benzimidazolium triflate | 99257-95-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: benzimidazolium triflate
• 英文别名: 1H-benzimidazol-3-ium;trifluoromethanesulfonate
• CAS: 99257-95-1
• 化学式: CHF₃O₃S*C₇H₆N₂
• 分子量: 268.216
• InChiKey: IWYHWZTYVNIDAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  91.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-O-(p,p'-dimethoxytrityl)thymidine 3'-(allyl N,N-diisopropylphosphoramidite) 、 benzimidazolium triflate 以 氘代乙腈 为溶剂， 反应 0.02h， 生成 diisopropylammonium trifluoromethanesulfonate 、 1-[(2R,4S,5R)-4-[benzimidazol-1-yl(prop-2-enoxy)phosphanyl]oxy-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Benzimidazolium Triflate as an Efficient Promoter for Nucleotide Synthesis via the Phosphoramidite Method

  摘要：

  DOI：

  10.1021/jo961569e
• 作为产物：
  描述：

  苯并咪唑 、 三氟甲磺酸 以 二氯甲烷 为溶剂， 生成 benzimidazolium triflate
  参考文献：
  名称：

  双碳硼烷桥连双糖膦酸盐作为 BNCT 的富硼传递剂

  摘要：

  报道了含有 glycophosphonate 和 glycophosphonothioate 部分的富含硼的双（间碳硼烷）衍生物的合成和性质。所有化合物都是水溶性的；然而，四半乳糖基化化合物的溶解度低于其二钠盐。

  DOI：

  10.1002/ejoc.201000213
• 作为试剂：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite] 、 alkaline earth salt of/the/ methylsulfuric acid 在 邻苯二甲酸二甲酯 、 3 A molecular sieve 、 ethylmethyldioxirane 、 benzimidazolium triflate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.1h， 生成 2-cyanoethyl [5'-O-(p,p'-dimethoxytrityl)-2'-deoxycytosylyl]-(3',5')-3'-O-(tert-butyldimethylsilyl)thymidine
  参考文献：
  名称：

  Ethyl(methyl)dioxirane as an Efficient Reagent for the Oxidation of Nucleoside Phosphites into Phosphates under Nonbasic Anhydrous Conditions

  摘要：

  [GRAPHICS]A convenient method for the oxidation of nucleoside phosphites into phosphates under nonbasic and nonaqueous conditions using commercially available ethyl(methyl)dioxirane has been developed. This oxidation is effective with both N-protected and N-unprotected strategies.

  DOI：

  10.1021/ol000364w

文献信息

• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR SYNTHESIS<br/>[FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS DE SYNTHÈSE
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2018237194A1

  公开（公告）日：2018-12-27

  The present disclosure, among other things, provides technologies for synthesis, including reagents and methods for stereoselective synthesis. In some embodiments, the present disclosure provides compounds useful as chiral auxiliaries. In some embodiments, the present disclosure provides reagents and methods for oligonucleotide synthesis. In some embodiments, the present disclosure provides reagents and methods for chirally controlled preparation of oligonucleotides. In some embodiments, technologies of the present disclosure are particularly useful for constructing challenging internucleotidic linkages, providing high yields and stereoselectivity.

  本公开内容提供了合成技术，包括用于立体选择性合成的试剂和方法。在某些实施例中，本公开内容提供了作为手性辅助剂有用的化合物。在某些实施例中，本公开内容提供了用于寡核苷酸合成的试剂和方法。在某些实施例中，本公开内容提供了用于手性控制寡核苷酸制备的试剂和方法。在某些实施例中，本公开内容的技术特别适用于构建具有挑战性的核苷酸间连接，提供高产率和立体选择性。
• [EN] PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS<br/>[FR] PROCEDE DE PREPARATION DE COMPOSES ENRICHIS EN ENANTIOMERES
  申请人：DSM IP ASSETS BV

