trifluoromethane sulfonic anhydride | 75975-45-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trifluoromethane sulfonic anhydride
• 英文别名: trifluoromethanesulfonic anhydride；tert-butyl sulfonic anhydride；tert-butylsulfonic anhydride；triflic anhydride；Tf2O；Tert-butylsulfonyl 2-methylpropane-2-sulfonate
• CAS: 75975-45-0
• 化学式: C₈H₁₈O₅S₂
• 分子量: 258.36
• InChiKey: JUWLWILZEJAZOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  337.4±11.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  94.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trifluoromethane sulfonic anhydride 、 5-hydroxy-7-methoxy-2,2-dimethyl-benzo[1,3]dioxin-4-one 在 吡啶 作用下， 以95%的产率得到三氟甲烷磺酸7-甲氧基-2,2-二甲基-4-氧代-4H-1,3-苯并二氧杂环己-5-基酯
  参考文献：
  名称：

  Stereoselective total synthesis of paecilomycin E

  摘要：

  First total synthesis of recently isolated resorcylic acid lactone paecilomycin E has been accomplished. The key reactions include olefin metathesis, Mitsunobu reaction, Stille coupling and regioselective allylation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.137
• 作为产物：
  描述：

  二-叔-丁基三硫化物 在 二甲基二环氧乙烷 作用下， 以 氘代氯仿 为溶剂， 反应 726.0h， 生成 trifluoromethane sulfonic anhydride
  参考文献：
  名称：

  Synthesis and Decomposition of Tri- and Tetraoxide Derivatives of Dialkyl Trisulfides

  摘要：

  The first isolation and characterization of sulfinyl sulfonyl thioanhydride 1 and its tetrasulfide analog are presented here, along with those of disulfonyl thio- and dithioanhydrides 2. The oxidation of various substrates at different temperatures has shown that, contrary to current belief, oxidation takes place regiospecifically at the external sulfinyl sulfur rather than at the internal sulfenyl sulfur. The decomposition of these compounds has also been investigated and was found to be consistent with the mechanism proposed for the decomposition of trisulfide monoxides.

  DOI：

  10.1021/jo952244l
• 作为试剂：
  描述：

  O-tert-butyldiphenylsilyl benzhydroxamate 在 trifluoromethane sulfonic anhydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.3h， 生成 苯甲腈 N-氧化物
  参考文献：
  名称：

  O-甲硅烷基化异羟肟酸生成的炔烃和氧化腈之间的 1,3-偶极环加成反应合成 3,5-二取代异恶唑

  摘要：

  在本文中，我们报告了在三氟甲磺酸酐和 NEt3 存在下，由 O-硅烷化异羟肟酸原位生成的炔基偶极亲和物和腈氧化物偶极之间的 1,3-偶极环加成反应，区域选择性合成 3,5-二取代异恶唑。由于该策略提供了温和、无金属和无氧化剂的条件，该反应成功地应用于各种炔基偶极亲和体，证明了这种方法对不同官能团的耐受性。特别是，我们已经证明该方法与生物分子如肽和肽核酸 (PNA) 兼容。该方案构成了导致异恶唑区域选择性形成的无金属 1,3-偶极环加成的另一个例子。

  DOI：

  10.1002/ejoc.201901045

文献信息

• Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions of Enantiomerically Enriched Potassium β-Trifluoroboratoamides with Various Aryl- and Hetaryl Chlorides
  作者：Gary A. Molander、Inji Shin、Ludivine Jean-Gérard

  DOI：10.1021/ol101865e

  日期：2010.10.1

  Enantiomerically enriched potassium β-trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki−Miyaura cross-coupling reactions were carried out with various aryl- and hetaryl chlorides in good to excellent yields. Moreover, the diastereoselectivities were preserved throughout the Suzuki−Miyaura

  使用伪麻黄碱作为手性助剂，以大于 95:5 的比例合成了富含对映异构体的 β-三氟硼酰胺钾作为空气稳定的固体。使用这些手性亲核试剂，铃木-宫浦交叉偶联反应与各种芳基氯化物和杂芳基氯化物进行了良好到极好的产率。此外，在整个 Suzuki-Miyaura 交叉偶联反应中都保留了非对映选择性。
• The Organocatalytic Asymmetric Prins Cyclization
  作者：Gavin Chit Tsui、Luping Liu、Benjamin List

  DOI：10.1002/anie.201500219

  日期：2015.6.22

  We describe here the design and development of an organocatalytic Prins cyclization. In the presence of a confined chiral imidodiphosphoric acid catalyst, salicylaldehydes react with 3‐methyl‐3‐buten‐1‐ol to afford highly functionalized 4‐methylenetetrahydropyrans in excellent regio‐ and enantioselectivity. The extreme steric demand of the acid catalyst is key for the success of this transformation

