(R)-苄氟噻嗪 | 1087345-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 中文名称: (R)-苄氟噻嗪
• 英文名称: (R)-bendroflumethiazide
• 英文别名: bendroflumethiazide；(3R)-3-benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide
• CAS: 1087345-31-0
• 化学式: C₁₅H₁₄F₃N₃O₄S₂
• 分子量: 421.421
• InChiKey: HDWIHXWEUNVBIY-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  苄氟噻嗪 在 uridine bonded to silica gel 作用下， 以 正己烷 、 异丙醇 、 三氟乙酸 为溶剂， 生成 (R)-苄氟噻嗪 、 (S)-苄氟噻嗪
  参考文献：
  名称：

  Uridine, Thymidine and Inosine Used as Chiral Stationary Phases in HPLC

  摘要：

  本文中，我们首次报道了利用胸苷、尿苷和次黄嘌呤作为手性固定相，通过3-(三乙氧基硅基)丙基异氰酸酯键合到硅胶上的高效液相色谱法对手性分离的研究。胸苷和尿苷手性固定相在正相和反相模式下具有对醇类、胺类、酮类和羧酸类化合物一定程度的手性分离选择性。这一工作表明，核苷或脱氧核苷可作为液相色谱中分离对映体的一种新型手性固定相。

  DOI：

  10.14233/ajchem.2014.15674

文献信息

• Enantioselective potential of polysaccharide-based chiral stationary phases in supercritical fluid chromatography
  作者：Gabriela Kucerova、Kveta Kalikova、Eva Tesarova

  DOI：10.1002/chir.22701

  日期：2017.6

  cellulose‐based chiral stationary phase were achieved particularly with propane‐2‐ol and a mixture of isopropylamine and trifluoroacetic acid as organic modifier and additive to CO2, respectively. Methanol and basic additive isopropylamine were preferred on amylose‐based chiral stationary phase. The complementary enantioselectivity of the cellulose‐ and amylose‐based chiral stationary phases allows separation

  使用一组52种分析物在超临界流体色谱中评估了两种基于多糖的手性固定相对手性结构多样的生物活性化合物的对映选择性。固定在2.5μm二氧化硅颗粒上的手性选择剂是纤维素或直链淀粉的三（3,5-二甲基苯基carmabate）衍生物。监测了多糖主链，不同的有机改性剂和不同的流动相添加剂对保留和对映体分离的影响。对于大多数化合物，发现了快速基线对映体分离的条件。纤维素基手性固定相的基线和部分对映体分离的成功率分别为51.9％和15.4％。使用基于直链淀粉的手性固定相，我们获得了76。被测化合物的基线对映体分离率为9％，部分对映体分离率为9.6％。尤其是使用丙烷-2-醇以及异丙胺和三氟乙酸的混合物作为有机改性剂和CO添加剂时，在基于纤维素的手性固定相上获得了最佳结果2个。在基于直链淀粉的手性固定相上，优选甲醇和碱性添加剂异丙胺。纤维素和直链淀粉基手性固定相的互补对映选择性可分离大多数经测试的结构不同的化
• 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。
• Investigation into the performance and stability of immobilized and coated polysaccharide columns in supercritical fluid chromatography
  作者：Lei Yue、Madeline Yeh、John Reilly、Bing Wang、Christopher J. Welch、Maria Phan

  DOI：10.1002/chir.23626

  日期：2024.1

  In this study, the performance of the widely used “golden four” coated chiral stationary phases (Chiralpak AD‐3, Chiralcel OD‐3, Chiralpak AS‐3, and Chiralcel OJ‐3) was compared with their corresponding immobilized versions (Chiralpak IA‐3, Chiralpak IB‐3, Chiralpak IB N‐3, Chiralpak IH‐3, and Chiralpak IJ‐3) under supercritical fluid chromatography (SFC) conditions with a set of 30 racemic compounds. Using the traditional modifiers, methanol and isopropanol, the immobilized columns (Chiralpak IB N‐3 and Chiralpak IH‐3) showed an improved general ability to successfully resolve the enantiomers of the target analytes relative to their coated versions (Chiralcel OD‐3 and Chiralpak AS‐3), while the coated columns (Chiralpak AD‐3, Chiralcel OD‐3, and Chiralcel OJ‐3) performed better than their immobilized versions (Chiralpak IA‐3, Chiralpak IB‐3, and Chiralpak IJ‐3). An investigation of the non‐traditional modifiers, dichloromethane, ethyl acetate, and tetrahydrofuran with immobilized columns, revealed a generally decreased ability to successfully resolve the enantiomers of the target analytes, relative to the use of the traditional modifiers, methanol and isopropanol. The stability of the coated columns (Chiralpak AD‐H and Chiralcel OD‐H) was evaluated by injecting “forbidden” solvents, including dichloromethane, dimethyl sulfoxide, and tetrahydrofuran. After 200 injections of these solvents on coated columns, the retention factors and resolutions slightly decreased, and a significant increase in column backpressure was observed, indicating some degree of stationary phase degradation.

  摘要 本研究以一组 30 种外消旋化合物为研究对象，在超临界流体色谱 (SFC) 条件下比较了广泛使用的 "黄金四种 "手性固定相（Chiralpak AD-3、Chiralcel OD-3、Chiralpak AS-3 和 Chiralcel OJ-3）与相应的固定化型手性固定相（Chiralpak IA-3、Chiralpak IB-3、Chiralpak IB N-3、Chiralpak IH-3 和 Chiralpak IJ-3）的性能。使用传统的改性剂甲醇和异丙醇，固定化色谱柱（Chiralpak IB N-3 和 Chiralpak IH-3）在成功分辨目标分析物对映体方面的总体能力优于涂覆型色谱柱（Chiralcel OD-3 和 Chiralpak AS-3）、而涂覆型色谱柱（Chiralpak AD-3、Chiralcel OD-3 和 Chiralcel OJ-3）的性能则优于固定型色谱柱（Chiralpak IA-3、Chiralpak IB-3 和 Chiralpak IJ-3）。对使用固定化色谱柱的非传统修饰剂二氯甲烷、乙酸乙酯和四氢呋喃进行的调查显示，与使用传统修饰剂甲醇和异丙醇相比，成功分辨目标分析物对映体的能力普遍下降。通过注入二氯甲烷、二甲亚砜和四氢呋喃等 "禁用 "溶剂，对涂层柱（Chiralpak AD-H 和 Chiralcel OD-H）的稳定性进行了评估。在涂层色谱柱上注入这些溶剂 200 次后，保留因子和分辨率略有下降，色谱柱背压显著增加，表明固定相发生了一定程度的降解。
• [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
• Direct Catalytic Asymmetric Synthesis of Cyclic Aminals from Aldehydes
  作者：Xu Cheng、Sreekumar Vellalath、Richard Goddard、Benjamin List

  DOI：10.1021/ja8071034

  日期：2008.11.26

  A highly enantioselective Bronsted acid catalyzed direct synthesis of cyclic aminals from aldehydes has been developed. The methodology has been applied to the first asymmetric synthesis of several anti hypertensive aminal drugs including (R)-Thiabutazide.