POTASSIUM CYANIDE-13C | 25909-68-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: POTASSIUM CYANIDE-13C
• 英文别名: [¹³C]-potassium cyanide；<13C>potassium cyanide；potassium [1-13C]cyanide；[13C]-potassium cyanide；potassium (13)C-cyanide；[13C]potassium cyanide；[13C]potassuim cyanide
• CAS: 25909-68-6
• 化学式: CKN
• 分子量: 66.105
• InChiKey: YUZRZFQHUCKACF-YTBWXGASSA-N

物化性质

• 熔点：
  >300 °C (lit.)
• 溶解度：
  溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -0.36
• 重原子数：
  3.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

安全信息

• 危险品标志：
  T+,N
• 安全说明：
  S28,S29,S45,S60,S61,S7
• 危险品运输编号：
  UN 1680 6.1/PG 1

反应信息

• 作为反应物：
  描述：

  POTASSIUM CYANIDE-13C 在 磷酸 作用下， 反应 3.0h， 生成 [13C]氰化氢
  参考文献：
  名称：

  Mechanisms of Catalyst Poisoning in Palladium-Catalyzed Cyanation of Haloarenes. Remarkably Facile C−N Bond Activation in the [(Ph₃P)₄Pd]/[Bu₄N]⁺ CN^- System

  摘要：

  Reaction paths leading to palladium catalyst deactivation during cyanation of haloarenes (eq 1) have been identified and studied. Each key step of the catalytic loop (Scheme 1) can be disrupted by excess cyanide, including ArX oxidative addition, X/CN exchange, and ArCN reductive elimination. The catalytic reaction is terminated via the facile formation of inactive [(CN)(4)Pd](2-), [(CN)(3)PdH](2-), and [(CN)(3)PdAr](2-). Moisture is particularly harmful to the catalysis because of facile CN- hydrolysis to HCN that is highly reactive toward Pd(0). Depending on conditions, the reaction of [(Ph3P)(4)Pd] with HCN in the presence of extra CN- can give rise to [(CN)(4)Pd](2-) and/or the remarkably stable new hydride [(CN)(3)PdH](2-) (NMR, X-ray). The X/CN exchange and reductive elimination steps are vulnerable to excess CN- because of facile phosphine displacement leading to stable [(CN)(3)PdAr](2-) that can undergo ArCN reductive elimination only in the absence of extra CN-. When a quaternary ammonium cation such as [Bu4N](+) is used as a phase-transfer agent for the cyanation reaction, C-N bond cleavage in the cation can occur via two different processes. In the presence of trace water, CN- hydrolysis yields HCN that reacts with Pd(0) to give [(CN)(3)PdH)(2-). This also releases highly active OH- that causes Hofmann elimination of [Bu4N](+) to give Bu3N, 1-butene, and water. This decomposition mode is therefore catalytic in H2O. Under anhydrous conditions, the formation of a new species, [(CN)(3)PdBu](2-), is observed, and experimental studies suggest that electron-rich mixed cyano phosphine Pd(0) species are responsible for this unusual reaction. A combination of experimental (kinetics, labeling) and computational studies demonstrate that in this case C-N activation occurs via an S(N)2-type displacement of amine and rule out alternative 3-center C-N oxidative addition or Hofmann elimination processes.

  DOI：

  10.1021/ja078298h

文献信息

• Synthesis and n.m.r.-spectral analysis of unenriched and [1-13C]-enriched 5-deoxypentoses and 5-O-methylpentoses
  作者：Joseph R. Snyder、Anthony S. Serianni

  DOI：10.1016/0008-6215(87)80180-5

  日期：1987.6

  preparing unenriched and [1-13C]-enriched 5-deoxy- and 5-O-methyl-pentoses in the D or L configuration. The 1H-n.m.r. spectra of these compounds have been interpreted, and the 13C-n.m.r. spectra assigned with the aid of 2-D 13C-1H chemical-shift correlation spectroscopy. Tautomeric forms (furanoses, hydrate, and aldehyde) in solution in 2H2O have been quantified with the aid of [1-13C]-enriched derivatives

