4-甲基苯磺酸,非3-炔-1-醇 | 85612-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲基苯磺酸,非3-炔-1-醇
• 英文名称: 1-nonan-3-ynyl tosylate
• 英文别名: 3-nonyne-1-ol tosylate；tosylate de nonyne-4-ol-1；toluene-4-sulfonic acid non-3-ynyl ester；non-3-yn-1-yl 4-methylbenzenesulfonate；Non-3-ynyl 4-methylbenzenesulfonate
• CAS: 85612-94-8
• 化学式: C₁₆H₂₂O₃S
• 分子量: 294.415
• InChiKey: TZQLRNRMHAJTCK-UHFFFAOYSA-N

物化性质

• 沸点：
  423.5±28.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  7
• 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：

  4-甲基苯磺酸,非3-炔-1-醇 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以87%的产率得到1-Azido-non-3-yne
  参考文献：
  名称：

  Knouzi, Noureddine; Vaultier, Michel; Carrie, Robert, Bulletin de la Societe Chimique de France, 1985, # 5, p. 815 - 819

  摘要：

  DOI：
• 作为产物：
  描述：

  3-壬炔-1-醇 、 对甲苯磺酰氯 生成 4-甲基苯磺酸,非3-炔-1-醇
  参考文献：
  名称：

  Smooth muscle contractile activities of leukotriene analogues.

  摘要：

  对白三烯亲水和疏水区域的化学修饰进行了研究，以探讨其对平滑肌收缩活性的影响。疏水区域的共轭二烯或三烯部分对强大的收缩活性至关重要。C-6位置的亲水区域的活性不仅依赖于氨基酸或肽；某些含杂环化合物也可以替代使用。

  DOI：

  10.1248/cpb.31.3326

文献信息

• Cross-coupling reactions between some allyl, homoallyl, and homopropargyl substrates and trialkylalanes or dialkyl- and diaryl-magnesium derivatives *
  作者：G.A. Tolstikov、U.M. Dzhemilev

  DOI：10.1016/0022-328x(85)87328-9

  日期：1985.9

  Trialkylalanes and dialkyl- and diaryl-magnesium derivatives can be cross-coupled with allyl ethers and esters, sulphides, and quaternized allylamines. The reactions proceed uncatalyzed either with mild conditions or in the presence of copper complex catalysts to result in high yields of mono- and di-olefins of various structures.

  三烷基丙二烯以及二烷基和二芳基镁衍生物可以与烯丙基醚和酯，硫化物和季铵化烯丙基胺交联。该反应在温和条件下或在铜络合物催化剂的存在下未催化地进行，从而导致高产率的各种结构的单烯烃和二烯烃。
• Design, Synthesis, and Biological Evaluation of <i>N</i>-Alkylated Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus Infection
  作者：Wenquan Yu、Tina Gill、Lijuan Wang、Yanming Du、Hong Ye、Xiaowang Qu、Ju-Tao Guo、Andrea Cuconati、Kang Zhao、Timothy M. Block、Xiaodong Xu、Jinhong Chang

  DOI：10.1021/jm300171v

  日期：2012.7.12

  We recently described the discovery of oxygenated N-alkyl deoxynojirimycin (DNJ) derivative 7 (CM-10-18) with antiviral activity against dengue virus (DENY) infection both in vitro and in vivo. This imino sugar was promising but had an EC50 against DENY in BHK cells of 6.5 mu M, which limited its use in in vivo. Compound 7 presented structural opportunities for activity relationship analysis, which we exploited and report here. These structure activity relationship studies led to analogues 2h, 2l, 3j, 3l, 3v, and 4b-4c with nanomolar antiviral activity (EC50 = 0.3-0.5 mu M) against DENY infection, while maintaining low cytotoxicity (CC50 > 500 mu M, SI > 1000). In male Sprague-Dawley rats, compound 3l was well tolerated at a dose up to 200 mg/kg and displayed desirable PK profiles, with significantly improved bioavailability (F = 92 +/- 4%).
• Cellular uptake of a catechol iron chelator and chloroquine into Plasmodium falciparum infected erythrocytes
  作者：Akli Hammadi、Florence Ramiandrasoa、Veronique Sinou、Christophe Rogier、Thierry Fusai、Jacques Le Bras、Daniel Parzy、Gerhard Kunesch、Bruno Pradines

  DOI：10.1016/s0006-2952(03)00042-x

  日期：2003.4

  Our study demonstrates the capacity of FR160, a catechol iron chelator, to reach and accumulate into infected Plasmodium falciparum erythrocytes and parasites (cellular accumulation ratio between 12 and 43). Steady-state FR160 accumulation is obtained after 2 hr of exposure. After 2 hr exposure, it reaches intracellular levels that are 4- to 10-fold higher in infected red blood cells than those attained in normal erythrocytes. There is quite a good correlation between the accumulation of chloroquine and FR160 in the different strains (r = 0.939) and in the IC50 values (r = 0.719). In contrast, the accumulation of FR160 and its activity is poorly correlated (r = 0.500), suggesting that activity of FR160 may be independent of its penetration into infected erythrocytes. The mechanism of accumulation is yet unknown but based on inhibitor studies, the uptake of FR160 seems to be not associated with the calcium pump or channel, the potassium channel or the Na+/H+ exchanger. Combinations of FR160 with verapamil, diltiazem, clotrimazole, amiloride, diazoxide, 4-aminopyridine, and picrotoxin should be avoided (antagonistic effects). The potent in vitro activity of FR160 on chloroquine-resistant strains or isolates, its lower toxicity against Vero cells, its mechanisms of action, its capacity to reach rapidly and accumulate into infected erythrocytes suggest that FR160 holds much promise as a new structural lead and effective antimalarial agent or at least a promising adjuvant in treatment of malaria. (C) 2003 Elsevier Science Inc. All rights reserved.
• Enantiospecific syntheses of leukotrienes C4, D4, and E4, and [14,15-3H2]leukotriene E4 dimethyl ester
  作者：Noal Cohen、Bruce L. Banner、Rocco J. Lopresti、Frederick Wong、Michael Rosenberger、Yu Ying Liu、Edna Thom、Arnold A. Liebman

  DOI：10.1021/ja00349a053

  日期：1983.6
• Triple bond participation in the alkylation of homopropargyl tosylates by trialkylaluminum
  作者：G. A. Tolstikov、A. Yu. Spivak、L. M. Khalilov

  DOI：10.1007/bf00949021

  日期：1984.6