2-hydroxybenzonitrile sodium salt | 74255-21-3

• 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-hydroxybenzonitrile sodium salt
• 英文别名: sodium 2-hydroxybenzonitrile；salicylonitrile sodium salt；2-cyanophenol sodium salt；sodium 2-cyanophenolate；sodium o-cyanophenoxide；sodium;2-cyanophenolate
• CAS: 74255-21-3
• 化学式: C₇H₄NO*Na
• 分子量: 141.105
• InChiKey: DRBWSICLBVQNAQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.36
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxybenzonitrile sodium salt 在 samarium diiodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙腈 为溶剂， 反应 6.0h， 生成 邻羟基苯甲腈
  参考文献：
  名称：

  Cyclizations and Rearrangements of Samarium Diiodide-Generated Vinyl Radicals

  摘要：

  Vinyl bromides 1, 5, 15, 20, 23, 27, 33a,b, 41a-c, 44a-c, 46a,b, 52a,b, 55a, 56a,b, and 60a,b react with samarium diiodide in THF and/or acetonitrile to give the corresponding vinyl radicals. Radicals 3, 7, and 16 afforded products deriving from cyclization on the adjacent triple bond in a 5-(pi-exo)exo, 6-(pi-endo)exo, and 6-(pi-exo)exo mode, respectively. Radical 7 undergoes competitive 1,5-hydrogen translocation. Vinyl radicals 21 and 24 readily cyclize on the proximal double bond, leading to 5- and 6-membered rings, respectively. Thienyl-substituted radical 28 leads to a product deriving from 5-exo cyclization on the thiophene ring and subsequent beta-fission of the C-S bond, whereas thienyl-substituted radicals 34a,b undergo almost exclusively 1,5-hydrogen translocation. Aryl-substituted radicals obtained from vinyl bromides 41, 44, 46, 52, and 55 do not form any products deriving from 5-exo or 6-exo cyclization (or ipso cyclization). Finally, naphthyl-substituted radicals 57a and 61a give only direct reduction products, whereas the radical 61b affords, in addition to the direct reduction product, a rearranged product deriving from a 1,3-radical migration of the naphthylthio group. Evidence is reported for the reduction of EWG-substituted benzene rings and thio-substituted naphthalene rings to radical anions, which can fragment on the side chain with the elimination of allyl radicals. alpha-Oxy(and alpha-thio)-substituted radicals deriving from 1,5-shift rearrange to alcohols (and thiols) through a Wittig rearrangement or a cyclization/fragmentation process.

  DOI：

  10.1021/jo00128a013
• 作为产物：
  描述：

  水杨醛肟 在 氢氧化钾 、 sodium hydroxide 、 硫酸 作用下， 以 水 为溶剂， 生成 2-hydroxybenzonitrile sodium salt
  参考文献：
  名称：

  Spectrochemical, ab initio and density functional studies on the conversion of 2-hydroxybenzonitrile (o-cyanophenol) into the oxyanion

  摘要：

  The spectral and structural changes caused by the conversion of 2-hydroxybenzonitrile (o-cyanophenol) into the corresponding oxyanion have been followed by IR spectra, ab initio and density functional force field calculations. In agreement between theory and experiment, the conversion is accompanied by a 29 cm(-1) frequency decrease of the cyano stretching band, 2.7-fold increase in its integrated intensity, 5.8-fold (total value) intensification of the aromatic skeletal bands of Wilson's 8 and 19 types, and other essential spectral changes. According to the calculations, the strongest structural changes are the shortening of the Ph-O bond with 0.10 Angstrom, lengthenings of the adjacent CC bonds in the phenylene ring with 0.06 Angstrom and bond angle variations near the oxyanionic center. All these changes are connected with the formation of a quasi-ortho-quinonoidal structure of the o-phenylene ring in the oxyanion. According to the electronic density analysis, 0.41 e(-) (Mulliken) or 0.56 e(-) (natural bond orbital, NBO) of the anionic charge remain localized at the oxyanionic center. Conformations and hydrogen bonds have also been discussed on the basis of experimental and theoretical data. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2003.12.040

文献信息

• 嘧菌酯的合成方法
  申请人：重庆紫光国际化工有限责任公司

  公开号：CN104230822B

  公开（公告）日：2017-03-08

  本发明公开了一种嘧菌酯的合成方法，包括在碱性条件，催化剂存在下，4,6‑二氯嘧啶和2‑(2‑羟基苯基)‑3,3‑二甲氧基丙酸甲酯在合适的溶剂中进行偶联反应得到2‑[2‑(6‑氯嘧啶‑4‑基氧基)苯基]‑3,3‑二甲氧基丙酸甲酯；加入2‑羟基苯甲腈和碱或者2‑羟基苯甲腈的盐，反应得到2‑[2‑[6‑(2‑氰基苯氧基)嘧啶‑4‑基氧基]苯基]‑3,3‑二甲氧基丙酸甲酯；脱去一分子甲醇得到嘧菌酯。或者将反应得到的2‑[2‑(6‑氯嘧啶‑4‑基氧基)苯基]‑3,3‑二甲氧基丙酸甲酯先脱去一分子甲醇，然后与2‑羟基苯甲腈和碱或者2‑羟基苯甲腈的盐反应得到嘧菌酯。本发明使用新设计的催化剂，简化分离及后处理过程，适应大规模工业化生产。
• Synthesis of Functionalized 1H-Pyrazolo[4,3-e][1,2,4]triazines and Their Fused Derivatives via Ipso-Substitution of Methylsulfonyl Group with O-, N-, S- and C-Nucleophiles
  作者：Andrzej Rykowski、Mariusz Mojzych

  DOI：10.3987/com-04-10108

  日期：——

  reaction of 3-methyl-5-methylsulfonyl-1-phenyl-1H-pyrazolo[4,3-e][1,2,4]triazine (4) with a range of C-, N-, O- and S-nucleophiles afforded the corresponding substitution products (5a-m) in high yields. The reaction of 5-hydrazino compound (5m) with carboxylic acids furnished 1H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-b][1,2,4]triazines (8a) and (8b).

  3-甲基-5-甲基磺酰基-1-苯基-1H-吡唑并[4,3-e][1,2,4]三嗪(4)与一系列C-、N-、O-的同位取代反应和 S- 亲核试剂以高产率提供相应的取代产物 (5a-m)。5-肼基化合物 (5m) 与羧酸反应得到 1H-吡唑并[4,3-e]-1,2,4-三唑并[4,3-b][1,2,4]三嗪 (8a) (8b)。
• Plakhtinskii, V. V.; Ustinov, V. A.; Ryabukhina, N. S., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 3, p. 507 - 509
  作者：Plakhtinskii, V. V.、Ustinov, V. A.、Ryabukhina, N. S.、Mironov, G. S.、Kaninskii, P. S.

  DOI：——

  日期：——
• Viti, Giovanni; Giannotti, Danilo; Nannicini, Rossano, Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1369 - 1375
  作者：Viti, Giovanni、Giannotti, Danilo、Nannicini, Rossano、Ricci, Renzo、Pestillini, Vittorio

  DOI：——

  日期：——
• 1,2,4-triazines in organic synthesis. 8. Intramolecular diels-alder reaction of 5-acyl-1,2,4-triazineoxime ethers. New route of synthesis of alkylhetarylketones
  作者：T. Lipińska、D. Branowska、A. Rykowski

  DOI：10.1007/bf02259365

  日期：1999.3