(3R,4S)-3-ethyl-4,6-diphenyl-1-tosyl-3,4-dihydropyridin-2(1H)-one | 1116670-43-9

• 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: (3R,4S)-3-ethyl-4,6-diphenyl-1-tosyl-3,4-dihydropyridin-2(1H)-one
• 英文别名: (3R,4S)-3-ethyl-1-(4-methylphenyl)sulfonyl-4,6-diphenyl-3,4-dihydropyridin-2-one
• CAS: 1116670-43-9
• 化学式: C₂₆H₂₅NO₃S
• 分子量: 431.555
• InChiKey: INNBAPBGNNPYDG-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-ethyl-4,6-diphenyl-1-tosyl-3,4-dihydropyridin-2(1H)-one 在 2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 对硝基苯酚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (3S,4S)-3-ethyl-4,6-diphenyl-1-tosyl-3,4-dihydropyridin-2(1H)-one
  参考文献：
  名称：

  Organocatalytic Activation of Alkylacetic Esters as Enolate Precursors to React with α,β-Unsaturated Imines

  摘要：

  Asymmetric functionalization of alkylacetic esters and their derivatives is traditionally achieved via preformed enolates with chiral auxiliaries. Catalytic versions of such transformations are attractive but challenging. A direct catalytic activation of simple alkylacetic esters via N-heterocyclic carbene organocatalysts to generate chiral enolate intermediates for highly enantioselective reactions is reported.

  DOI：

  10.1021/ol4021805
• 作为产物：
  描述：

  (2R,3R,4S)-3-ethyl-1-(4-methylphenyl)sulfonyl-4,6-diphenyl-3,4-dihydro-2H-pyridin-2-ol 在 chlorosulfonic-pyridine complex 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以67%的产率得到(3R,4S)-3-ethyl-4,6-diphenyl-1-tosyl-3,4-dihydropyridin-2(1H)-one
  参考文献：
  名称：

  N-磺酰基-1-氮杂-1,3-丁二烯和醛类的有机催化不对称逆电子需求氮杂-Diels-Alder反应。

  摘要：

  DOI：

  10.1002/anie.200804183

文献信息

• An Upstream By-product from Ester Activation via NHC-Catalysis Catalyzes Downstream Sulfonyl Migration Reaction
  作者：Runfeng Han、Liwenze He、Lin Liu、Xingang Xie、Xuegong She

  DOI：10.1002/asia.201500959

  日期：2016.1

  A sequential reaction combining N‐heterocyclic carbene (NHC) and N‐hydroxyphthalimide (NHPI) catalysis allowed for the upstream by‐product NHPI, which was generated in the NHC‐catalyzed cycloaddition reaction, to act as the catalyst for a downstream nitrogen‐to‐carbon sulfonyl migration reaction. Enantiomeric excess of the major product in the cycloaddition reaction remained intact in the follow‐up

  N-杂环卡宾（NHC）和N-羟基邻苯二甲酰亚胺（NHPI）催化相结合的顺序反应允许上游副产物NHPI在NHC催化的环加成反应中生成，充当下游氮到氮的催化剂碳磺酰基迁移反应。在后续的磺酰基迁移反应中，环加成反应中主要产物的对映体过量保持完整。
• Polyhalides as Efficient and Mild Oxidants for Oxidative Carbene Organocatalysis by Radical Processes
  作者：Xingxing Wu、Yuexia Zhang、Yuhuang Wang、Jie Ke、Martin Jeret、Rambabu N. Reddi、Song Yang、Bao-An Song、Yonggui Robin Chi

  DOI：10.1002/anie.201611692

  日期：2017.3.6

  Simple and inexpensive polyhalides (CCl4 and C2Cl6) have been found to be effective and versatile oxidants in removing electrons from Breslow intermediates under N‐heterocyclic carbene (NHC) catalysis. This oxidative reaction involves multiple single‐electron‐transfer (SET) processes and several radical intermediates. The α, β, and γ‐carbon atoms of aldehydes and enals could be readily functionalized

