ent-testosterone | 86335-11-7

• 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: ent-testosterone
• 英文别名: (8S,9R,10S,13R,14R,17R)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 86335-11-7
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: MUMGGOZAMZWBJJ-MGYGNFHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  ent-testosterone 在 4-二甲氨基吡啶 、 二环己烷并-18-冠醚-6 、 2,2'-联吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 4 A molecular sieve 、 potassium tert-butylate 、 四丁基氟化铵 、 氢化钾 、 2,6-二叔丁基-4-甲基苯酚钾盐 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 叔丁醇 为溶剂， 反应 54.5h， 生成 ent-cholesterol
  参考文献：
  名称：

  Synthesis of ent-cholesterol, the unnatural enantiomer

  摘要：

  Cholesterol is ubiquitious in mammals and plays an important role in human health. The unique relationship between enantiomers makes ent-cholesterol, the unnatural enantiomer of cholesterol, a valuable new probe of cholesterol function in biochemical systems. We report the first enantioselective total synthesis of ent-cholesterol.

  DOI：

  10.1021/jo00035a036
• 作为产物：
  描述：

  rac-3,3-ethanediyldioxy-androst-5-en-17-one 在 盐酸 、 sodium tetrahydroborate 作用下， 生成 ent-testosterone
  参考文献：
  名称：

  Steroid Total Synthesis—Hydrochrysene Approach. X.¹ Total Synthesis of Testosterone

  摘要：

  DOI：

  10.1021/ja01605a023

文献信息

• Structural and Configurational Dependence of the Sensory Process in Steroids
  作者：G�nther Ohloff、Bruno Maurer、Beat Winter、Wolfgang Giersch

  DOI：10.1002/hlca.19830660121

  日期：1983.2.2

  19-nortestosterone have led to the synthesis of over 60 androstane and estrane derivatives whose sensory evaluation has allowed molecular parameters to be established for release of a ‘steroid-type’ scent. Odor perception with O-containing compounds in both classes has been found to be regioselective1. Osmophoric groups at C(3) were found to be the most active and specific. Functionality at C(2) is accompanied

  睾丸激素和19-去甲睾丸激素的结构修饰已导致合成了60多种雄甾烷和雌二醇衍生物，其感官评估已为释放“类固醇型”气味建立了分子参数。两种类别的含O化合物的气味感知都具有区域选择性1。C（3）处的渗透基团是最活跃和最特异的。C（2）处的功能在很大程度上伴随着原子缺陷，并且在特殊情况下，C（1）和C（4）处的含O取代基似乎会影响受体膜。
• Organoelement derivatives of steroids: synthesis and structural characterization of diorganotin chloride adducts of hormones
  作者：A. Saxena、F. Huber、L. Pellerito、A. Girasolo、G.C. Stocco

  DOI：10.1016/s0020-1693(00)81211-6

  日期：1986.12

  Abstract Ten new diorganotin dichloride adducts of hormones of the type R 2 SnCl 2 ·2L [where R = Me, Et, n-Bu, Oct and Ph; L = 4-androsten-17s-ol-3-one ( A ); 5-androsten-3s-ol-17-one ( B ); 4-androsten-17α- methyl-17s-ol-3-one ( C ) and 3,17-dihydroxy-5- pregnene-20-one ( D )] have been prepared and characterized at 297 K and 223 K. Spectroscopic measurements (IR; Raman; 1 H, 13 C, 119 Sn NMR) suggest

  摘要R 10 SnCl 2·2L型激素的10种新的二氯化二有机锡二氯化物加合物[其中R = Me，Et，n-Bu，Oct和Ph；L = 4-雄酮-17s-ol-3-one（A）; 5-androsten-3s-ol-17-one（B）; 已经制备了4-雄烯酮17α-甲基-17s-ol-3-one（C）和3,17-二羟基-5-孕烯-20-one（D）]，并在297 K和223 K下进行了表征。 （IR; Raman; 1 H，13 C，119 Sn NMR）表明在297 K时溶液会解离或快速交换配体。八面体几何结构中通过羰基氧和反式-R基团键合的六配位加合物在223 K时配制。
• C‐H Functionalization of Heterocycles with Triplet Carbenes by means of an Unexpected 1,2‐Alkyl Radical Migration
  作者：Claire Empel、Sripati Jana、Łukasz Ciszewski、Katarzyna Zawada、Chao Pei、Dorota Gryko、Rene M. Koenigs

  DOI：10.1002/chem.202300214

  日期：——

  A triplet carbene is involved in the C3-H functionalization of indole heterocycles. We herein describe a combined experimental and computational study on this reaction and unveil an unexpected 1,2-alkyl radical migration pathway.

  三线态卡宾参与吲哚杂环的 C3-H 官能化。我们在此描述了对该反应的综合实验和计算研究，并揭示了一种意想不到的 1,2-烷基自由基迁移途径。
• Hu, Yuefei; Wittmer, Lisa L.; Kalkbrenner, Melissa, Journal of the Chemical Society. Perkin transactions I, 1997, # 24, p. 3665 - 3671
  作者：Hu, Yuefei、Wittmer, Lisa L.、Kalkbrenner, Melissa、Evers, Alex S.、Zorumski, Charles F.、Covey, Douglas F.

  DOI：——

  日期：——
• Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens
  作者：Bryson W. Katona、Kathiresan Krishnan、Zu Yun Cai、Brad D. Manion、Ann Benz、Amanda Taylor、Alex S. Evers、Charles F. Zorumski、Steven Mennerick、Douglas F. Covey

  DOI：10.1016/j.ejmech.2007.02.017

  日期：2008.1

  Allopregnanolone (1) and pregnanolone (2), steroids containing a 17 beta-acetyl group, are potent enhancers of GABA (gamma-aminobutyric acid) action at GABA(A) receptors. Their effects are enantioselective with the non-naturally occurring enantiomers (ent-1 and ent-2) being less potent. Androsterone (3) and etiocholanolone (4), steroids with a C-17 carbonyl group, are weak enhancers of GABA action at GABA(A) receptors. Unexpectedly, their enantiomers (ent-3 and ent-4) have been found to have enhanced, not diminished, activity at GABA(A) receptors. Furthermore, the C-17 spiro-epoxide analogues (ent-5 and ent-6) of ent-3 and ent-4, respectively, have activities comparable to those of steroids 1 and 2. The results indicate that some ent-steroids are potent modulators of GABA(A) receptors and might have clinical potential as GABAergic drugs of the future. (C) 2007 Elsevier Masson SAS. All rights reserved.