(±)-N-(4-methoxybenzylidene)-p-toluenesulfinamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (±)-N-(4-methoxybenzylidene)-p-toluenesulfinamide
• 英文别名: N-[(4-methoxyphenyl)methylidene]-4-methylbenzenesulfinamide
• 化学式: C₁₅H₁₅NO₂S
• 分子量: 273.356
• InChiKey: WUMBSVXGWAXNSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sodium 4-methylbenzenesulfinate 在 iron(III) chloride 、 草酰氯 、 阻聚剂701 、 L-缬氨酸 、 氧气 作用下， 以 甲苯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 (±)-N-(4-methoxybenzylidene)-p-toluenesulfinamide
  参考文献：
  名称：

  通过醇与亚磺酰胺或磺酰胺的氧化级联反应，Fe(III)/l-缬氨酸催化一锅法合成 N-亚磺酰基-和 N-磺酰亚胺

  摘要：

  发现了一种有效的 Fe(III)、l-缬氨酸和 4-OH-TEMPO 催化体系，用于醇的氧化，然后在一个锅中与亚磺酰胺或磺酰胺缩合，合成 N-亚磺酰基-和 N-磺酰亚胺化合物。条件温和。这种转变适用于各种底物，显示出高官能团耐受性，并以良好到优异的产率提供相应的产品。

  DOI：

  10.1055/s-0037-1609320

文献信息

• Direct synthesis of N-sulfinyl- and N-sulfonylimines via copper/<scp>l</scp>-proline-catalyzed aerobic oxidative cascade reaction of alcohols with sulfinamides or sulfonamides
  作者：Guofu Zhang、Shengjun Xu、Xiaoqiang Xie、Chengrong Ding、Shang Shan

  DOI：10.1039/c6ra26490e

  日期：——

  An efficient one-pot synthetic method of N-sulfinyl- and N-sulfonylimines by the condensation of alcohols with sulfinamides or sulfonamides under mild and green conditions has been developed using a combination of CuI, L-proline and TEMPO. This system shows excellent functional group compatibility for a wide range of substrates and affords the corresponding products in good to excellent yields.

  通过使用CuI，L-脯氨酸和TEMPO的组合，开发了一种通过在温和绿色条件下使醇与亚磺酰胺或磺酰胺缩合来合成N-亚磺酰基和N-磺酰亚胺的有效一锅法。该系统对多种底物均显示出优异的官能团相容性，并以良好至极好的收率提供了相应的产品。
• A General Aminocatalytic Method for the Synthesis of Aldimines
  作者：Sara Morales、Fernando G. Guijarro、José Luis García Ruano、M. Belén Cid

  DOI：10.1021/ja4111418

  日期：2014.1.22

  A general and efficient biomimetic method for the synthesis of aldimines from aldehydes and compounds bearing the NH2 group in the presence of pyrrolidine as a catalyst has been developed. These organocatalytic reactions, based on the application of the concept of nucleophilic catalysis, proceed with outstanding yields in the absence of acids and metals under simple conditions and minimum experimental manipulation. The method has been mainly applied to the synthesis of N-sulfinyl and N-sulfonyl imines, but its general validity has been proven with the preparation of representative N-phosphinoyl, N-alkyl, and N-aryl imines. These unprecedented reactions, which presumably occur via iminium activation without requiring acidic conditions, are an interesting and competitive alternative to the classical methods for preparing aldimines.