  公开号：WO2003099745A1

  公开（公告）日：2003-12-04

  Process for the preparation of enantiomerically enriched compounds with Formula Ar-C(R1)-C(R2)-Z wherein Ar represents an optionally substituted (hetero)aryl group, R1 and R2, each independently, represent H, an alkyl, (hetero)aryl, dialkylamino, amido, thioether, alkoxy or aryloxy group with the proviso that not both R1 and R2 represent H, or R1 and R2 form together with the C-atoms to which they are bound a (hetero)alkyl or (hetero) alkenyl ring and Z represents an electron withdrawing group, in which process a boronic acid derivate of Formula Ar-B(OR3)OR4 or its anhydride, wherein Ar is as described above and R3 and R4, each independently, represent H or an alkyl group, is reacted with an olefinic unsaturated compound with Formula R2 - C = C - (R1)Z, wherein R1, R2 and Z are as described above, in the presence of a transition metal catalyst comprising a transition metal chosen from Cu and group VIII of the Periodic Table and an enantiomerically enriched ligand L, having the Formula (I) where Cn together with the two O-atoms and the P-atom forms a substituted or non-substituted ring with 2-6 C-atoms, R5 and R6 each independently stand for H, an optionally substituted alkyl, aryl, alkaryl, or aralkyl group, or represent the group with Formula (II) wherein Cn1 may have the same meanings as given for Cn and B represents a bridging group, or R5 and R6 may form a heterocyclic ring together with the N-atom to which they are bound.

  制备具有Ar-C(R1)-C(R2)-Z式的对映富集化合物的过程，其中Ar代表可选择取代的(杂)芳基团，R1和R2分别独立地代表H、烷基、(杂)芳基、二烷基氨基、酰胺、硫醚、烷氧基或芳氧基团，但R1和R2不同时代表H，或者R1和R2与它们结合的C原子一起形成(杂)烷基或(杂)烯基环，Z代表一个电子吸引基团，在该过程中，以Formula Ar-B(OR3)OR4或其酐的硼酸衍生物为反应物，其中Ar如上所述，R3和R4分别独立地代表H或烷基团，与Formula R2 - C = C - (R1)Z的烯烃不饱和化合物反应，其中R1、R2和Z如上所述，在Cu和周期表第VIII族的过渡金属选择的过渡金属催化剂存在下，以对映富集的配体L为特征，其具有Formula (I)，其中Cn与两个氧原子和磷原子一起形成具有2-6个C原子的取代或非取代环，R5和R6分别独立地代表H、可选择取代的烷基、芳基、烷芳基或芳基基团，或代表具有Formula (II)的基团，其中Cn1可能具有与Cn相同的含义，B代表一个桥联基团，或者R5和R6可以与它们结合的N原子一起形成一个杂环。
• Process for the preparation of enantiomerically enriched compounds
  申请人：DSM IP Assets B.V.

  公开号：EP1364932A1

  公开（公告）日：2003-11-26

  Process for the preparation of enantiomerically enriched compounds with formula Ar - C(R1) - C(R2) - Z wherein Ar represents an optionally substituted (hetero)aryl group, R1 and R2, each independen tly, represent H, an alkyl, (hetero)aryl, dialkylamino, amido, thioether, alkoxy or aryloxy group with the proviso that not both R1 and R2 represent H, or R1 and R2 form together with the C-atoms to which they are bound a (hetero)alkyl or (hetero) alkenyl ring and Z represents an electron withdrawing group, in which process a boronic acid derivate of formula Ar - B(OR3)OR4 or its anhydride, wherein Ar is as described above and R3 and R4, each independently, represent H or an alkyl group, is reacted with an olefinic unsaturated compound with formula R2 - C = C - (R1)Z, wherein R1, R2 and Z are as described above, in the presence of a transition metal catalyst comprising a transition metal chosen from Cu and group VIII of the Periodic Table and an enantiomerically enriched ligand L, having the formula (I) where Cn together with the two O-atoms and the P-atom forms a substituted or non-substituted ring with 2-6 C-atoms, R5 and R6 each independently stand for H, an optionally substituted alkyl, aryl, alkaryl or aralkyl group, or represent the group with formula (II) wherein Cn1 may have the same meanings as given for Cn and B represents a bridging group, or R5 and R6 may form a heterocyclic ring together with the N-atom to which they are bound.

