N-(2-hydroxy-2-(p-tolyl)ethyl)-4-methylbenzenesulfonamide | 502878-46-8

• 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: N-(2-hydroxy-2-(p-tolyl)ethyl)-4-methylbenzenesulfonamide
• 英文别名: N-[2-hydroxy-2-(4-methylphenyl)ethyl]-4-methylbenzenesulfonamide
• CAS: 502878-46-8
• 化学式: C₁₆H₁₉NO₃S
• 分子量: 305.398
• InChiKey: WZDCBLOLNLSGTD-UHFFFAOYSA-N

物化性质

• 沸点：
  496.4±55.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-2-(p-tolyl)ethyl)-4-methylbenzenesulfonamide 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 36.33h， 生成 2-(p-tolyl)-4-tosyl-6-vinylmorpholine 、 2-(p-tolyl)-4-tosyl-6-vinylmorpholine
  参考文献：
  名称：

  N系链烷醇的非对映选择性合成取代的吗啉：（±）-Chelonin A的全合成

  摘要：

  氯化钯催化的氮系链烷醇的分子内环化反应可产生高产的吗啉。该方法用于（±）-chelonin A的全合成。

  DOI：

  10.1021/acs.joc.6b02260
• 作为产物：
  描述：

  1-(4-methylphenyl)-2-nitroethanol 在 甲醇 、 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 反应 0.5h， 生成 N-(2-hydroxy-2-(p-tolyl)ethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  手性Organotin催化的氨基氨基醇的动力学拆分。

  摘要：

  用手性锡催化剂首次获得了外消旋氨基醇的高效动力学拆分。在联萘骨架的3,3'-位置具有3,4,5-三氟苯基的手性有机锡化合物可实现出色的收率和高对映选择性，从而实现这种转化。该方法可耐受芳基和烷基取代的氨基醇以及多种其他底物，从而以高对映选择性和高达> 500的因子提供相应的产物。

  DOI：

  10.1002/anie.201909700

文献信息

• ENZYME-CATALYZED ENANTIOSELECTIVE AZIRIDINATION OF OLEFINS
  申请人：California Institute of Technology

  公开号：US20160222423A1

  公开（公告）日：2016-08-04

  The present invention provides methods for catalyzing the conversion of an olefin to a compound containing one or more aziridine functional groups using heme enzymes. In certain aspects, the present invention provides a reaction mixture for producing an aziridination product, the reaction mixture comprising of an olefinic substrate, a nitrene precursor, and a heme enzyme. In other certain aspects, the present invention provides a method for producing an aziridination product comprising providing an olefinic substrate, a nitrene precursor, and a heme enzyme; and admixing the components in a reaction for a time sufficient to produce an aziridine product. In other aspects, the present invention provides heme enzymes including variants and fragments thereof that are capable of carrying out in vivo and in vitro olefin aziridination reactions. Expression vectors and host cells expressing the heme enzymes are also provided by the present invention.

  本发明提供了利用血红素酶催化烯烃转化为含有一个或多个氮杂环丙烷官能团的化合物的方法。在某些方面，本发明提供了用于生产氮杂环丙烷产物的反应混合物，该反应混合物包括烯烃底物、氮烯前体和血红素酶。在其他某些方面，本发明提供了一种生产氮杂环丙烷产物的方法，包括提供烯烃底物、氮烯前体和血红素酶；并将这些组分混合在反应中，以产生氮杂环丙烷产物所需的时间。在其他方面，本发明提供了包括能够在体内和体外进行烯烃氮杂环丙烷化反应的血红素酶及其变体和片段。本发明还提供了表达载体和表达血红素酶的宿主细胞。
• Synthesis of aminoalcohols from substituted alkenes <i>via</i> tungstenooxaziridine catalysis
  作者：Rufai Madiu、Brandon Dellosso、Erin L. Doran、Jenna M. Doran、Ali A. Pinarci、Tyler M. TenHoeve、Amari M. Howard、James L. Stroud、Dominic A. Rivera、Dylan A. Moskovitz、Steven J. Finneran、Alyssa N. Singer、Morgan E. Rossi、Gustavo Moura-Letts

  DOI：10.1039/d4ob00022f

  日期：——

  stereospecificity. A catalytic cycle involving the formation of tungstenooxaziridine complex 1 as the active catalyst and hydrolysis of tungstenooxazolidine intermediate A as the rate-determining-step has been proposed. Initial kinetic and competition experiments provide evidence for the proposed mechanism.

  在此，我们报道了使用磺酰胺作为N​​的定量来源的WO 2 Dipic(H 2 O)促进的烯烃氧胺化。该反应适用于活化和未活化的烯烃，具有高产率、非对映选择性和立体特异性。提出了一种催化循环，涉及作为活性催化剂的钨恶氮丙啶配合物1的形成和作为限速步骤的钨恶唑烷中间体A的水解。初始动力学和竞争实验为所提出的机制提供了证据。
• NaHSO3-Promoted Ring Openings of N-Tosylaziridines and Epoxides with H2O
  作者：Wen-Long Wei、Xing Li、Bin Ni、Hong-Hong Chang

  DOI：10.3987/com-13-12885

  日期：——

  NaHSO3-oriented ring openings of a wide variety of N-tosylaziridines and epoxides with H2O under mild conditions in acetone was found to be a convenient and effective method, which provided the desired beta-aminoalcohols and beta-diols in good to excellent yields and with uniformly high regioselectivity.
• <i>cis</i>-1,2-Aminohydroxylation of Alkenes Involving a Catalytic Cycle of Osmium(III) and Osmium(V) Centers: Os^V(O)(NHTs) Active Oxidant with a Macrocyclic Tetradentate Ligand
  作者：Hideki Sugimoto、Akine Mikami、Kenichiro Kai、P. K. Sajith、Yoshihito Shiota、Kazunari Yoshizawa、Kaori Asano、Takeyuki Suzuki、Shinobu Itoh

  DOI：10.1021/acs.inorgchem.5b01083

  日期：2015.7.20

  Catalytic activity of [Os-III(OH)(H2O)(L-N4Me2)](PF6)(2) (1: L-N4Me2 = N,N'-dimethyl-2,11-diaza-[3,3](2,6)pyridinophane) in 1,2-cis-aminohydroxylation of alkenes with sodium N-chloro-4-methylbenzenesulfonamide (chloramine-T) is explored. Simple alkenes as well as those containing several types of substituents are converted to the corresponding 1,2-aminoalcohols in modest to high yields. The aminoalcohol products have exclusively cis conformation with respect to the introduced -OH and -NHTs groups. The spectroscopic measurements including cold mass spectroscopic study of the reaction product of complex 1 and chloromine-T as well as density functional theory (DFT) calculations indicate that an oxido-aminato-osmium(V) species [Os-V(O)(NHTs)(L-N4Me2)](PF6)(2) (2) is an active oxidant for the aminohydroxylation. The DFT calculations further indicate that the reaction involves a [3 + 2] cycloaddition between 2 and alkene, and the regioselectivity in the aminohydroxylation of unsymmetrical alkenes is determined by the orientation that bears less steric hindrance from the tosylamino group, which leads to the energetically more preferred product isomer.
• Wang, Yan; Zhang, Ming Jie; Zhu, Jie, Journal of the Indian Chemical Society, 2011, vol. 88, # 9, p. 1367 - 1370
  作者：Wang, Yan、Zhang, Ming Jie、Zhu, Jie、Li, Zhong Bo

  DOI：——

  日期：——