4-Androstene-3,17-dione 3,17-bis(ethylene dithioacetal) | 10455-49-9

• 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: 4-Androstene-3,17-dione 3,17-bis(ethylene dithioacetal)
• 英文别名: 3,3,17,17-bis-ethanediyldimercaptoandrost-4-ene；3,3,17,17-bis-(ethylenedithio)androst-4-ene；3,3;17,17-bis-ethanediyldimercapto-androst-4-ene；3,3;17,17-Bis-aethandiyldimercapto-androst-4-en
• CAS: 10455-49-9
• 化学式: C₂₃H₃₄S₄
• 分子量: 438.787
• InChiKey: HUIHJTUKEKHNOK-SYAJIYQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Androstene-3,17-dione 3,17-bis(ethylene dithioacetal) 以90%的产率得到
  参考文献：
  名称：

  CABALLERO, GERARDO M.;GROS, EDUARDO G., J. CHEM. RES. (S),(1989) N0, C. 320-321

  摘要：

  DOI：
• 作为产物：
  描述：

  睾酮 在 Jones reagent 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.0h， 生成 4-Androstene-3,17-dione 3-ethylene dithioacetal 、 4-Androstene-3,17-dione 3,17-bis(ethylene dithioacetal)
  参考文献：
  名称：

  New Structure–Activity Relationships of A- and D-Ring Modified Steroidal Aromatase Inhibitors: Design, Synthesis, and Biochemical Evaluation

  摘要：

  A- and D-ring androstenedione derivatives were synthesized and tested for their abilities to inhibit aromatase. In one series, C-3 hydroxyl derivatives were studied leading to a very active compound, when the C-3 hydroxyl group assumes 3 beta stereochemistry (1, IC50 = 0.18 mu M). In a second series, the influence of double bonds or epoxide functions in different positions along the A-ring was studied. Among epoxides, the 3,4-epoxide 15 showed the best activity (IC50 = 0.145 mu M) revealing the possibility of the 3,4-oxiran oxygen resembling the C-3 carbonyl group of androstenedione. Among olefins, the 4,5-olefin 12 (IC50 = 0.135 mu M) revealed the best activity, pointing out the importance of planarity in the A,B-ring junction near C-5. C-4 acetoxy and acetylsalicyloxy derivatives were also studied showing that bulky substituents in C-4 diminish the activity. In addition, IFD simulations helped to explain the recognition of the C-3 hydroxyl derivatives (1 and 2) as well as 15 within the enzyme.

  DOI：

  10.1021/jm300262w

文献信息

• Chemoselective (Trans)thioacetalization of Carbonyl Compounds with a Reusable Lewis Acid-Surfactant-Combined Copper Bis(dodecyl sulfate) Catalyst in Water
  作者：Shiue-Shien Weng、Shen-Chun Chang、Tsuan-Hao Chang、Jong-Pyng Chyn、Shu-Wei Lee、Chao-An Lin、Fong-kuang Chen

  DOI：10.1055/s-0029-1218693

  日期：2010.5

  A Lewis acid-surfactant-combined copper bis(dodecyl sulfate) [Cu(DS)2] catalyst served as an efficient and reusable catalyst for the thioacetalization and transthioacetalization of carbonyl compounds and O,O-acetals in water at room temperature. Some of the major advantages of this procedure are high chemoselectivity, ease of operation and purification without any organic solvent, and high yields.

  路易斯酸表面活性剂复合物铜双(十二烷基硫酸) [Cu(DS)2] 催化剂是一种高效且可重复使用的催化剂，在室温下水中催化羰基化合物和O,O-缩醛的硫缩醛化和硫缩醛转移反应。该方法的主要优点包括高化学选择性、操作和纯化简便且无需任何有机溶剂、高产率。
• 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
• Meyer, Acta Endocrinologica, 1957, vol. 25, p. 377,386
  作者：Meyer

  DOI：——

  日期：——