2-(pyridin-2-yl)ethyl 4-methylbenzenesulfonate | 22320-32-7

• 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: 2-(pyridin-2-yl)ethyl 4-methylbenzenesulfonate
• 英文别名: 2-(2-pyridyl)ethyl tosylate；2-(2-pyridinyl)-ethyl 4-methylbenzenesulfonate；Toluene-4-sulfonic acid 2-pyridin-2-yl-ethyl ester；2-pyridin-2-ylethyl 4-methylbenzenesulfonate
• CAS: 22320-32-7
• 化学式: C₁₄H₁₅NO₃S
• 分子量: 277.344
• InChiKey: BGJNKHGRYOEWMT-UHFFFAOYSA-N

物化性质

• 沸点：
  438.6±33.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(pyridin-2-yl)ethyl 4-methylbenzenesulfonate 在 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 41.0h， 生成 2-(2-bromoethyl)-1-methylpyridinium iodide
  参考文献：
  名称：

  E1cb 和 E2 消除反应机制之间边界区域的证据：吡啶环激活系统的联合实验和理论研究

  摘要：

  我们报告了一项联合实验和理论研究，以表征由吡啶环激活的系统中碱诱导的 β-消除反应的机制，具有卤素离去基团。研究的系统代表了临界情况，其中不确定反应是通过碳负离子中间体（E1cb，A（xh）D（H）+ D（N））还是通过质子和卤化物的协同损失（E2， A(N)D(E)D(N)) 基础攻击。实验上，在 OD(-)/D(2)O 与非消除底物（1-甲基-2-（2-X 乙基）碘化吡啶）中，H/D 交换的 Taft 相关性用于预测与 N-甲基化底物和 F、Cl、Br 作为离去基团的消除反应的速率常数。比较表明 E1cb 不可逆机制与 F，但是用 Cl 和 Br 观察到的偏差不允许得出结论性的分配。理论计算表明，对于具有氟化物离去基团的 N-甲基化底物，通过形成中等稳定的碳负离子进行消除。当离去基团是 Cl 或 Br 以及任何非甲基化物质时，没有发现稳定的阴离子中间体，表明协同消除。然而，尽管机制发生了变化，但与氟化底物相比，含

  DOI：

  10.1021/ja0539138
• 作为产物：
  描述：

  2-羟乙基吡啶 、 对甲苯磺酰氯 在 吡啶 作用下， 以78%的产率得到2-(pyridin-2-yl)ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis, structures of (aminopyridine)nickel complexes and their use for catalytic ethylene polymerization

  摘要：

  一系列α-氨基吡啶类化合物(2,6-C6H3N)(R1)(CHR2NR3R4)(R1 = R2 = H, R3 = H, R4 = iPr (L1a), R4 = tBu (L1b), R4 = Ph (L1c), R4 = 2,6-Me2C6H3 (L1d), R4 = 2,6-iPr2C6H3 (L1e), R1 = R2 = H, R3 = R4 = Et (L1f), R1 = H, R2 = Me, R3 = H, R4 = iPr (L2a), R4 = Ph (L2c), R4 = 2,6-Me2C6H3 (L2d), R4 = 2,6-iPr2C6H3 (L2e), R1 = Me, R2 = H, R3 = H, R4 = 2,6-iPr2C6H3 (L3e))和β-氨基吡啶类化合物(2-C6H4N)(CH2CH2NR1R2)(R1 = H, R2 = iPr (4a), R2 = tBu (L4b), R1 = R2 = Et (L4f))已被合成。通过配体取代反应从(DME)NiBr2合成相应的卤化镍配合物1a–4f,并由X射线晶体学表征其分子结构。通过X射线结晶学确定了四种配位模式,包括单核四配位物种与一个配体、单核五配位物种与两个配体、双核五配位物种与两个配体以及六配位的聚合框架。使用甲基铝氧烷(MAO)作为活化剂,镍配合物可以在中等压力和室温下催化乙烯聚合。活性达到105 g PE mol−1 Ni h。具有高度支化和高度结晶性的PE产品,Mn ∼ 103,PDI < 2。

  DOI：

  10.1039/c2dt30151b

文献信息

• Synthesis, structures of (aminopyridine)nickel complexes and their use for catalytic ethylene polymerization
  作者：Ya-Chi Lin、Kuo-Hsuan Yu、Ya-Fan Lin、Gene-Hsiang Lee、Yu Wang、Shiuh-Tzung Liu、Jwu-Ting Chen

