N-(2-hydroxy-2-(naphthalen-2-yl)ethyl)-4-methylbenzenesulfonamide | 952571-98-1

• 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-(naphthalen-2-yl)ethyl)-4-methylbenzenesulfonamide
• 英文别名: N-(2-hydroxy-2-naphthalen-2-ylethyl)-4-methylbenzenesulfonamide
• CAS: 952571-98-1
• 化学式: C₁₉H₁₉NO₃S
• 分子量: 341.431
• InChiKey: VFAFZVIAVYEFEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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-(naphthalen-2-yl)ethyl)-4-methylbenzenesulfonamide 、 苯甲酰氯 在 (S)-4,4-dibromo-2,6-bis(3,4,5-trifluorophenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]stannepine 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以48%的产率得到(S)-2-((4-methylphenyl)sulfonamido)-1-(naphthalen-2-yl)ethyl benzoate
  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
• 作为产物：
  描述：

  N-(4-tolylsulfonyl)-2-(2-naphthyl)aziridine 在 水 、 sodium hydrogensulfite 作用下， 以 丙酮 为溶剂， 反应 21.0h， 以83%的产率得到N-(2-hydroxy-2-(naphthalen-2-yl)ethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  NaHSO3-Promoted Ring Openings of N-Tosylaziridines and Epoxides with H2O

  摘要：

  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.

  DOI：

  10.3987/com-13-12885

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。
• A tandem process for the synthesis of β-aminoboronic acids from aziridines with haloamine intermediates
  作者：Subin Park、Jangwoo Koo、Weonjeong Kim、Hong Geun Lee

  DOI：10.1039/d2cc00808d

  日期：——

  An unprecedented synthetic strategy is devised to generate β-aminoboronic acids from aziridines via a sequential process involving 1,2-iodoamine formation and radical borylation under light irradiation. A variety of aziridines including multiply substituted aziridines have been successfully employed as synthetic precursors, expanding their synthetic utility compared to previous methods. Mechanistic

  设计了一种前所未有的合成策略，通过涉及在光照射下形成 1,2-碘胺和自由基硼化的顺序过程从氮丙啶生成 β-氨基硼酸。包括多重取代的氮丙啶在内的多种氮丙啶已成功用作合成前体，与以前的方法相比，它们的合成效用得到了扩展。机理研究表明，硼源在硼化步骤和卤胺中间体的形成中起着独特的作用。
• 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.
• Chiral‐Organotin‐Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
  作者：Hui Yang、Wen‐Hua Zheng

  DOI：10.1002/anie.201909700

  日期：2019.11.4

  A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3'-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of

  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。