(R)-fipronil | 302578-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (R)-fipronil
• 英文别名: (-)-fipronil；5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(R)-trifluoromethylsulfinyl]pyrazole-3-carbonitrile
• CAS: 302578-97-8
• 化学式: C₁₂H₄Cl₂F₆N₄OS
• 分子量: 437.152
• InChiKey: ZOCSXAVNDGMNBV-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  氟虫腈 在 amylose tris(3-chloro-5-methylphenylcarbamate) immobilized on 3 μm porous spherical silica particles 作用下， 以 水 、 乙腈 为溶剂， 生成 (S)-fipronil 、 (R)-fipronil
  参考文献：
  名称：

  杀虫剂氟虫腈对映体的手性拆分及其主要转化产物的高效液相色谱-质谱联用测定

  摘要：

  使用基于直链淀粉三（3-氯-5-甲基苯基氨基甲酸酯）的手性柱开发了一种高效液相色谱-质谱（HPLC-MS）方法，用于分析氟虫腈（一种流行的杀虫神经毒剂）和相关的转化产物. 优化后的方法达到了单次同时完全分离多种氟虫腈的目标，包括氟虫腈对映体、氟虫腈代谢物和光产物的手性分离。这种方法的有效性通过其在分析暴露于阳光条件下的一系列氟虫腈样品中的应用得到证明。笼统，

  DOI：

  10.1002/chir.23412

文献信息

• Development of New HPLC Chiral Stationary Phases Based on Native and Derivatized Cyclofructans
  作者：Ping Sun、Chunlei Wang、Zachary S. Breitbach、Ying Zhang、Daniel W. Armstrong

  DOI：10.1021/ac902257a

  日期：2009.12.15

  An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic- and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromatic-functionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high “loadability” and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents.

  首次引入一类不寻常的手性选择剂——环糊精作为键合型手性固定相。与天然环糊精（CFs）相比，其作为手性选择剂的能力相当有限，而脂族和芳族功能化的CF6具有独特且截然不同的对映体选择性。事实上，它们能够分离非常广泛的消旋化合物。特别是，低取代度的脂族衍生化CF6能够基线分离所有测试的手性伯胺。似乎部分衍生化作用于CF6分子会破坏分子内部的氢键，从而使分子核心更易接近。相比之下，高度芳族功能化的CF6固定相在伯胺的对映选择能力方面丧失了大部分能力，但它们对大多数其他类型的分析物获得了广泛的选择性。这类固定相还表现出高“负荷能力”，因此具有在制备分离方面的巨大潜力。对映体选择性的变化通常可以与选择剂的独特结构特征相关联。分离主要在有机溶剂存在下发生。
• Intermediates for pesticidal composition comprising enantiomeric form of fipronil
  申请人：——

  公开号：US20020082289A1

  公开（公告）日：2002-06-27

  A compound having the formula: 1 wherein E is an organic radical which is enantiomerically enriched.

  具有以下式子的化合物 1 其中 E 是对映体富集的有机基。
• [EN] COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR DES CYCLOFRUCTANES EN TANT QU'AGENTS DE SÉPARATION
  申请人：UNIV TEXAS

  公开号：WO2010148191A3

  公开（公告）日：2011-05-19
• Enantioselective Chronic Toxicity of Fipronil to Ceriodaphnia dubia
  作者：W. Aaron Wilson、Brad J. Konwick、Arthur W. Garrison、Jimmy K. Avants、Marsha C. Black

  DOI：10.1007/s00244-007-9003-7

  日期：2008.1

  Fipronil is a phenylpyrazole pesticide that has greatly increased in popularity in recent years. As a chiral molecule, fipronil is released into the environment as a 1:1 mixture (called a racemate) of its two enantiomers. Previous toxicity work has indicated that the enantiomers of fipronil exhibit significantly different levels of acute toxicity to the nontarget organism Ceriodaphnia dubia. In this work we examine the chronic effects of the pure enantiomers and racemate on the survival, development, mobility, and reproduction of C. dubia adults and the survival and mobility of their offspring. Based on 8-day trials, the (+) enantiomer of fipronil showed a significantly greater reduction in the number of offspring (LOEC = 2 mu g/L) than either the racemate (LOEC = 15 mu g/L) or the (-) enantiomer (LOEC = 30 mu g/L). The (+) enantiomer was also shown to be significantly more toxic to neonates born during the course of the experiment (LC50(24) = 18.1 mu g/L, LC50(48) = 10.3 mu g/L) than the racemate (LC50(24) = 33.3 mu g/L, LC50(48) = 30.3 mu g/L), but only after 48 h. Both the (+) enantiomer and the racemate were significantly more toxic to C. dubia than the (-) enantiomer (LC50(24) = 65.2 mu g/L, LC50(48) = 50.1 mu g/L) at both time points. Qualitative mobility data followed a similar trend, with the (+) enantiomer causing greater impairment in mobility at low concentrations. These data imply that the (-) enantiomer has less impact on the reproductive success of C. dubia than either the (+) enantiomer or the racemate. Enantiomerically pure or enriched formulations of (-) fipronil may reduce impacts to the nontarget organism C. dubia.
• (S)-ENANTIOMER ENRICHED FIPRONIL COMPOSITION
  申请人：MERIAL

  公开号：EP1168920B1

  公开（公告）日：2003-06-18