(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl methanesulfonate | 3381-23-5

• 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: (8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl methanesulfonate
• 英文别名: 3-mesylestrone；3-methanesulphonyloxy-oestra-1,3,5(10)-trien-17-one；[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] methanesulfonate
• CAS: 3381-23-5
• 化学式: C₁₉H₂₄O₄S
• 分子量: 348.463
• InChiKey: LOGOAZBRSNBVIZ-VXNCWWDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl methanesulfonate 以 溶剂黄146 为溶剂， 生成 9α,11β-Dihydroxy3-methanesulphonyl-oxy-oestra-1,3,5(10)-trien-17-one 11β-nitrate
  参考文献：
  名称：

  Process for the preparation of 11-.beta.-nitro-oxysteroids

  摘要：

  制备含有芳香环A的9-α-羟基-11-β-硝基氧化甾体的过程，其中在硝酸根离子存在下，芳香环A-环含有的9,11-未取代类固醇或相应的9,11-去氢类固醇被氧化为偶氮离子。

  公开号：

  US03980681A1
• 作为产物：
  描述：

  estrone benzene sulfonate 在 吡啶 作用下， 以 甲醇 为溶剂， 生成 (8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl methanesulfonate
  参考文献：
  名称：

  某些雌酮芳基和甲基磺酸盐在溶液中的光化学行为：制备和机理研究

  摘要：

  在稳态条件下研究了在氮气氛下不同有机溶剂中雌酮芳基酯和甲基磺酸酯的直接辐照。雌酮衍生物通过涉及 [1;3]-磺酰基迁移的 photo-Fries 重排反应有效地反应，提供邻磺酰基雌酮衍生物和雌酮作为光产物。此外，雌酮和 2-芳基磺酰基雌酮衍生物通过 Norrish I 型反应进行差向异构化。还进行了光反应的化学淬灭和光敏化实验，以建立光反应激发态。同样，还研究了溶剂效应和磺酰基对光反应的性质。

  DOI：

  10.1111/php.13272

文献信息

• Nickel-Catalyzed Cyanation of Phenol Derivatives with Zn(CN)₂ Involving C–O Bond Cleavage
  作者：Yi Gan、Gaonan Wang、Xin Xie、Yuanhong Liu

  DOI：10.1021/acs.joc.8b02498

  日期：2018.11.16

  An efficient nickel-catalyzed cyanation of aryl sulfonates, fluorosulfonates, and sulfamates with Zn(CN)2 was developed, which provides a facile access to the nitrile products in generally good to excellent yields. The reaction is accomplished by using NiII complex as the precatalyst and DMAP as the additive. The method also displays wide functional group compatibility; for example, keto, methoxy,

  开发了一种有效的镍催化的芳基磺酸盐，氟磺酸盐和氨基磺酸盐与Zn（CN）2的氰化氰化物，该方法可轻松获得腈产品，通常收率良好，收率极佳。该反应是通过使用Ni II配合物作为预催化剂和DMAP作为添加剂来完成的。该方法还显示了广泛的功能组兼容性。例如，在反应过程中，酮，甲氧基，N，N-二甲基氨基，氰基，酯和吡啶基具有良好的耐受性。
• Synthesis, Biological Evaluation and the Rationalisation of the Inhibitory Activity of a Range of Sulfonate Derivatives of Estrone (E1) in the Design of Reversible Inhibitors of Estrone Sulfatase (ES)
  作者：Mohsen Akbarzadeh、Timothy Cartledge、Sabbir Ahmed

  DOI：10.2174/1570180811666140226235116

  日期：2014.8.8

  Sulfonate derivatives of estrone (E1) were designed and synthesized as potential reversible inhibitors of E1 sulfatase (ES). The results of the biochemical evaluation show the compounds to be weak inhibitors in comparison to the irreversible inhibitor E1-3-O-sulfamate, however, two compounds were found to possess good inhibitory activity.

