n-nonyl tosylate | 67334-34-3

• 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: n-nonyl tosylate
• 英文别名: nonyl 4-methylbenzenesulphonate；nonyl 4-methylbenzenesulfonate；1-Nonyl-p-toluolsulfonat；1-nonyl 4-methylbenzenesulfonate；p-toluenesulfonic acid nonyl ester；(n-nonyl)O(p-toluenesulfonyl)；nonyl p-toluenesulfonate；1-nonyl tosylate；Nonyl 4-methylbenzene-1-sulfonate
• CAS: 67334-34-3
• 化学式: C₁₆H₂₆O₃S
• 分子量: 298.447
• InChiKey: BKUGMZHCBXZVJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  n-nonyl tosylate 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 2-(N,N-dimethyl-N-nonylaminio) ethyl octyl phosphate
  参考文献：
  名称：

  Synthesis of structural analogues of hexadecylphosphocholine and their antineoplastic, antimicrobial and amoebicidal activity

  摘要：

  Twelve derivatives of hexadecylphosphocholine (miltefosine) were synthesized to determine how the position and length of the alkyl chain within the molecule influence their biological activities. The prepared alkylphosphocholines have the same molecular formula as miltefosine. Activity of the compounds was studied against a spectrum of tumour cells, two species of protozoans, bacteria and yeast. Antitumour efficacy of some alkylphosphocholines measured up on MCF-7, A2780, HUT-78 and THP-1 cell lines was higher than that of miltefosine. The compounds showed antiprotozoal activity against Acanthamoeba lugdunensis and Acanthamoeba quina. Some of them also possess fungicidal activity against Candida albicans equal to miltefosine. No antibacterial activity was observed against Staphylococcus aureus and Escherichia coil. A difference in position of a long hydrocarbon chain within the structure with maximum efficacy was observed for antitumour, antiprotozoal and antifungal activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.014
• 作为产物：
  描述：

  对甲苯磺酰氯 、 1-壬醇 在 potassium carbonate 、 1-十六烷基咪唑 作用下， 以 水 为溶剂， 反应 4.0h， 以89%的产率得到n-nonyl tosylate
  参考文献：
  名称：

  在无溶剂条件下用于Schotten-Baumann型甲苯磺酸的两亲有机催化剂

  摘要：

  N-十六烷基咪唑催化剂可在含K 2 CO 3的水中有效地进行伯醇与甲苯磺酰氯的甲苯磺酸酯化反应。带有疏水性亚甲基链的催化剂的聚集体用作有机溶剂的替代物。

  DOI：

  10.1021/ol900125y

文献信息

• Chemoselective Three‐Component Geminal Cross Couplings of Dihaloalkanes with Cr Catalysis: Rapid Access to Tertiary and Quaternary Alkanes via a Metal–Carbene Intermediate
  作者：Sha Wang、Linhong Long、Xiaoyu Zhang、Liang Ling、Hui Chen、Xiaoming Zeng

  DOI：10.1002/anie.202312856

  日期：2023.10.26

  The three-component geminal couplings have been achieved by design of a chromium catalytic system using dihaloalkanes to selective react with organomagnesium and chlorosilanes/alkyl tosylates. These newly developed reactions are effective for rapidly forming tertiary and quaternary alkanes via a Cr carbene intermediate with a novel inner-sphere radical coupling mechanism, showing great potential in

  三组分孪生偶联是通过设计铬催化系统来实现的，该系统使用二卤代烷烃选择性地与有机镁和氯硅烷/甲苯磺酸烷基酯反应。这些新开发的反应可有效通过具有新颖内球自由基耦合机制的Cr卡宾中间体快速形成叔烷烃和季烷烃，在合成和药物化学中显示出巨大的潜力。
• Antimicrobial activity of pyrimidinophanes with thiocytosine and uracil moieties
  作者：Vyacheslav E. Semenov、Anatoly S. Mikhailov、Alexandra D. Voloshina、Natalia V. Kulik、Alexandra D. Nikitashina、Vladimir V. Zobov、Sergey V. Kharlamov、Shamil K. Latypov、Vladimir S. Reznik

  DOI：10.1016/j.ejmech.2011.05.034

  日期：2011.9

  Reactions of pyrimidinophanes with two 6-methylthiocytosine and one 5(6)-alkyluracil moieties bridged with each other by polymethylene spacers with methyl or nonyl p-toluenesulfonate, p-toluenesulfonic acid, methanesulfonate and trifluorosulfonate afforded amphiphilic macrocyclic bis-p-toluene-, methane- and trifluorosulfonates. Despite the presence of several reaction centers in the initial pyrimidinophane molecules, protonation and methylation occurred only at the N-1 atom (with quaternization) of the 6-methylthiocytosine moieties. The bacteriostatic and fungistatic activity of the products was estimated. Macrocyclic tosylates exhibit a remarkable selectivity towards Staphylococcus aureus, with MIC values comparable with a reference drug. Bacteriostatic activity of the amphiphilic pyrimiclinophanes depends on the size of the macrocycles, and the highest activity corresponds to definite lengths of polymethylene bridges. Besides, the antimicrobial activity of the screened pyrimidine derivatives depends on their topology. While macrocyclic tosylates are more active against bacteria than against fungi, acyclic tosylate with the same structural fragments shows a dramatical decrease of MIC towards mold and yeast with respect to the corresponding macrocycle. It is found that macrocyclic and acyclic tosylates in high dilutions decrease the extracellular lipase activity. (C) 2011 Elsevier Masson SAS. All rights reserved.
• An efficient, one-pot synthesis of trithiocarbonates from alcoholic tosylates using the Cs2CO3/CS2 system
  作者：Devdutt Chaturvedi、Nisha Mishra、Amit K. Chaturvedi、Virendra Mishra

  DOI：10.1007/s00706-008-0956-7

  日期：2008.12

  A single-step novel protocol for the preparation of symmetrical trithiocarbonates from a corresponding variety of primary, secondary, and tertiary alcoholic tosylates using the Cs2CO3/CS2 system, was developed. This protocol is mild and more efficient than the reported methods.
• Synthesis of long alkyl chain mono-and di-N-substituted 4-amino-N-methylphthalimides. Comparison of N-alkylation methods
  作者：David S. Amarilio、Fannie S. Varveri

  DOI：10.1007/bf00809358

  日期：1991.3

  4-Amino-N-methylphthalimide, 1, was N-alkylated with the respective n-alkyl sulfonates and halides. In the former case, the di-derivative 4 was favored, while in the latter case, under phase transfer catalysis, the mono-derivative 3 was predominant.
• Tellurium in organic synthesis: the enantioselective synthesis of the pheromone blend components of Mayetiola destructor, Drosophila mulleri and Contarinia pisi
  作者：Renan S. Ferrarini、João V. Comasseto、Alcindo A. Dos Santos

  DOI：10.1016/j.tetasy.2009.08.003

  日期：2009.9

  The components of the pheromone blend of Mayetiola destructor, Drosophila mulleri, and Contarinia pisi were synthesized in high enantiomeric excess (99% ee) from a common enantiopure dianion prepared from an enantiopure hydroxytelluride. (C) 2009 Elsevier Ltd. All rights reserved.