N-(naphthalen-1-yl)-3-phenyl-1,2,4-thiadiazol-5-amine | 330153-94-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(naphthalen-1-yl)-3-phenyl-1,2,4-thiadiazol-5-amine
• 英文别名: N-naphthalen-1-yl-3-phenyl-1,2,4-thiadiazol-5-amine
• CAS: 330153-94-1
• 化学式: C₁₈H₁₃N₃S
• 分子量: 303.387
• InChiKey: UBPVXPIUUOCKGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(naphthalen-1-yl)-3-phenyl-1,2,4-thiadiazol-5-amine 、 copper(II) bis(trifluoromethanesulfonate) 以 乙酸乙酯 为溶剂， 生成 Cu(3-phenyl-5-(1-aminonaphthyl)-1,2,4-thiadiazole)⁽²⁺⁾
  参考文献：
  名称：

  Cu(II)- and Hg(II)-Induced Modulation of the Fluorescence Behavior of a Redox-Active Sensor Molecule

  摘要：

  Here, we report on a fluorescent 1,2,4-thiadiazole derivative (oxidized form) and its reduced form, the corresponding iminoyl thiourea. The thiadiazole displays a strong modulation of its fluorescence behavior, selectively upon addition of Cu(II), while the iminoyl thiourea functions as a chemodosimeter for Hg(II). Additionally, the Cu(II)-thiadiazole complex is characterized by HRMS, and the HE(II)-induced desulfurization of the iminoyl thiourea is monitored by mass spectrometry.

  DOI：

  10.1021/ic000827u
• 作为产物：
  描述：

  N-iminobenzyl-N'-(αnaphthyl)-thiourea 在 tetrabutylammonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 以85%的产率得到N-(naphthalen-1-yl)-3-phenyl-1,2,4-thiadiazol-5-amine
  参考文献：
  名称：

  电化学氧化分子内NS键的形成：3-取代的5-氨基-1,2,4-噻二唑的合成。

  摘要：

  通过亚氨基硫基脲的电氧化分子内脱氢NS键的形成，已经开发了一种简便而有效的合成3-取代的5-氨基-1,2,4-噻二唑的方法。在室温下在无催化剂和无氧化剂的电解条件下，合成了各种1,2,4-噻二唑衍生物，具有良好的收率和优异的收率，具有广泛的底物范围和出色的官能团耐受性。

  DOI：

  10.1021/acs.joc.9b03155

文献信息

• Transition-metal-free S–N bond formation: synthesis of 5-amino-1,2,4-thiadiazoles from isothiocyanates and amidines
  作者：Zan Yang、Ting Cao、Si Liu、An Li、Kun Liu、Tao Yang、Congshan Zhou

  DOI：10.1039/c9nj01419e

  日期：——

  has been developed by the reaction of isothiocyanates with amidines. This protocol which is free of metal, catalyst and iodine involves O2 oxidative S–N bond formation for the synthesis of various 5-amino-1,2,4-thiadiazole derivatives with excellent to good yields. High regioselectivity, mild reaction conditions, broad substrate scope and good functional group tolerance are the highlights of the report

  通过异硫氰酸酯与am的反应，已经开发出一种新颖的绿色合成5-氨基-1,2,4-噻二唑的方法。该方案不含金属，催化剂和碘，涉及O 2氧化S–N键的形成，可用于合成各种5-氨基-1,2,4-噻二唑衍生物，并具有优异的收率。高区域选择性，温和的反应条件，广泛的底物范围和良好的官能团耐受性是该报告的重点。
• Electrochemical Oxidative Intramolecular N–S Bond Formation: Synthesis of 3-Substituted 5-Amino-1,2,4-Thiadiazoles
  作者：Zan Yang、Jiaqi Zhang、Liping Hu、Lijun Li、Kun Liu、Tao Yang、Congshan Zhou

  DOI：10.1021/acs.joc.9b03155

  日期：2020.3.6

  A facile and efficient protocol for the synthesis of 3-substituted 5-amino-1,2,4-thiadiazoles has been developed through the electro-oxidative intramolecular dehydrogenative N-S bond formation of imidoyl thioureas. Various 1,2,4-thiadiazole derivatives were synthesized in good to excellent yields with broad substrate scope and excellent functional group tolerance under catalyst- and oxidant-free electrolytic

  通过亚氨基硫基脲的电氧化分子内脱氢NS键的形成，已经开发了一种简便而有效的合成3-取代的5-氨基-1,2,4-噻二唑的方法。在室温下在无催化剂和无氧化剂的电解条件下，合成了各种1,2,4-噻二唑衍生物，具有良好的收率和优异的收率，具有广泛的底物范围和出色的官能团耐受性。
• Cu(II)- and Hg(II)-Induced Modulation of the Fluorescence Behavior of a Redox-Active Sensor Molecule
  作者：Gunther Hennrich、Wolfgang Walther、Ute Resch-Genger、Helmut Sonnenschein

  DOI：10.1021/ic000827u

  日期：2001.2.1

  Here, we report on a fluorescent 1,2,4-thiadiazole derivative (oxidized form) and its reduced form, the corresponding iminoyl thiourea. The thiadiazole displays a strong modulation of its fluorescence behavior, selectively upon addition of Cu(II), while the iminoyl thiourea functions as a chemodosimeter for Hg(II). Additionally, the Cu(II)-thiadiazole complex is characterized by HRMS, and the HE(II)-induced desulfurization of the iminoyl thiourea is monitored by mass spectrometry.