  制备具有Ar - C(R1) - C(R2) - Z式的对映体富集化合物的过程，其中Ar代表可选择取代的(杂)芳基团，R1和R2分别独立地代表H、烷基、(杂)芳基、二烷基氨基、酰胺、硫醚、烷氧基或芳基氧基团，但R1和R2不同时代表H，或者R1和R2与它们结合的C原子一起形成(杂)烷基或(杂)烯基环，Z代表一个电子吸引基团，在该过程中，Ar - B(OR3)OR4式的硼酸衍生物或其酐，其中Ar如上所述，R3和R4分别独立地代表H或烷基团，与具有R2 - C = C - (R1)Z式的烯烃不饱和化合物反应，其中R1、R2和Z如上所述，在Cu和周期表第VIII族中选择的过渡金属和具有式(I)的对映体富集配体L的存在下进行，其中Cn与两个氧原子和磷原子一起形成具有2-6个C原子的取代或非取代环，R5和R6分别独立地代表H、可选择取代的烷基、芳基、烷基芳基或芳基烷基团，或代表具有式(II)的团，其中Cn1可能具有与Cn给定的相同含义，B代表一个桥联基团，或者R5和R6可以与它们结合的N原子一起形成一个杂环。
• Ion transport in a class of imidazole-based liquid/solid protic ionics
  作者：Vincenzo Tricoli、Gabriele Orsini、Martina Anselmi

  DOI：10.1039/c2cp41027c

  日期：——

  A class of protic ionic-compounds were prepared by Brønsted acid–base reaction of imidazole or benzimidazole with one of the following acids: trifluoromethanesulfonic, nonafluorobutanesulfonic, para-toluenesulfonic and trifluoroacetic. Except those based on trifluoroacetic acid, all prepared compounds are thermally stable up to at least 270 °C. They are solid up to temperatures between 134 and 220 °C, depending on their constituent acid and base. A simple physico-mathematical model of ion motion in the lattice was developed and implemented to correctly interpret frequency-dependent electrical response of these materials, particularly in the solid state, and investigate their ion-conducting behavior as a function of temperature. These ionic compounds display sensible ionic conductivity up to ca. 5 × 10−4 and 5 × 10−2 S cm−1 in the solid and molten state, respectively, under fully anhydrous conditions. The presence of absorbed water, after brief exposure to an ambient atmosphere, enhances conduction properties remarkably. Conductivity values up to 10−3 and 10−1 S cm−1 were registered, respectively, in the solid and molten state, after short exposure to (humid) ambient air. It is argued how absorbed water molecules may remove protons from (ImH)+ or (BImH)+ groups, thereby enabling a chain mechanism of proton-hopping through non-protonated Im or BIm sites. It is discussed how these results and methods may inspire designing protic ionic-materials at the solid-state, with enhanced proton conduction even under fully-anhydrous conditions.

  通过咪唑或苯并咪唑与以下酸之一：三氟甲磺酸、九氟丁磺酸、对甲苯磺酸和三氟乙酸的布朗斯台德酸碱反应，制备了一系列质子型离子化合物。除基于三氟乙酸的化合物外，所有制备的化合物在至少270°C温度下均具有热稳定性。它们的固态温度范围为134至220°C，具体取决于所组成的酸和碱。开发并实施了一个简单的物理数学模型来解释这些材料在固态下频率依赖的电响应，并研究它们的离子导电行为随温度的变化。这些离子化合物在完全无水的条件下，分别在固态和熔融状态下显示出高达约5×10⁻⁴和5×10⁻² S/cm的合理离子电导率。短暂暴露于环境气氛后，吸附的水显著增强了传导性能。在短暂暴露于（湿润的）环境空气中后，分别在固态和熔融状态下记录到了高达10⁻³和10⁻¹ S/cm的电导率值。据推测，吸附的水分子可能从（ImH）⁺或（BImH）⁺基团中去除质子，从而通过非质子化的Im或BIm位点实现质子跳跃的链式机制。讨论了这些结果和方法如何启发在固态下设计具有增强质子传导性的质子型离子材料，即使在完全无水的条件下。
• SOLID-PHASE SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING N6-(2-DEOXY-ALPHA,BETA-DERYTHROPENTOFURANOSYL)-2,6-DIAMINO-4-HYDROXY-5-FORMAMIDOPYRIMIDINE (Fapy.dG)
  申请人：The Johns Hopkins University

  公开号：US20210238213A1

  公开（公告）日：2021-08-05

  A strategy using reverse phosphoramidites for synthesizing oligonucleotides containing Fapy.dG is disclosed.

  揭示了一种使用反向磷酰胺酸酯合成含有Fapy.dG的寡核苷酸的策略。