  DOI：10.1039/c2dt30151b

  日期：——

  A series of α-aminopyridines in the form of (2,6-C6H3N)(R1)(CHR2NR3R4) (R1 = R2 = H R3 = H R4 = iPr (L1a), R4 = tBu (L1b), R4 = Ph (L1c), R4 = 2,6-Me2C6H3 (L1d), R4 = 2,6-iPr2C6H3 (L1e), R1 = R2 = H R3 = R4 = Et (L1f), R1 = H R2 = Me R3 = H R4 = iPr (L2a), R4 = Ph (L2c), R4 = 2,6-Me2C6H3 (L2d), R4 = 2,6-iPr2C6H3 (L2e), R1 = Me R2 = H R3 = H R4 = 2,6-iPr2C6H3 (L3e)) and β-aminopyridines in the form of (2-C6H4N)(CH2CH2NR1R2) (R1 = H R2 = iPr (4a), R2 = tBu (L4b), R1 = R2 = Et (L4f)) have been prepared. Their corresponding halonickel complexes 1a–4f are synthesized by ligand substitution from (DME)NiBr2 and the molecular structures are characterized. Four types of coordination modes include four-coordinate mononuclear species with one ligand, five-coordinate mononuclear species with two ligands, five-coordinate dinuclear species with two ligands, and a six-coordinate polymeric framework were determined by X-ray crystallography. Using methylaluminoxanes (MAO) as the activator, the nickel complexes can catalyze ethylene polymerization under moderate pressure and ambient temperature. The activity reaches 105 g PE mol−1 Ni h. The PE products with high branching and high crystallinity have Mn ∼ 103 with PDI < 2.

  一系列α-氨基吡啶类化合物(2,6-C6H3N)(R1)(CHR2NR3R4)(R1 = R2 = H, R3 = H, R4 = iPr (L1a), R4 = tBu (L1b), R4 = Ph (L1c), R4 = 2,6-Me2C6H3 (L1d), R4 = 2,6-iPr2C6H3 (L1e), R1 = R2 = H, R3 = R4 = Et (L1f), R1 = H, R2 = Me, R3 = H, R4 = iPr (L2a), R4 = Ph (L2c), R4 = 2,6-Me2C6H3 (L2d), R4 = 2,6-iPr2C6H3 (L2e), R1 = Me, R2 = H, R3 = H, R4 = 2,6-iPr2C6H3 (L3e))和β-氨基吡啶类化合物(2-C6H4N)(CH2CH2NR1R2)(R1 = H, R2 = iPr (4a), R2 = tBu (L4b), R1 = R2 = Et (L4f))已被合成。通过配体取代反应从(DME)NiBr2合成相应的卤化镍配合物1a–4f,并由X射线晶体学表征其分子结构。通过X射线结晶学确定了四种配位模式,包括单核四配位物种与一个配体、单核五配位物种与两个配体、双核五配位物种与两个配体以及六配位的聚合框架。使用甲基铝氧烷(MAO)作为活化剂,镍配合物可以在中等压力和室温下催化乙烯聚合。活性达到105 g PE mol−1 Ni h。具有高度支化和高度结晶性的PE产品,Mn ∼ 103,PDI < 2。
• Copper-Chelating Azides for Efficient Click Conjugation Reactions in Complex Media
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  DOI：10.1002/anie.201310671

  日期：2014.6.2

  chelation‐assisted copper catalysis was employed for the development of new azides that display unprecedented reactivity in the copper(I)‐catalyzed azide–alkyne [3+2] cycloaddition (CuAAC) reaction. Azides that bear strong copper‐chelating moieties were synthesized; these functional groups allow the formation of azide copper complexes that react almost instantaneously with alkynes under diluted conditions. Efficient

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• Opioid ligands with mixed properties from substituted enantiomeric <i>N</i>-phenethyl-5-phenylmorphans. Synthesis of a µ-agonist δ-antagonist and δ-inverse agonists
  作者：Kejun Cheng、In Jong Kim、Mei-Jing Lee、Steven A. Adah、Tyler J. Raymond、Edward J. Bilsky、Mario D. Aceto、Everette L. May、Louis S. Harris、Andrew Coop、Christina M. Dersch、Richard B. Rothman、Arthur E. Jacobson、Kenner C. Rice

  DOI：10.1039/b618875c

  日期：——

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  作者：Peng Ren、Lucas-Alexandre Stern、Xile Hu

  DOI：10.1002/anie.201204275

  日期：2012.9.3

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  作者：Gregory W. O’Neil、Nathan D. Drake、Jennifer M. Storvick

  DOI：10.1016/j.tetlet.2012.12.049

  日期：2013.2

  2-(Phenylsulfonyl)ethyl pyridines can be coupled with aldehydes leading directly to sulfone-eliminated vinylpyridine allylic alcohols. These products are obtained in good yield and with high levels of stereocontrol.

  2-（苯磺酰基）乙基吡啶可以与醛偶联，直接导致砜消除的乙烯基吡啶烯丙基醇。这些产品以高收率和高水平的立体控制获得。