N-[(4-chloro-3-nitrophenyl)methylidene]-4-methylbenzenesulfonamide | 1020855-43-9

• 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: N-[(4-chloro-3-nitrophenyl)methylidene]-4-methylbenzenesulfonamide
• CAS: 1020855-43-9
• 化学式: C₁₄H₁₁ClN₂O₄S
• 分子量: 338.771
• InChiKey: DBUKAYRZNZHXMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(4-chloro-3-nitrophenyl)methylidene]-4-methylbenzenesulfonamide 、 3-苯基丙炔腈 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以14%的产率得到6-(4-chloro-3-nitrophenyl)-2,4-diphenyl-1-tosyl-1,2-dihydropyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  高度区域选择性膦促进的 [2+2+2] 氰基乙炔和 N-甲苯磺酰亚胺环化成 1,2-二氢吡啶-3,5-二甲腈衍生物

  摘要：

  在叔膦存在下，通过氰基乙炔和 N-甲苯磺酰亚胺的 [2+2+2] 环化，可以轻松制备一系列全功能化的二氢吡啶-3,5-二甲腈衍生物。研究了环化反应的范围，并通过合理的反应机理解释了高区域选择性。

  DOI：

  10.1055/s-0037-1610708
• 作为产物：
  描述：

  对甲苯磺酰胺 、 4-氯-3-硝基苯甲醛 在 amberlyst 作用下， 以 甲苯 为溶剂， 生成 N-[(4-chloro-3-nitrophenyl)methylidene]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  用于组装三氟甲基硫醇 (SCF3) 氮丙啶和环丙烷结构的温和 Darzens 环化

  摘要：

  我们通过 Darzens 启发的协议报告了三取代三氟甲基硫醇化 (SCF 3 ) 氮丙啶和环丙烷的温和新环化方法。这些阴离子环化的产物，以前很少研究，具有吸引人的特征，使它们成为合成平台的宝贵构建块。在这项研究中，显示在其 α 位置带有 SCF 3和溴取代基的三取代苯乙酮亲核试剂在温和的反应条件下与乙烯基酮和甲苯磺酰基保护的亚胺进行 [2 + 1] 环化。

  DOI：

  10.1021/acs.orglett.1c02204

文献信息

• One-pot formation of fluorescent γ-lactams having an α-phosphorus ylide moiety through three-component α(δ′)-Michael reactions of phosphines with an enyne and N-tosyl aldimines
  作者：Yu-Wei Lin、Jie-Cheng Deng、You-Zung Hsieh、Shih-Ching Chuang

  DOI：10.1039/c3ob41811a

  日期：——

  We demonstrate a straightforward synthesis of γ-lactams possessing an α-phosphorus ylide moiety from assembly of phosphines, N-tosyl aldimines and an enyne through an initial α(δ′)-attack of phosphines to an enyne in up to 79% yield. The investigated multicomponent reaction tolerates a variety of triarylphosphines and electron-poor aldimines to give γ-lactams in one pot. One of the lactams, with the tri(p-tol)phosphine and 4-cyanophenyl moiety, exhibits fluorescence emission at 447 nm with a quantum yield of 0.11.

  我们展示了一种简单的合成方法，通过初始的α(δ')-攻击，利用磷、N-托烯基醛亚胺和烯炔的组合，合成具有α-磷耦基的γ-内酰胺，产率高达79%。所研究的多组分反应耐受多种三芳基磷和电子贫乏的醛亚胺，能在一个反应体系中生成γ-内酰胺。其中一种内酰胺，含有三(对甲基)磷和4-氰基苯基团，在447 nm处表现出荧光发射，量子产率为0.11。
• Visible Light Organo‐Photocatalytic Synthesis of 3‐Imidazolines
  作者：Poornima Mishra、Ipsha Shruti、Ruchir Kant、Tejender S. Thakur、Akhilesh Kumar、Namrata Rastogi

  DOI：10.1002/ejoc.202201079

  日期：2022.11.25

  An efficient synthesis of tetrasubstituted 3-imidazolines under organo-photocatalytic conditions has been developed through formal [3+2]-cycloaddition between 2H-azirines and N-tosyl benzylidene imines. While the reaction exhibited complete regiocontrol, products were obtained as separable mixture of cis (major) and trans (minor) diastereoisomers in most of the cases.

  通过 2 H-氮杂环丙烷和N-甲苯磺酰亚苄基亚胺之间的形式 [3+2]-环加成，开发了在有机光催化条件下有效合成四取代 3-咪唑啉的方法。虽然反应表现出完全的区域控制，但在大多数情况下，产物作为顺式（主要）和反式（次要）非对映异构体的可分离混合物获得。
• Cycloaddition of Alkynyl Ketones with <i>N</i>-Tosylimines Catalyzed by Bu₃P and DMAP: Synthesis of Highly Functionalized Pyrrolidines and Azetidines
  作者：Ling-Guo Meng、Peijie Cai、Qingxiang Guo、Song Xue

  DOI：10.1021/jo801687v

  日期：2008.11.7

  Cycloadditions of alkynyl ketones with N-tosylimines catalyzed by Lewis bases to synthesize azetidines and pyrrolidines were systematically described. In the reaction of alkynyl ketones with N-tosylimines catalyzed by Bu3P at room temperature in toluene, highly functionalized pyrrolidines were formed in good to excellent yields. When DMAP was used in place of Bu3P as catalyst to facilitate the cycloaddition, completely substituted azetidines were produced in moderate to good yields in CH2Cl2. Both cyclization reactions proceeded smoothly with complete stereoselectivity. The scope and limitations of these cycloadditon reactions were also investigated.
• Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF₃) Aziridine and Cyclopropane Structures
  作者：Michael D. Delost、Jon T. Njardarson

  DOI：10.1021/acs.orglett.1c02204

  日期：2021.8.6

  We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents

  我们通过 Darzens 启发的协议报告了三取代三氟甲基硫醇化 (SCF 3 ) 氮丙啶和环丙烷的温和新环化方法。这些阴离子环化的产物，以前很少研究，具有吸引人的特征，使它们成为合成平台的宝贵构建块。在这项研究中，显示在其 α 位置带有 SCF 3和溴取代基的三取代苯乙酮亲核试剂在温和的反应条件下与乙烯基酮和甲苯磺酰基保护的亚胺进行 [2 + 1] 环化。
• Highly Regioselective Phosphine-Promoted [2+2+2] Annulations of Cyanoacetylenes and N-Tosylimines to 1,2-Dihydropyridine-3,5-dicarbonitrile Derivatives
  作者：Jinfeng Zhang、Qi Zhang、Xin Ji、Ling-Guo Meng

  DOI：10.1055/s-0037-1610708

  日期：2019.6

  A series of fully functionalized dihydropyridine-3,5-dicarbonitrile derivatives were easily prepared through [2+2+2] annulations of cyanoacetylenes and N-tosylimines in the presence of tertiary phosphine. The scope of the cyclization reaction was investigated, and the high regioselectivity was explained by a rational reaction mechanism.

  在叔膦存在下，通过氰基乙炔和 N-甲苯磺酰亚胺的 [2+2+2] 环化，可以轻松制备一系列全功能化的二氢吡啶-3,5-二甲腈衍生物。研究了环化反应的范围，并通过合理的反应机理解释了高区域选择性。