosi Nozaki

  DOI：10.1021/jo00070a038

  日期：1993.8

  Carbonyls and acetals are converted to 1,3-dithianes and -dithiolanes upon treatment with 2-stanna-1,3-dithianes and -dithiolanes under catalysis by organotin triflates. In these competition reactions, various types of carbonyls and acetals are differentiated. Aldehydes react preferentially over ketones, but the preference is completely reversed in the competition reactions between the corresponding acetals and ketals. The reactivity of aliphatic aldehydes is greater than that of the acetals of aliphatic aldehydes and ketones. Conversely, an aromatic acetal is more reactive than its parent aldehyde. In the competition between aromatic and aliphatic aldehydes, the reaction of the latter predominates. However, aromatic acetals react preferentially over aliphatic acetals. Ketones of different types are also differentiated. No such discrimination can be achieved by conventional methods. Organotin triflates are capable of detecting subtle differences in the reactivity of carbonyls and acetals. Such unique differentiation can be explained in terms of the dependence of the reaction path on the substrate: the reactions of carbonyls are initiated by coordination to tin, whereas the reactions of acetals proceed via oxocarbenium ion intermediates.
• Selective Mercaptole Formation of Steroid Ketones
  作者：Jack W. Ralls、Byron Riegel

  DOI：10.1021/ja01646a064

  日期：1954.9