2-sulfanylidene-N-(3,4,5-trimethoxyphenyl)-1H-pyridine-3-carboxamide | 1061770-30-6

• 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: 2-sulfanylidene-N-(3,4,5-trimethoxyphenyl)-1H-pyridine-3-carboxamide
• CAS: 1061770-30-6
• 化学式: C₁₅H₁₆N₂O₄S
• 分子量: 320.369
• InChiKey: BFVPGGBXEMGZGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-二氯硝基苯 、 2-sulfanylidene-N-(3,4,5-trimethoxyphenyl)-1H-pyridine-3-carboxamide 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以76%的产率得到9-nitro-6-(3,4,5-trimethoxyphenyl)benzo[b]pyrido[3,2-f]-[1,4]thiazepin-5(6H)-one
  参考文献：
  名称：

  Transition Metal-Free One-Pot Synthesis of Fused 1,4-Thiazepin-5(4H)-ones and Theoretical Study of the S–N Type Smiles Rearrangement Process

  摘要：

  A series of 1,4-thiazepin-5(4H)-one derivatives were synthesized via a transition metal-free one-pot Smiles rearrangement process at room temperature. Regioselective seven-membered heterocycles were constructed in good to excellent yields. To gain an in-depth understanding of the S-N type Smiles rearrangement mechanism, a theoretical study was also performed by quantum chemistry calculations.

  DOI：

  10.1021/jo5011729

文献信息

• A transition metal-free tandem process to pyridazinopyrido[3,2-f][1,4]thiazepine-diones via Smiles rearrangement
  作者：Xiaoyi Niu、Bingchuan Yang、Yanqiu Li、Shuai Fang、Zixiao Huang、Caixia Xie、Chen Ma

  DOI：10.1039/c3ob40719e

  日期：——

  A transition metal-free methodology for the synthesis of pyridazinopyrido[3,2-f][1,4]thiazepine-diones was studied. The construction of this tricyclic system went through a one-pot coupling/Smiles rearrangement/cyclization process. The high yields of pure products were obtained through simple recrystallization.

  研究了一种合成哒嗪并吡啶并[3,2-f][1,4]硫氮杂卓二酮的无过渡金属方法。该三环体系的构建是通过一锅耦合/斯迈尔斯重排/环化过程完成的。通过简单的重结晶获得了高产率的纯产品。