toluene-4-sulfonic acid 1-ethyl-propyl ester | 950-25-4

• 物质功能分类: 有机原料 - 有机硫化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: toluene-4-sulfonic acid 1-ethyl-propyl ester
• 英文别名: 3-Pentyltosylat；3-pentyl tosylate；Pentyl-3-tosylat；1-Ethylpropyl 4-methylbenzenesulfonate；pentan-3-yl 4-methylbenzenesulfonate
• CAS: 950-25-4
• 化学式: C₁₂H₁₈O₃S
• 分子量: 242.339
• InChiKey: SLMCDJBSBDYBAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid 1-ethyl-propyl ester 在 氢氧化钾 、 硫酸 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (8β)-1-(1-ethylpropyl)-6-methylergoline-8-carboxylic acid, methyl ester
  参考文献：
  名称：

  6-Methylergoline-8-carboxylic acid esters as serotonin antagonists: N1-substituent effects on 5HT2 receptor affinity

  摘要：

  Three series of 6-methylergoline-8-carboxylic acid esters with various alkyl substituents in the N1-position were prepared and their 5HT2 receptor affinities measured. Some overlap occurred in the 5HT2 receptor affinities of the different ester series, indicating that both the ester side chain and the indole substituent influenced 5HT2 receptor affinity. While 5HT2 receptor affinity was affected by the structure of the ester side chain, the N1-substituent played a more crucial role in determining 5HT2 receptor affinity. When the ester side chain was held constant, maximal 5HT2 receptor affinity for that series of esters was obtained when the N1-substituent was isopropyl. Smaller substituents in the N1-position resulted in reduced 5HT2 receptor affinity. Groups C4 or larger in the N1-position resulted in a further decline in 5HT2 receptor affinity. The importance of the N1-substituent in determining 5HT2 receptor affinity was further substantiated when several 2-methyl-3-ethyl-5-(dimethylamino)indoles with various N1-substituents were tested. Again, maximal 5HT2 receptor affinity was obtained when the N1-substituent was isopropyl.

  DOI：

  10.1021/jm00393a024
• 作为产物：
  描述：

  3-戊醇 、 对甲苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到toluene-4-sulfonic acid 1-ethyl-propyl ester
  参考文献：
  名称：

  高亲和力的二氢叶酸还原酶抑制剂：具有较小分子尺寸的7,8-二烷基-1,3-二氨基吡咯并[3,2-f]喹唑啉类药物的抗菌和抗癌活性。

  摘要：

  制备了一系列的7,8-二烷基吡咯并[3,2-f]喹唑啉类化合物作为二氢叶酸还原酶（DHFR）的抑制剂。基于化合物尺寸和抗真菌活性之间明显的反比关系，将化合物设计为相对较小和紧凑。GRID分析法对白色念珠菌DHFR的三维结构进行了辅助设计，表明吡咯并喹唑啉环系统7位和8位相对较小的支链烷基可以提供最佳的相互作用，从而抑制抑制剂的产生。蛋白质。该化合物是有效的真菌和人DHFR抑制剂，K（i）值分别低至7.1和0.1 pM，并且对白色念珠菌和一系列肿瘤细胞系具有高活性。与已知的DHFR亲脂性抑制剂（如曲美曲塞和匹瑞特欣）相反，该系列吡咯并喹唑啉的成员对P-糖蛋白介导的多药耐药性不敏感，并且还显示出在肺和脑组织中的显着分布。该化合物在肺和脑肿瘤模型中具有活性，并显示出对卡氏肺孢子虫和白色念珠菌的体内活性。

  DOI：

  10.1021/jm9505122

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：BORAGEN INC

  公开号：WO2021003501A1

  公开（公告）日：2021-01-07

  The present disclosure describes novel compounds, or their pharmaceutically acceptable salts, pharmaceutical compositions containing them, and their medical uses. Compounds of the disclosure have activity as dual modulators of Janus kinase (JAK), alone, or in combination with one or more of an additional mechanism, including a tyrosine kinase, such as TrkA or Syk, and PDE4, and are useful in the in the treatment or control of inflammation, auto-immune diseases, cancer, and other disorders and indications where modulation of JAK would be desirable. Also described herein are methods of treating inflammation, auto-immune diseases, cancer, and other conditions susceptible to inhibition of JAK and PDE4 by administering a compound herein described.

