1-phenylethyl tosylate | 6749-54-8

• 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: 1-phenylethyl tosylate
• 英文别名: 1-phenylethyl p-toluenesulfonate；p-Toluolsulfonsaeure-(1-phenyl-ethyl)-ester；1-Phenylethyl 4-methylbenzenesulfonate
• CAS: 6749-54-8
• 化学式: C₁₅H₁₆O₃S
• 分子量: 276.356
• InChiKey: FCRSPZDMYKKCAM-UHFFFAOYSA-N

物化性质

• 沸点：
  412.3±24.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-phenylethyl tosylate 在 二硫化碳 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以96%的产率得到trithiocarbonic acid bis(1-phenylethyl) ester
  参考文献：
  名称：

  An efficient, one-pot synthesis of trithiocarbonates from alcoholic tosylates using the Cs2CO3/CS2 system

  摘要：

  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.

  DOI：

  10.1007/s00706-008-0956-7
• 作为产物：
  描述：

  苏合香醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 1-phenylethyl tosylate
  参考文献：
  名称：

  Nucleophilic substitution reactions of 1-phenylethyl benzenesulfonates with anilines in methanol-acetonitrile

  摘要：

  DOI：

  10.1021/jo00247a004

文献信息

• Regioselective Alkylation of Lithium Dienediolates of α,β-Unsaturated Carboxylic Acids
  作者：Eva M. Brun、Salvador Gil、Ramón Mestres、Margarita Parra

  DOI：10.1055/s-2000-6323

  日期：——

  Lithium carboxylic acids dienediolates are regioselectively alkylated at the α-carbon by reaction with tosylates derived from both primary and secondary alcohols. Both regio- and diastereoselectivity are improved when compared with those obtained in the corresponding alkylation with alkyl halides.

  锂羧酸二烯二醇化物在反应中与由伯醇和仲醇衍生的甲磺酸酯作用，能区域选择性地在α-碳位进行烷基化。与相应的烷基卤代物进行烷基化反应相比，无论是区域选择性还是立体选择性都有所提高。
• Nickel-Catalyzed Reductive Benzylation of Aldehydes with Benzyl Halides and Pseudohalides
  作者：Farhad Panahi、Marzieh Bahmani、Nasser Iranpoor

  DOI：10.1002/adsc.201400970

  日期：2015.4.13

  benzylation of aromatic and aliphatic aldehydes with benzylic halides is reported using a nickel/zinc catalyst system. In addition to benzylic halides, the first report on the addition of benzylic triflates, acetates, tosylates and tritylates to aldehydes is also presented. By this new method a range of alcohols was synthesized efficiently from aldehydes and benzylic substrates at room temperature in moderate

  据报道，使用镍/锌催化剂体系可将芳族和脂族醛与苄基卤化物进行还原性苄基化反应。除苄基卤化物外，还首次报道了向醛中添加苄基三氟甲磺酸酯，乙酸酯，甲苯磺酸酯和三苯甲酸酯的方法。通过这种新方法，可以在室温下从醛和苄基底物中高效合成中度到高产率的多种醇。温和的反应条件和良好的官能团耐受性使这种镍催化的方法可用于合成各种苄醇。
• Nickel-Catalyzed Reductive Etherification of Aldehydes at Room Temperature: C–O vs C–C Bond Formation
  作者：Sajjad Rahimi、Farhad Panahi、Marzieh Bahmani、Nasser Iranpoor

  DOI：10.1021/acs.joc.7b02281

  日期：2018.1.19

  reaction of secondary and tertiary benzyl alcohols activated by 2,4,6-trichloro-1,3,5-triazine (TCT) with aldehydes in the presence of NiCl2·dmg as a precatalyst in ethylene glycol afforded ethers at room temperature. A selective C–O vs C–C bond formation was observed for the secondary and tertiary benzyl alcohols in comparison with primary ones.

  在乙二醇中作为前催化剂的NiCl 2 ·dmg存在下，由2,4,6-三氯-1,3,5-三嗪（TCT）活化的仲和叔苄醇与醛的反应在室温下提供了醚。与伯醇相比，仲和叔苄醇具有选择性的C–O和C–C键形成。
• Reaction of Hydrazones with Methoxy(tosyloxy)iodobenzene (MTIB): Tosylate Formation under Oxidative Conditions
  作者：Christopher Ramsden、Helen Rose

  DOI：10.1055/s-1997-702

  日期：——

  Treatment of aromatic hydrazones 1 containing electron-withdrawing, reduction sensitive substituents with MTIB gives the corresponding tosylates 2 in high yield. When the tosylate is particularly reactive the thermodynamically more stable methyl ether 3 is isolated. Analogous reactions with DAIB give acetates 4 in high yield. Dialkyl hydrazones give olefinic products (e.g. 7 and 8). (+)-Camphor hydrazone 1k with either MTIB or DAIB gives both camphene 12 (major product) and tricyclene 11 (minor product) suggesting that a carbene pathway accounts for some of the material formed in these oxidations.

  含有吸电子、还原敏感取代基的芳香腙1与MTIB反应，可高效地得到相应的甲苯磺酸酯2。当甲苯磺酸酯具有特别高的反应活性时，则会分离得到热力学上更稳定的方式形成的甲醚3。类似地，与DAIB反应可高效地得到乙酸酯4。二烷基腙则生成烯烃产物（例如7和8）。(+)-樟脑腙1k与MTIB或DAIB反应，会同时生成荻烯12（主要产物）和三环烯11（次要产物），表明在这些氧化反应中，卡宾路径可能用于形成一部分反应产物。
• [EN] METAL OXIDE CATALYZED RADIOFLUORINATION<br/>[FR] RADIOFLUORATION CATALYSÉE PAR OXYDE MÉTALLIQUE
  申请人：UNIV CALIFORNIA

  公开号：WO2016004377A1

  公开（公告）日：2016-01-07

  Inter alia, the first titania-catalyzed [18F]-radiofluorination in highly aqueous medium is provided. In embodiments, the method utilizes titanium dioxide, 1 : 1 acetonitrile- thexyl alcohol solvent mixture and tetrabutylammonium bicarbonate as a base. Radiolabeling may be directly performed with aqueous [18F]fluoride without the need for drying/azeotroping step, which reduces radiosynthesis time while keeping high fluoride conversion. The general applicability of the synthetic strategy to the synthesis of the wide range of PET probes from tosylated precursors is demonstrated.

  在此之中，提供了在高度水性介质中进行的第一次钛催化的[18F]-放射氟化反应。在实施例中，该方法利用二氧化钛，1:1的乙腈-己基醇溶剂混合物和四丁基铵碳酸氢盐作为碱。放射标记可以直接使用水性[18F]氟化物进行，无需干燥/共沸步骤，从而减少了放射合成时间，同时保持高氟化物转化率。通过将合成策略普遍应用于从对甲苯磺酸化前体合成各种PET探针的范围，展示了该方法的普适性。