  描述了用于制备D或L构型的未富集和[1-13C]富集的5-脱氧和5-O-甲基戊糖的化学方法。解释了这些化合物的1H-nmr光谱，并借助2-D 13C-1H化学位移相关光谱法指定了13C-nmr光谱。在2H2O溶液中的互变异构形式（呋喃糖，水合物和醛）已通过富含[1-13C]的衍生物进行了定量。为了评估5-C-脱氧和5-O-甲基化对化学位移和偶联常数（1H-1H，13C- 1H和13C-13C）和戊呋喃糖构象。
• Synthesis of multiply 13C-labeled furofuran lignans using 13C-labeled cinnamyl alcohols as building blocks
  作者：Kati Haajanen、Nigel P. Botting

  DOI：10.1016/j.steroids.2005.10.005

  日期：2006.3

  Plant lignans are currently being widely studied for their potential benefits for human health as their consumption has been correlated with lower risks for developing chronic diseases, such as breast cancer and coronary heart disease. However, studies of some classes of lignans, in particular the furofurans, are hampered by the lack of suitable standards to allow accurate analysis. Herein, we report

  植物木酚素目前正因其对人类健康的潜在益处而被广泛研究，因为它们的消费与患乳腺癌和冠心病等慢性病的风险较低有关。然而，由于缺乏合适的标准来进行准确分析，对某些种类的木脂素，特别是呋喃类的研究受到阻碍。在此，我们报告了两种外消旋 (13)C 标记的呋喃木脂素 [7,8,9-(13)C(3)]medioresinol 和 [7,8,9-(13)C(3)] 芝麻素的合成作为 LC-MS 分析的内标。标记的呋喃木脂素是由三重标记的肉桂醇构建的，使用自由基环化方法。
• Synthesis of [4-13C]-Isoflavonoid Phytoestrogens
  作者：Jacqueline L Whalley、Mark F Oldfield、Nigel P Botting

  DOI：10.1016/s0040-4020(99)01014-5

  日期：2000.1

  Efficient syntheses are described for 13C-labelled derivatives of the isoflavonoid phytoestrogens, genistein, biochanin A, daidzein and formononetin, for use in metabolic studies. The synthetic procedure employs 13C-labelled cyanide as the source of the label to produce the isoflavones with a single 13C atom at the C-4 position.

  描述了用于代谢研究中的13 C标记的异黄酮类植物雌激素，金雀异黄素，生物素A，黄豆苷元和formononetin的有效合成方法。合成程序使用13 C标记的氰化物作为标记的来源，以生产在C-4位置带有单个13 C原子的异黄酮。
• Synthesis and characterisation of13C and15N isotopomers of a 1-acyl-7-nitroindoline
  作者：John E. T. Corrie、Andreas Barth、George Papageorgiou

  DOI：10.1002/jlcr.494

  日期：2001.8

  Efficient methods are described for synthesis of isotopomers of the water-soluble, photolabile 1-acyl-7-nitroindoline 5 with either 13C in the carbonyl of the acyl substituent or 15N in the nitro group. The isotopic incorporations were verified by IR difference spectroscopy coupled with flash photolysis.

  本文描述了合成水溶性、光敏性的1-酰基-7-硝基吲哚5的同位素体的高效方法，其中酰基的羰基位置包含13C，或者硝基位置包含15N。通过红外差谱光谱学结合闪光光解技术验证了同位素的掺入。
• Biosynthesis of the lupine alkaloids. II. Sparteine and lupanine
  作者：W. Marek Golebiewski、Ian D. Spenser

  DOI：10.1139/v88-280

  日期：1988.7.1

  Contrary to predictions based on earlier observations, it is now found that label from DL-[6-¹⁴C]lysine and from [6-¹⁴C]-Δ¹-piperideine does not enter the three C₅ segments of lupanine with equal efficiency. One of the C₅ segments is labelled at a significantly higher level than the other two C₅ segments, which show identical levels of labelling. A new biogenetic model is proposed, which is consistent with these new findings as well as with all other regio- and stereochemical evidence on the mode of incorporation of precursors that is available.

  与基于早期观察的预测相反，现在发现来自DL-[6-¹⁴C]赖氨酸和[6-¹⁴C]-Δ¹-哌啶醛的标记并不以相同效率进入吕植碱的三个C₅片段。其中一个C₅片段的标记水平明显高于另外两个C₅片段，而这两个C₅片段的标记水平相同。提出了一个新的生物合成模型，该模型与这些新发现以及所有其他有关前体物质的结构和立体化学证据的模式的相关性一致。