  在N-杂环卡宾（NHC）催化下，简单廉价的多卤化物（CCl 4和C 2 Cl 6）是从布雷斯洛中间体去除电子的有效和通用氧化剂。该氧化反应涉及多个单电子转移（SET）过程和多个自由基中间体。醛和烯醛的α，β和γ-碳原子很容易被官能化。考虑到氧化剂的低成本和反应的广泛适用性，这项研究有望大大提高氧化型NHC催化在大规模应用中的可行性。此外，这种以多卤化物为单电子氧化剂的SET自由基新方法将为NHC催化的自由基反应的发展开辟新的途径。
• Facile Approach for the Oxidative Enolate Activation of Aliphatic Aldehydes
  作者：Qian Liu、Kunpeng Teng

  DOI：10.1021/acs.joc.2c02821

  日期：2023.2.17

  catalytic strategy is developed for the oxidative enolate activation of aliphatic aldehydes. A broad scope of electrophiles including oxindole-derived pyrazolones, oxindole-derived α,β-unsaturated esters, and α,β-unsaturated imines are effective as the reactants in the asymmetric [2 + 4] cycloaddition reaction with the alkyl aldehydes bearing different substitution patterns. Structural complex multicyclic chiral

  开发了一种脯氨酸/N-杂环卡宾中继催化策略，用于脂肪醛的氧化烯醇化活化。包括羟吲哚衍生的吡唑啉酮、羟吲哚衍生的 α,β-不饱和酯和 α,β-不饱和亚胺在内的广泛亲电子试剂在与带有不同取代基的烷基醛的不对称 [2 + 4] 环加成反应中作为反应物是有效的模式。通过这种方法，在相似的反应条件下，结构复杂的多环手性产物通常具有优异的产率和对映和非对映选择性。该协议提供的几种光学纯产品对植物病原体表现出优异的抗菌活性，并有望开发用于植物保护的新型农药。
• 10.1039/d3sc06879j
  作者：Ewing, Paul M. D. A.、Majhi, Pankaj Kumar、Prentice, Callum、Young, Claire M.、van Rees, Karlotta、Arnold, Polly L.、Zysman-Colman, Eli、Smith, Andrew D.

  DOI：10.1039/d3sc06879j

  日期：——

  the NHC-catalysed generation of acyl azolium and azolium enolate intermediates that are of widespread synthetic interest and utility. Treatment of α-phenylthioaldehydes with an NHC precatalyst and base produces an efficient redox rearrangement via a Breslow intermediate, elimination of thiophenolate, and subsequent rebound addition to the generated acyl azolium to give the corresponding thiol ester

  α-苯硫醛可以使用简单的多步骤程序轻松制备，本文中将其作为 NHC 催化生成酰基唑鎓和烯醇化唑鎓中间体的新前体引入，这些中间体具有广泛的合成兴趣和实用性。用 NHC 预催化剂和碱处理 α-苯硫醛，通过Breslow 中间体产生有效的氧化还原重排，消除苯硫酚盐，随后回弹加成至生成的酰基唑鎓，得到相应的硫羟酸酯。在外部醇存在的情况下，氧化还原重排和氧化还原酯化之间的竞争可以通过明智地选择NHC预催化剂内的N-芳基取代基和反应中使用的碱来控制。以NEt 3为基体，带有吸电子（ N -C 6 F 5或N -C 6 H 2 Cl 3 ）取代基的NHC有利于氧化还原重排，而带有富电子N-芳基取代基（ N -Ph, N ）的三唑鎓预催化剂-Mes) 导致优先氧化还原酯化。使用DBU时，由于最初形成的硫羟酸酯产物发生酯交换反应，因此优选氧化还原酯化反应。此外，α-苯硫醛衍生的唑鎓烯醇化物已用于对映选择性形式[4
• Organocatalytic Activation of Alkylacetic Esters as Enolate Precursors to React with α,β-Unsaturated Imines
  作者：Lin Hao、Shaojin Chen、Jianfeng Xu、Bhoopendra Tiwari、Zhenqian Fu、Tong Li、Jieyan Lim、Yonggui Robin Chi

  DOI：10.1021/ol4021805

  日期：2013.10.4

  Asymmetric functionalization of alkylacetic esters and their derivatives is traditionally achieved via preformed enolates with chiral auxiliaries. Catalytic versions of such transformations are attractive but challenging. A direct catalytic activation of simple alkylacetic esters via N-heterocyclic carbene organocatalysts to generate chiral enolate intermediates for highly enantioselective reactions is reported.