naphthalene-2-carboxamidrazone | 96984-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalene-2-carboxamidrazone
• 英文别名: [2]naphthamidrazone；[2]Naphthamidrazon；β-Naphthoesaeure-imid-hydrazid；β-Naphthoesaeure-amidrazon；N'-aminonaphthalene-2-carboximidamide
• CAS: 96984-72-4
• 化学式: C₁₁H₁₁N₃
• 分子量: 185.228
• InChiKey: DHCQAKNDCYVKRC-UHFFFAOYSA-N

物化性质

• 沸点：
  346.9±25.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  naphthalene-2-carboxamidrazone 以 乙醇 为溶剂， 生成 bis-(amino-[2]naphthyl-methylene)-hydrazine
  参考文献：
  名称：

  Ried,W.; Schomann,P., Justus Liebigs Annalen der Chemie, 1967, vol. 701, p. 92 - 100

  摘要：

  DOI：
• 作为产物：
  描述：

  2-萘甲腈 生成 naphthalene-2-carboxamidrazone
  参考文献：
  名称：

  Kauffmann,T. et al., Angewandte Chemie, 1963, vol. 75, p. 344

  摘要：

  DOI：

文献信息

• Synthesis of 5-aryl-3-C-glycosyl- and unsymmetrical 3,5-diaryl-1,2,4-triazoles from alkylidene-amidrazones
  作者：Béla Szőcs、Éva Bokor、Katalin E. Szabó、Attila Kiss-Szikszai、Marietta Tóth、László Somsák

  DOI：10.1039/c5ra05702g

  日期：——

  Bromination of the so obtained compounds by NBS gave hydrazonoyl bromide type derivatives which were ring closed to 3-C-glycosyl-5-substituted-1,2,4-triazoles in pyridine or by NH4OAc in AcOH. Under the same conditions O-perbenzoylated N1-arylidene-C-(β-D-glucopyranosyl)-formamidrazones gave the expected 1,2,4-triazoles as minor products only. N1-Arylidene-arenecarboxamidrazones were also transformed

  在具有多种生物活性的1,2,4-三唑衍生物中，3 - C-吡喃葡萄糖基-5-取代的1,2,4-三唑属于糖原磷酸化酶的最有效抑制剂，因此是潜在的降糖药。在寻找用于这类化合物的新的合成方法中，研究了N 1-亚烷基羧酰胺dra的氧化性闭环。在NaH 2 PO 2存在下，通过Raney-Ni®还原反应，由相应的糖基氰化物和酰氨基prepared酰胺制备O-酰化的N 1-（β- D-甘氨酸金烷基糖基亚甲基）-芳族羧酰胺基酮。通过NBS对如此获得的化合物进行溴化得到了酰肼基溴化物型衍生物，其在吡啶中或在AcOH中通过NH 4 OAc与3- C-糖基-5-取代-1,2,4-三唑闭环。在相同条件下ø -perbenzoylated Ñ 1 -arylidene- Ç - （β- d吡喃葡萄糖基）-formamidrazones给出预期的-1,2,4-三唑作为只有轻微的产品。N 1-亚芳基-亚芳基甲酰胺还与NBS
• Kauffmann,T. et al., Angewandte Chemie, 1963, vol. 75, p. 344
  作者：Kauffmann,T. et al.

  DOI：——

  日期：——
• Pinner, Chemische Berichte, 1897, vol. 30, p. 1877
  作者：Pinner

  DOI：——

  日期：——
• Ried,W.; Schomann,P., Justus Liebigs Annalen der Chemie, 1968, vol. 714, p. 122 - 127
  作者：Ried,W.、Schomann,P.

  DOI：——

  日期：——
• C-(β-d-Glucopyranosyl)formamidrazones, formic acid hydrazides and their transformations into 3-(β-d-glucopyranosyl)-5-substituted-1,2,4-triazoles: a synthetic and computational study
  作者：Éva Bokor、Attila Fekete、Gergely Varga、Béla Szőcs、Katalin Czifrák、István Komáromi、László Somsák

  DOI：10.1016/j.tet.2013.09.099

  日期：2013.12

  Synthesis of O-perbenzoylated 3-(beta-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, precursors of potent inhibitors of glycogen phosphorylase, was studied by ring closures of N-1-acyl-carboxamidrazone type intermediates. Reactions of C-(beta-D-glucopyranosyl)formimidate or C-(beta-D-glucopyranosyl)formamidine with acid hydrazides as well as acylation of C-(beta-D-glucopyranosyl)formamidrazone by acid chlorides unexpectedly gave the corresponding 1,3,4-oxadiazoles instead of 1,2,4-triazoles. The desired triazoles were obtained in reactions of C-(beta-D-glucopyranosyl)formamidine or C-(beta-D-glucopyranosyl) formyl chloride with arenecarboxamidrazones, and also in acylations of N-1-tosyl-C-(beta-D-glucopyranosyl)formamidrazone with acid chlorides. Theoretical calculations (B3LYP and M06-2X OFT with the standard 6-31G(d,p) basis set) on simple model compounds with methyl and phenyl substituents to understand the bifurcation of the ring closure of N-1-acyl-carboxamidrazones indicated that in general the reaction led to 1,2,4-triazoles. However, the probability of the 1,3,4-oxadiazole forming pathway was shown to be significantly higher with N-1-benzoyl-acetamidrazones, which were closest analogues of the intermediates resulting in C-glucosyl-1,3,4-oxadiazoles. It was thereby demonstrated that the substitution pattern of the N-1-acyl-carboxamidrazones played a fundamental role in determining the direction of the ring closing reaction. (C) 2013 Elsevier Ltd. All rights reserved.