10-formyl-9-methylanthracene oxime | 119826-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10-formyl-9-methylanthracene oxime
• 英文别名: 10-methyl-9-anthracenecarbaldehyde oxime；10-methyl-anthracene-9-carbaldehyde-oxime；10-Methyl-anthracen-9-carbaldehyd-oxim；(NE)-N-[(10-methylanthracen-9-yl)methylidene]hydroxylamine
• CAS: 119826-85-6
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: HKSMHIRWJFWLMG-LICLKQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  10-formyl-9-methylanthracene oxime 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 4.42h， 生成 9-(10-bromomethyl) cyanoanthracene
  参考文献：
  名称：

  New Synthetic Amino Acids for the Design and Synthesis of Peptide-Based Metal Ion Sensors

  摘要：

  The syntheses of two new nonstandard amino acids, Flu (6) and YBp (20), and a new synthesis of Dmd (12) are reported. These residues exhibit fluorescence, metal-coordination, and fluorescence-quenching properties, respectively. These building blocks have been incorporated into peptides via solid phase peptide synthesis to afford the prototype fur a photoinduced electron transfer-based metal ion chemosensor. The fluorescence of the peptides is modulated upon metal binding. This results from a metal. ion-induced conformational change that brings the side chains of the Flu and Dmd amino acids into proximity, thereby favoring photoinduced electron transfer (PET) fluorescence quenching.

  DOI：

  10.1021/jo961466w
• 作为产物：
  描述：

  10-甲基蒽-9-甲醛 在 羟胺 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 10-formyl-9-methylanthracene oxime
  参考文献：
  名称：

  New Synthetic Amino Acids for the Design and Synthesis of Peptide-Based Metal Ion Sensors

  摘要：

  The syntheses of two new nonstandard amino acids, Flu (6) and YBp (20), and a new synthesis of Dmd (12) are reported. These residues exhibit fluorescence, metal-coordination, and fluorescence-quenching properties, respectively. These building blocks have been incorporated into peptides via solid phase peptide synthesis to afford the prototype fur a photoinduced electron transfer-based metal ion chemosensor. The fluorescence of the peptides is modulated upon metal binding. This results from a metal. ion-induced conformational change that brings the side chains of the Flu and Dmd amino acids into proximity, thereby favoring photoinduced electron transfer (PET) fluorescence quenching.

  DOI：

  10.1021/jo961466w

文献信息

• Synthesis and Properties of Dinitromethylated Arenes. Reinvestigation of the Ponzio Reaction
  作者：Hitomi Suzuki、Hiroshi Takaoka、Hidetoshi Yamamoto、Takuji Ogawa

  DOI：10.1246/bcsj.61.2927

  日期：1988.8

  Several title compounds have been prepared by the modified Ponzio procedure and their IR, 1H and 13C NMR data are presented. In some cases trinitromethylated arenes were obtained as a by-product. Oxidative cleavage to parent aldehydes and oxidation to carboxylic acids were the major competing reactions. 9-Anthracenecarbaldehyde oxime and 10-methyl-9-anthracenecarbaldehyde oxime reacted with nitrogen

  几种标题化合物已通过改进的 Ponzio 程序制备，并提供了它们的 IR、1H 和 13C NMR 数据。在某些情况下，三硝基甲基化芳烃作为副产物获得。氧化裂解为母体醛和氧化为羧酸是主要的竞争反应。9-蒽甲醛肟和10-甲基-9-蒽甲醛肟以意想不到的方式与二氧化氮反应，得到10-硝基-9-蒽甲腈氧化物和10-甲基-10-硝基-9-蒽酮作为各自的主要产物。（二硝基甲基）苯的硝化也已在各种条件下进行了检查。
• Homolytic bond dissociation energies of the acidic carbon-hydrogen bonds in .alpha.-substituted and 10-substituted 9-methylanthracenes and their related radical anions
  作者：Xian Man Zhang、Frederick G. Bordwell、Joseph E. Bares、Jin Pei Cheng、Brian C. Petrie

  DOI：10.1021/jo00063a025

  日期：1993.5

  Equilibrium acidities (pK(HA)), reduction potentials E(re)(HA), oxidation potentials E(ox)(HA), and oxidation potentials of the conjugate anions E(ox)(A-) have been measured in dimethylsulfoxide(DMSO) solution for 13 alpha-substituted 9-methylanthracenes (9-GCH2An) and 11 10-substituted 9-methylanthracenes (10-G-9-MeAn). The equilibrium acidities have been shown to be linearly correlated with Hammett sigma- constants. The similar rho- values for the linear correlations of pK(HA) Vs sigma- for 9-GCH2An (rho- = 13.8) and 10-G-9-MeAn (rho- = 14.2) demonstrate that the like substituents in 9-GCH2An and 10-G-9-MeAn have similar large effects on the equilibrium acidities. Suitable combinations of these equilibrium acidities with the reduction and oxidation potentials led to estimates of (a) the homolytic bond dissociation energies (BDE(HA)) of the acidic C-H bonds in 9-GCH2An and 10-G-9-MeAn, (b) the homolytic bond dissociation energies (BDE(HA.-)) of the acidic C-H bonds in 9-GCH2An.- and 10-G-9-MeAn.- radical anions, and (c) the radical cation acidities (pK(HA.+)) of the 9-GCH2An.+ and 10-G-9-MeAn.+ radical cations. Introduction of alpha-CN and alpha-NO2 groups had opposite effects on the strengths (BDE(HA)) of the acidic C-H bonds in 9-GCH2An; the alpha-CN group decreased the BDE(HA) value by 2.5 kcal/mol and the alpha-NO2 increased the BDE(HA) value by 4.5 kcal/mol, but they both weakened the acidic C-H bonds in 9-GCH2An.- radical anions (by 10.6 and 12.5 kcal/mol, respectively). The BDEs of the acidic C-H bonds in 10-G-9-MeAn were estimated to be 81.3 +/- 1.3 kcal/mol and those in the corresponding radical anions were estimated to be 58.5 +/- 2.5 kcal/mol. The 9-GCH2An.+ and 10-G-9-MeAn.+ radical cations are strongly acidic with the pK(HA.+) values estimated in the range of -5 to -11 pK(HA.+) units. Seven linear free energy relationships have been observed.
• The N-Methylformanilide Synthesis of Aldehydes
  作者：Louis F. Fieser、J. Elmore Jones

  DOI：10.1021/ja01259a055

  日期：1942.7
• Abnormal Beckmann Rearrangement of 9,10-Dihydro-9,10-(11-ketoethano)anthracene Oxime¹
  作者：S. WAWZONEK、J. V. HALLUM

  DOI：10.1021/jo01085a022

  日期：1959.3
• Polar radicals. 16. Comments on a recently published mechanistic study of photobromination using bromotrichloromethane
  作者：Dennis D. Tanner、Edward V. Blackburn、Darwin W. Reed、B. P. Setiloane

  DOI：10.1021/jo01313a032

  日期：1980.12