3-(p-Toluolsulfonamido)-propyl-p-toluolsulfonat | 51425-88-8

• 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: 3-(p-Toluolsulfonamido)-propyl-p-toluolsulfonat
• 英文别名: 3-[(4-Methylbenzene-1-sulfonyl)amino]propyl 4-methylbenzene-1-sulfonate；3-[(4-methylphenyl)sulfonylamino]propyl 4-methylbenzenesulfonate
• CAS: 51425-88-8
• 化学式: C₁₇H₂₁NO₅S₂
• 分子量: 383.489
• InChiKey: UVQOVWOIXDPYEB-UHFFFAOYSA-N

物化性质

• 沸点：
  563.0±60.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(p-Toluolsulfonamido)-propyl-p-toluolsulfonat 在 sodium azide 作用下， 反应 6.0h， 生成 3-azido-N-tosylpropan-1-amine
  参考文献：
  名称：

  Fragment-based discovery of novel and selective mPGES-1 inhibitors Part 1: Identification of sulfonamido-1,2,3-triazole-4,5-dicarboxylic acid

  摘要：

  Microsomal prostaglandin E synthase-1 (mPGES-1) is an inducible prostaglandin E synthase that catalyzes the conversion of prostaglandin PGH(2) to PGE(2) and represents a novel target for therapeutic treatment of inflammatory disorders. It is essential to identify mPGES-1 inhibitor with novel scaffold as new hit or lead compound for the purpose of the next-generation anti-inflammatory drugs. Herein we report the discovery of sulfonamido-1,2,3-triazole-4,5-dicarboxylic derivatives as a novel class of mPGES-1 inhibitors identified through fragment-based virtual screening and in vitro assays on the inhibitory activity of the actual compounds. 1-[2-(N-Phenylbenzenesulfonamido)ethyl]-1H-1,2,3-triazole-4,5-dicarboxylic acid (6f) inhibits human mPGES-1 (IC50 of 1.1 mu M) with high selectivity (ca. 1000-fold) over both COX-1 and COX-2 in a cell-free assay. In addition, the activity of compound 6f was again tested at 10 mu M concentration in presence of 0.1% Triton X-100 and found to be reduced to 1/4 of its original activity without this detergent. Compared to the complete loss of activity of nuisance inhibitor with the detergent, therefore, compound 6f would be regarded as a partial nuisance inhibitor of mPGES-1 with a novel scaffold for the optimal design of more potent mPGES-1 inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.019
• 作为产物：
  描述：

  1,3-丙二醇-二-间-甲苯磺酸盐 、 对甲苯磺酰胺 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以24%的产率得到3-(p-Toluolsulfonamido)-propyl-p-toluolsulfonat
  参考文献：
  名称：

  用双金属 Rh(II) 催化剂通过丙二烯加氢胺化形成中型和大型 N-杂环

  摘要：

  我们报告了一种 2-膦基咪唑衍生的双金属 Rh(II) 配合物的合成，该配合物使分子内丙二烯氢化胺化以高产率形成 7 至 10 元环。相反，单金属 Rh 配合物不能形成任何产物。我们展示了形成各种N-杂环的广泛底物范围。还展示了形成 11 至 15 元N杂环的大环化。机理研究表明，该反应通过可逆的丙二烯与 Rh 氢化物的插入进行，然后是 C-N 键形成还原消除。我们假设用我们的催化剂与单金属 Rh 配合物观察到的反应性源自我们配合物的双金属性质。

  DOI：

  10.1021/jacs.1c10534

文献信息

• Cu(II) Porphyrin-catalyzed Coupling of Alkyl Tosylates and Grignard Reagents
  作者：Iori Matsuoka、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1246/cl.200064

  日期：2020.5.5

  Copper(II) porphyrin-catalyzed coupling of alkyl tosylates and alkyl Grignard reagents afforded substituted alkanes. The role of the copper(II) porphyrin complex was examined using EPR and in-situ ...

  铜 (II) 卟啉催化的甲苯磺酸烷基酯和烷基格氏试剂的偶联得到取代的烷烃。使用 EPR 和原位...
• Reductive Hydroxymethylation of 4‐Heteroarylpyridines
  作者：Hamish B. Hepburn、Timothy J. Donohoe

  DOI：10.1002/chem.202000060

  日期：2020.2.11

  reaction to proceed smoothly, facilitating the preparation of useful 3D heteroaryl-substituted functionalized piperidines. The methodology is used to prepare 3-hydroxymethylated analogues of pharmaceutical agents. Mechanistically, formaldehyde acts as both a hydride donor and the electrophile, leading to the formation of two new carbon-hydrogen bonds and one new carbon-carbon bond under relatively mild conditions

  用吸电子杂环活化吡啶鎓盐可使铱催化的还原性羟甲基化反应顺利进行，从而有助于制备有用的3D杂芳基取代的官能化哌啶。该方法用于制备药物的3-羟甲基化类似物。从机理上讲，甲醛既充当氢化物供体又充当亲电试剂，导致在相对温和的条件下形成两个新的碳氢键和一个新的碳碳键。
• Bennet; Somayaji; Brown, Journal of the American Chemical Society, 1991, vol. 113, # 20, p. 7563 - 7571
  作者：Bennet、Somayaji、Brown、Santarsiero

  DOI：——

  日期：——
• Synthesis of chiral N-alkyl-cyclopentadienyl sulfonamides
  作者：Cornelis Lensink

  DOI：10.1016/0957-4166(95)00264-p

  日期：1995.8

  The reaction of sodium cyclopentadiene or lithium indene with tosylamino tosylates of amino alcohols yield a series of novel N-alkylcyclopentadiene sulfonamides. These cyclopentadiene derivatives are potential ligands capable of chelating to transition metals. Optically active derivatives were prepared starting from chiral beta-amino alcohols.
• Medium and Large <i>N</i>-Heterocycle Formation via Allene Hydroamination with a Bimetallic Rh(II) Catalyst
  作者：Kelton G. Forson、Benjamin O. Bohman、Coriantumr Z. Wayment、Rachel N. Owens、Caitlyn E. McKnight、Rhen C. Davis、Lillian R. Stillwell、Stacey J. Smith、David J. Michaelis

  DOI：10.1021/jacs.1c10534

  日期：2022.1.12

  We report the synthesis of a 2-phosphinoimidazole-derived bimetallic Rh(II) complex that enables intramolecular allene hydroamination to form 7- to 10-member rings in high yield. Monometallic Rh complexes, in contrast, fail to achieve any product formation. We demonstrate a broad substrate scope for formation of various N-heterocycles. Macrocyclizations that form 11- to 15-member N-heterocycles are

  我们报告了一种 2-膦基咪唑衍生的双金属 Rh(II) 配合物的合成，该配合物使分子内丙二烯氢化胺化以高产率形成 7 至 10 元环。相反，单金属 Rh 配合物不能形成任何产物。我们展示了形成各种N-杂环的广泛底物范围。还展示了形成 11 至 15 元N杂环的大环化。机理研究表明，该反应通过可逆的丙二烯与 Rh 氢化物的插入进行，然后是 C-N 键形成还原消除。我们假设用我们的催化剂与单金属 Rh 配合物观察到的反应性源自我们配合物的双金属性质。