N-(4-cyanobenzyl)-N,4-dimethylbenzenesulfonamide | 70539-48-9

• 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-cyanobenzyl)-N,4-dimethylbenzenesulfonamide
• 英文别名: N-[(4-cyanophenyl)methyl]-N,4-dimethylbenzenesulfonamide
• CAS: 70539-48-9
• 化学式: C₁₆H₁₆N₂O₂S
• 分子量: 300.381
• InChiKey: ILTHDOHEEMZHAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-cyanobenzyl)-N,4-dimethylbenzenesulfonamide 在 氢氧化钾 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 生成 4-[[Methyl-(4-methylphenyl)sulfonylamino]methyl]benzoyl chloride
  参考文献：
  名称：

  Analogs of methotrexate

  摘要：

  Analogues of methotrexate (MTX) were prepared by alkylation of side-chain precursors with 6-(bromomethyl)-2,4-pteridinediamine followed, where necessary, by saponification of the intermediate esters and, in two cases, by electrophilic substitution reactions in the pyridine ring portion of 3-deazamethotrexate. Effects of the various modifications on their ability to inhibit dihydrofolate reductase, cytotoxicity, and activity against L1210 leukemia in mice were examined in light of recent findings concerning active transport of MTX and related compounds and the binding features of the MTX-dihydrofolate reductase complex.

  DOI：

  10.1021/jm00193a021
• 作为产物：
  描述：

  N-甲基-4-氰基苄胺 、 sodium 4-methylbenzenesulfinate 在 copper(ll) bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以89%的产率得到N-(4-cyanobenzyl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  Copper-catalyzed sulfonamides formation from sodium sulfinates and amines

  摘要：

  报道了一种通过铜催化的氧化耦合反应，利用亚磺酸钠和胺在1大气压氧气或二甲基亚砜作为氧化剂的条件下构建磺酰胺的新型便捷方法。该方法提供了高效且稳健的功能性磺酰胺合成途径，产率高且化学选择性极佳。详细的机理研究表明，这一转化过程可能通过单电子转移（SET）途径进行。

  DOI：

  10.1039/c3cc41249k

文献信息

• Copper-catalyzed sulfonamides formation from sodium sulfinates and amines
  作者：Xiaodong Tang、Liangbin Huang、Chaorong Qi、Xia Wu、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c3cc41249k

  日期：——

  A new and convenient method for the construction of sulfonamides via a copper-catalyzed oxidative coupling between sodium sulfinates and amines with 1 atm O2 or DMSO as the oxidant was described. This method provides efficient and robust synthesis of functional sulfonamides in good yields and excellent chemoselectivity. And detailed mechanistic studies showed that this transformation may go through a single electron transfer (SET) pathway.

  报道了一种通过铜催化的氧化耦合反应，利用亚磺酸钠和胺在1大气压氧气或二甲基亚砜作为氧化剂的条件下构建磺酰胺的新型便捷方法。该方法提供了高效且稳健的功能性磺酰胺合成途径，产率高且化学选择性极佳。详细的机理研究表明，这一转化过程可能通过单电子转移（SET）途径进行。
• Analogs of methotrexate
  作者：John A. Montgomery、James R. Piper、Robert D. Elliott、Carroll Temple、Eugene C. Roberts、Y. F. Shealy

  DOI：10.1021/jm00193a021

  日期：1979.7

  Analogues of methotrexate (MTX) were prepared by alkylation of side-chain precursors with 6-(bromomethyl)-2,4-pteridinediamine followed, where necessary, by saponification of the intermediate esters and, in two cases, by electrophilic substitution reactions in the pyridine ring portion of 3-deazamethotrexate. Effects of the various modifications on their ability to inhibit dihydrofolate reductase, cytotoxicity, and activity against L1210 leukemia in mice were examined in light of recent findings concerning active transport of MTX and related compounds and the binding features of the MTX-dihydrofolate reductase complex.