  本公开描述了新颖的化合物，或其药用可接受的盐，含有它们的药物组合物，以及它们的医疗用途。本公开的化合物具有作为Janus激酶（JAK）的双重调节剂的作用，单独使用，或与一个或多个附加机制（包括酪氨酸激酶，如TrkA或Syk，以及PDE4）结合使用，并且在治疗或控制炎症、自身免疫疾病、癌症以及其他调节JAK会可取的失调和其他适应症中是有用的。此外，还描述了通过施用本处所述的化合物来治疗炎症、自身免疫疾病、癌症以及其他易受JAK和PDE4抑制的状况的方法。
• <i>N</i> ¹-Alkylation of Dihydrolysergic Acid
  作者：Gifford Marzoni、William L. Garbrecht

  DOI：10.1055/s-1987-28037

  日期：——

  A new procedure for alkylating dihydrolysergic acid (1) on the indole nitrogen is reported. Previous procedures involved reaction of the indoyl anion with an alkyl halide. As the alkyl group gets larger, dehydrohalogenation of the alkyl halide becomes the preferred reaction and little or no N 1-alkylation occurs. By using alkyl tosylates in place of alkyl halides, we have been able to alkylate 1 on the indole nitrogen with a wide variety of alkyl groups in high yield.

  报道了一种在吲哚氮上烷基化二氢麦角酸（1）的新方法。先前的方法涉及吲哚阴离子与烷基卤化物的反应。随着烷基集团体积的增大，烷基卤化物的脱卤化氢反应成为主要反应，几乎没有或完全没有N-1位烷基化发生。通过使用对甲苯磺酸酯代替烷基卤化物，我们能够以高产率在吲哚氮上对1进行多种烷基集团的烷基化。
• Substituent effects on cyclobutyl and cyclopropylcarbinyl cations
  作者：Kenneth B. Wiberg、David Shobe、Gordon L. Nelson

  DOI：10.1021/ja00076a024

  日期：1993.11

  the alkyl- and aryl-substituted compounds, the rate-determining step leads to the formation of a bridged cyclobutyl cation which then rearranges to a cyclopropylcarbinyl/homoallyl ion. The value of ρ for the solvolysis of the 3-aryl derivatives was -1.5, suggesting some charge transfer to the 3-position. The 3-chlorocyclobutyl tosylates react to give only the inverted 3-chlorocyclobutyl acetates. The

  检查了 3-取代的甲苯磺酸环丁基酯（X=Ar、Cl 和 OEt）的乙酰水解，给出了速率和产物分布。对于烷基和芳基取代的化合物，限速步骤导致形成桥连的环丁基阳离子，然后重排为环丙基羰基/高烯丙基离子。3-芳基衍生物溶剂分解的 ρ 值为 -1.5，表明一些电荷转移到 3-位。3-氯环丁基甲苯磺酸酯反应仅产生转化的3-氯环丁基乙酸酯。3-乙氧基衍生物产生～1:1的相应乙酸酯混合物。有关这些反应的更多信息是通过 MP2/6-31 * 理论水平的 ab initio MO 计算获得的
• Trisodium heptaphosphide in reactions with alkyl and aryl tosylates
  作者：V. A. Milyukov、A. V. Kataev、E. Hey-Hawkins、O. G. Sinyashin

  DOI：10.1007/s11172-007-0048-6

  日期：2007.2

  Reactions of trisodium heptaphosphide with alkyl tosylates gave dialkylheptaphosphides or trialkylheptaphosphines, depending on the stoichiometric ratios of the starting reagents. A method for determination of the coupling constants of the asymmetric isomer of trialkyl-heptaphosphines was proposed. Reactions of the heptaphosphide trianion with aryl tosylates yielded disodium hexadecaphosphide.

  七磷化三钠与甲苯磺酸烷基酯的反应产生二烷基七磷化物或三烷基七膦，这取决于起始试剂的化学计量比。提出了一种测定三烷基七膦不对称异构体偶联常数的方法。七磷化物三阴离子与甲苯磺酸芳基酯的反应产生十六磷化二钠。
• N-alkylation of dihydrolysergic acid
  申请人：Eli Lilly and Company

  公开号：US04734501A1

  公开（公告）日：1988-03-29

  The present invention provides a process for N-alkylating dihydrolysergic acid with a substituted benzenesulfonate derivative.

  本发明提供了一种使用取代苯磺酸衍生物对二氢莱姆酸进行N-烷基化的方法。