N-(2-chloro-2-phenylethyl)tosylamide | 17798-13-9

• 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-(2-chloro-2-phenylethyl)tosylamide
• 英文别名: N-(2-chloro-2-phenylethyl)-4-methylbenzenesulfonamide；2-chloro-2-phenyl-N-tosylethanamine
• CAS: 17798-13-9
• 化学式: C₁₅H₁₆ClNO₂S
• 分子量: 309.817
• InChiKey: KWMYKUZVSMQPMT-UHFFFAOYSA-N

物化性质

• 熔点：
  137 °C
• 沸点：
  456.2±55.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-chloro-2-phenylethyl)tosylamide 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium cyanoborohydride 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 以99%的产率得到4-甲基-N-(2-苯基乙基)苯磺酰胺
  参考文献：
  名称：

  BF₃·OEt₂-Mediated Highly Regioselective S_N2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides

  摘要：

  A highly regioselective Lewis acid-mediated S(N)2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH2Cl2 solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed. The mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines with excellent er and dr. Chloroamines obtained from 2,3-disubstituted aziridines were converted to the chiral N-tosylamines via radical dehalogenation.

  DOI：

  10.1021/jo902244y
• 作为产物：
  描述：

  1-[[(4-甲基苯基)磺酰基]氨基]-吡啶鎓氢氧化物内盐 在 (4,4'-二叔丁基-2,2'-联吡啶)双[(2-吡啶基)苯基]铱(III)六氟磷酸盐 、 吡啶盐酸盐 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.5h， 生成 N-(2-chloro-2-phenylethyl)tosylamide
  参考文献：
  名称：

  通过光氧化还原催化烯烃的区域特异性三组分氨基氟化

  摘要：

  已经开发了具有高区域选择性的直接可见光介导的苯乙烯氨基氟化。将耐贮存的N -Ts保护的1-氨基吡啶盐用作氮自由基前体，并将可商购的氟化氢-吡啶用作亲核氟化物源。进行LY503430类似物的合成以证明该策略的合成价值。

  DOI：

  10.1021/acs.orglett.8b01760

文献信息

• A phosphonium ylide as a visible light organophotoredox catalyst
  作者：Yasunori Toda、Katsumi Tanaka、Riki Matsuda、Tomoyuki Sakamoto、Shiho Katsumi、Masahiro Shimizu、Fuyuki Ito、Hiroyuki Suga

  DOI：10.1039/d1cc00996f

  日期：——

  A phosphonium ylide-based visible light organophotoredox catalyst has been designed and successfully applied to halohydrin synthesis using trichloroacetonitrile and epoxides. An oxidative quenching cycle by the ylide catalyst was established, which was confirmed by experimental mechanistic studies.

  已经设计了基于磷鎓叶立德的可见光有机光氧化还原催化剂，并成功地将其应用于使用三氯乙腈和环氧化物的卤代醇合成中。建立了由叶立德催化剂的氧化猝灭循环，这已通过实验机理研究得到证实。
• Rasta resin–triphenylphosphine oxides and their use as recyclable heterogeneous reagent precursors in halogenation reactions
  作者：Xuanshu Xia、Patrick H Toy

  DOI：10.3762/bjoc.10.143

  日期：——

  Heterogeneous polymer-supported triphenylphosphine oxides based on the rasta resin architecture have been synthesized, and applied as reagent precursors in a wide range of halogenation reactions. The rasta resin–triphenylphosphine oxides were reacted with either oxalyl chloride or oxalyl bromide to form the corresponding halophosphonium salts, and these in turn were reacted with alcohols, aldehydes, aziridines and epoxides to form halogenated products in high yields after simple purification. The polymer-supported triphenylphosphine oxides formed as a byproduct during these reactions could be recovered and reused numerous times with no appreciable decrease in reactivity.

  基于RASTA树脂架构的异质聚合物支承的氧化三苯基膦已经被合成，并应用于广泛的卤化反应中作为试剂前体。RASTA树脂-氧化三苯基膦与草酰氯或草酰溴反应，形成相应的卤化膦盐，这些卤化膦盐再与醇、醛、氮杂环丙烷和环氧乙烷反应，在简单纯化后以高收率形成卤代产物。在这些反应中形成的聚合物支承的氧化三苯基膦作为副产品，可以被回收并多次重复使用，且没有明显的活性下降。
• Regio- and Stereoselective Ring Opening of Epoxides and Aziridines Using Zirconyl Chloride: An Efficient Approach for the Synthesis of β-Chlorohydrins and β-Chloroamines
  作者：Biswanath Das、Maddeboina Krishnaiah、Katta Venkateswarlu

  DOI：10.1246/cl.2007.82

  日期：2007.1

  Zirconyl chloride mediated regio- and stereoselective ring opening of epoxides and aziridines at room temperature affords the corresponding β-chlorohydrins and β-chloroamines, respectively in high yields.

  在室温下，通过氯锆酸锆催化的环氧化物和氮杂环丙烷的区域选择性和立体选择性开环反应，分别以高产率得到相应的β-氯醇和β-氯胺。
• A Versatile Metal-Free Intermolecular Aminochlorination of Alkenes
  作者：Claudio Martínez、Kilian Muñiz

  DOI：10.1002/adsc.201300880

  日期：2014.1.13

  New reaction conditions for the rapid and productive intermolecular aminochlorination reaction of alkenes using a combination of chloramine‐T and a Brønstedt acid are described. Upon simple protonation of chloramine‐T, conditions for a mild and selective aminochlorination are obtained. In addition, the reaction can proceed to form either of the two possible regioisomers, depending on whether a stoichiometric

  描述了使用氯胺-T和布朗斯台德酸的组合快速而有效地进行烯烃分子间氨基氯化反应的新反应条件。对氯胺-T进行简单质子化后，即可获得轻度和选择性氨基氯化的条件。另外，取决于是否使用化学计量的这种酸活化剂或乙酸，反应可以继续以形成两种可能的区域异构体中的任一种。该反应对所有不同种类的烯烃均有效。总共提供了50多个示例来说明此概念。
• Synthesis of N-sulfonyl aziridines through regioselective opening of epoxides under solid-liquid PTC conditions
  作者：Domenico Albanese、Dario Landini、Michele Penso、Silvia Petricci

  DOI：10.1016/s0040-4020(99)00214-8

  日期：1999.5

  The ring opening of epoxides 1 with 4-toluenesulfonamide (6) under solid-liquid phase transfer catalysis (SL-PTC) conditions afforded regioselectively β-sulfonamidoalcohols 7 in high yields. These were further converted into N-sulfonylaziridines 9 after activation of the hydroxy leaving group followed by ring closing in the presence of potassium carbonate.

  在固体-液相转移催化（SL-PTC）条件下，环氧化物1与4-甲苯磺酰胺（6）的开环以高产率提供了区域选择性的β-磺酰胺基醇7。在羟基离去基团活化后，将它们进一步转化为N-磺酰基氮丙啶9，然后在碳酸钾存在下闭环。