N-(2-氯-1-苯基乙基)-4-甲基苯磺酰胺 | 17798-15-1

• 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: N-(2-氯-1-苯基乙基)-4-甲基苯磺酰胺
• 英文名称: N-(2-chloro-1-phenylethyl)-4-methylbenzenesulfonamide
• 英文别名: Benzenesulfonamide, N-(2-chloro-1-phenylethyl)-4-methyl-
• CAS: 17798-15-1
• 化学式: C₁₅H₁₆ClNO₂S
• mdl: MFCD01131634
• 分子量: 309.817
• InChiKey: JCIHMVMXJDYETN-UHFFFAOYSA-N

物化性质

• 熔点：
  167-167.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  456.3±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

• 作为产物：
  描述：

  苯乙烯 、 chloroamine-T 在 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以84%的产率得到N-(2-氯-1-苯基乙基)-4-甲基苯磺酰胺
  参考文献：
  名称：

  A One-Pot β-Chloro-N′-tosylamidination of Olefins with Chloramine-T

  摘要：

  介绍了一种利用氯胺-T 和三氟甲磺酸从烯烃直接合成 δ-氯-N′-对甲苯磺酸酰胺的新方法。

  DOI：

  10.1055/s-0030-1260021

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。
• 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。
• Indium Trihalide Mediated Regioselective Ring Opening of Aziridines: A Facile Synthesis of 2-Haloamines
  作者：J. S. Yadav、B. V. Subba Reddy、G. Mahesh Kumar

  DOI：10.1055/s-2001-16775

  日期：——

  A variety of N-tosyl aziridines undergo ring opening with indium trihalides in acetonitrile at ambient temperature to afford the corresponding haloamines in excellent yields with high regioselectivity.

  多种 N-甲苯磺酰基氮丙啶在环境温度下与乙腈中的三卤化铟开环，以优异的收率和高区域选择性得到相应的卤代胺。
• Use of trichloroacetonitrile as a hydrogen chloride generator for ring-opening reactions of aziridines
  作者：Yasunori Toda、Riki Matsuda、Shuto Gomyou、Hiroyuki Suga

  DOI：10.1039/c9ob00602h

  日期：——

  Regioselective ring-opening reactions of 2-aryl-N-tosylaziridines are described, in which hydrogen chloride is generated by photodegradation of trichloroacetonitrile. HCl adducts are obtained in high yields in 1,4-dioxane, whereas methanol adducts are predominantly obtained in methanol. Trichloroacetonitrile can serve as a photoresponsive molecular storage generator for hydrogen chloride.

  描述了2-芳基-N-甲苯磺酰基氮丙啶的区域选择性开环反应，其中通过三氯乙腈的光降解产生氯化氢。在1,4-二恶烷中可以高收率获得HCl加合物，而在甲醇中则主要获得甲醇加合物。三氯乙腈可以用作氯化氢的光敏分子存储生成器。
• Catalytic Asymmetric Chloroamination Reaction of α,β-Unsaturated γ-Keto Esters and Chalcones
  作者：Yunfei Cai、Xiaohua Liu、Jun Jiang、Weiliang Chen、Lili Lin、Xiaoming Feng

  DOI：10.1021/ja110668c

  日期：2011.4.20

  Highly efficient catalytic chloroamination reaction of alpha,beta-unsaturated gamma-keto esters and chalcones has been developed via a chloronium-based mechanism to deliver anti-regioselective vicinal chloroamines instead of the aziridinium intermediates delivered aminochlorides. The combination of TsNCl2 and TsNH2 as reagents made the transformation highly efficient, delivering the gamma-carbonyl-beta-chloro-alpha-amino acid derivatives and alpha-chloro-beta-amino-ketone derivatives in nearly quantitative yields with up to 99% ee and 99:1 dr under 0.05-0.5 mol % catalyst loading. TsNHCl was demonstrated to act as the key reactive species to form a bridged chloronium ion intermediate in the presence of a chiral scandium complex. The method might provide useful information for further realization of other haloamination reactions.