  雌酮（E1）的磺酸盐衍生物被设计和合成作为E1磺酸酯酶（ES）的可能可逆抑制剂。生化评估结果显示，与不可逆抑制剂E1-3-O-磺酰胺相比，这些化合物作为较弱的抑制剂，然而，发现其中两种化合物具有良好的抑制活性。
• Nickel-Catalyzed N-Arylation of Primary Amides and Lactams with Activated (Hetero)aryl Electrophiles
  作者：Christopher M. Lavoie、Preston M. MacQueen、Mark Stradiotto

  DOI：10.1002/chem.201605095

  日期：2016.12.23

  The first nickel‐catalyzed N‐arylation of amides with (hetero)aryl (pseudo)halides is reported, enabled by use of the air‐stable pre‐catalyst (PAd‐DalPhos)Ni(o‐tolyl)Cl (C1). A range of structurally diverse primary amides and lactams were cross‐coupled successfully with activated (hetero)aryl chloride, bromide, triflate, tosylate, mesylate, and sulfamate electrophiles.

  据报道，使用空气稳定的预催化剂（PAd-DalPhos）Ni（o -tolyl ）Cl（C1）可以使酰胺与（杂）芳基（假）卤化物进行第一个镍催化的N-芳基化反应。一系列结构多样的伯酰胺和内酰胺已与活化的（杂）芳基氯，溴化物，三氟甲磺酸盐，甲苯磺酸盐，甲磺酸盐和氨基磺酸亲电子试剂成功交叉偶联。
• Product selectivity in the photoreaction of aryl sulfonates and mesylate of estrone derivatives in sustainable and micellar media: a steady-state investigation
  作者：Matías I. Quindt、Gabriel F. Gola、Cristian R. Rodriguez、Javier A. Ramirez、Sergio M. Bonesi

  DOI：10.1039/d2nj02989h

  日期：——

  17-norestrone) was obtained due to the nature of the surfactant, i.e., cationic, anionic, or neutral. Certainly, micelles provide confinement of sulfonic esters within the hydrophobic core, inhibiting the diffusion of the photogenerated radical species into the bulk solution. Because the photoreaction was studied in micellar solutions, the measurement of the binding constant Kb and the estimation of the location

  成功地对一系列芳基磺酸盐和雌酮和 17-炔诺酮衍生物的甲磺酸盐在密闭和可持续胶束环境中的光化学反应进行了制备和机理研究，并在甲醇溶液中进行了光化学行为检查。由于表面活性剂的性质，获得了有利于形成作为主要光产物的邻位区域异构体而不是形成雌酮（或 17-炔诺酮）的显着选择性，即、阳离子、阴离子或中性。当然，胶束将磺酸酯限制在疏水核内，从而抑制光生自由基物质扩散到本体溶液中。因为光反应是在胶束溶液中研究的，所以结合常数K b的测量并且使用紫外-可见光、1D-NMR 和 2D-​​NMR 光谱研究成功地估计了胶束疏水核心内类固醇的位置。结合常数值和微分化学位移 (DCS) 分析显示了磺酸盐在疏水核内的溶解。此外，核 Overhauser 效应光谱 (NOESY) 实验清楚地证明了磺酸盐在胶束内的位置。同样，扩散有序光谱 (DOSY) 实验明确表明，类固醇和胶束表现得像一个独特的超分子实体。
• Estrone sulfonates as inhibitors of estrone sulfatase
  作者：Nicola M. Howarth、Atul Purohit、Michael J. Reed、Barry V.L. Potter

  DOI：10.1016/s0039-128x(96)00243-7

  日期：1997.4

  In our continuing quest to design efficient inhibitors of estrone sulfatase activity and to assess the recognition of estrone sulfate surrogates by estrone sulfatase, we synthesized and evaluated several sulfonate derivatives of 5,6,7,8-tetrahydronaphth-2-ol and estrone. 5,6,7, 8-Tetrahydronaphth-2-methanesulfonate (II), and 5,6,7, 8-tetra-hydronaphth-2-(p-toluene)sulfonate (12) were found not to inhibit estrone sulfatase activity; estrone-3-methane-sulfonate (5), estrone-3-ethanesulfonate (6), estrone-3-butanesulfonate (7), and estrone-3-[(+)10-camphor]sulfonate (8) all weakly inhibited estrone sulfatase, and the best inhibitor from this class of compounds, was estrone-3-(p-toluene)sulfonate (9). At 10 mu M, it inhibited estrone sulfatase activity by 91%. These results emphasize some of the requirements needed for high-affinity binding to the enzyme. (C) 1997 by Elsevier Science Inc.