  我们在这里描述有机催化Prins环化的设计和开发。在受限的手性亚胺基二磷酸催化剂存在下，水杨醛与3-甲基-3-丁烯-1-醇反应，以高度的区域选择性和对映体选择性提供高度官能化的4-亚甲基四氢吡喃。酸催化剂的极端空间需求是该转化成功的关键。
• Tailored Functionalization of Polyphenol-Based Molecular Platforms
  作者：Roy Lavendomme、Axel Leroy、Michel Luhmer、Ivan Jabin

  DOI：10.1021/jo501021c

  日期：2014.7.18

  methodology for the iteroselective functionalization of polyphenolic platforms by N-tert-butylaminocarbonyl (Bac) groups. The methodology consists of reacting the oligomeric platform with t-BuNCO and an inorganic base in an apolar solvent. This very simple one-step procedure has been applied to various calix[4, 5, 6, and 8]arenes, and in all cases, calixarenes with a single leftover phenolic moiety

  选择性修饰大环低聚物的通用且有效的方法很少见，主要是因为难以将反应限制在一定数量的相同官能团上。这项工作描述了由多酚平台iteroselective官能一个独特的，一般情况下，合理的方法ñ -叔-butylaminocarbonyl（BAC）组。该方法包括使低聚平台与t反应-BuNCO和非极性溶剂中的无机碱。此非常简单的一步步骤已应用于各种杯[4、5、6和8]芳烃，并且在所有情况下，均以高收率（> 90％）分离了具有单个剩余酚部分的杯芳烃。有趣的是，这种所谓的“一劳永逸”的方法可以直接访问具有固有手性的杯芳烃。还显示了BAC基团可以用作保护基团。因此，仅用一种方法已用于关键前体平台的有效单功能化，说明了其用于复杂大环低聚物定制合成的巨大潜力。
• METHOD FOR PRODUCING CYCLIC SULFONIC ACID ESTER AND INTERMEDIATE THEREOF
  申请人：Kuramoto Ayako

  公开号：US20120130089A1

  公开（公告）日：2012-05-24

  The present invention is directed to provide an efficient production method which is capable of not only obtaining a cyclic sulfonic acid ester (sultone) at low cost and in high yield, but also the sulfonic acid ester (sultone) stably even in a commercial scale. The present invention relates to a method for producing hydroxysultone comprising a first step where a diol having a specified structure and a thionyl halide are reacted to obtain a cyclic sulfite having a specified structure, and a second step where the cyclic sulfite is reacted with water or/and alcohol; a method for producing an unsaturated sultone having a specified structure comprising a third step where a hydroxylsultone having a specified structure is reacted with an acid halide or an acid anhydride to obtain an intermediate, subsequently the intermediate is treated with a base; as well as a cyclic sulfite having a specified structure.

  本发明旨在提供一种高效的生产方法，该方法不仅能够以低成本和高产率获得环状磺酸酯（磺酮），而且能够在商业规模下稳定地生产磺酸酯（磺酮）。本发明涉及一种生产羟基磺酮的方法，包括第一步，其中将具有特定结构的二元醇和硫酰卤反应，以获得具有特定结构的环状亚磺酸酯，以及第二步，其中将环状亚磺酸酯与水或/和醇反应；一种生产具有特定结构的不饱和磺酮的方法，包括第三步，其中将具有特定结构的羟基磺酮与酸卤或酸酐反应，以获得中间体，随后用碱处理中间体；以及具有特定结构的环状亚磺酸酯。
• 1,3-propanesultone derivative useful in the preparation of a 1,3-propenesultone derivative
  申请人：Wako Pure Chemical Industries, Ltd.

  公开号：EP2757102A1

  公开（公告）日：2014-07-23

  The present invention is directed to provide an efficient production method which is capable of not only obtaining a cyclic sulfonic acid ester (sultone) at low cost and in high yield, but also the sulfonic acid ester (sultone) stably even in a commercial scale. The present invention relates to a method for producing hydroxysultone comprising a first step where a diol having a specified structure and a thionyl halide are reacted to obtain a cyclic sulfite having a specified structure, and a second step where the cyclic sulfite is reacted with water or/and alcohol; a method for producing an unsaturated sultone having a specified structure comprising a third step where a hydroxylsultone having a specified structure is reacted with an acid halide or an acid anhydride to obtain an intermediate, subsequently the intermediate is treated with a base; as well as a cyclic sulfite having a specified structure.

  本发明旨在提供一种高效的生产方法，该方法不仅能够低成本、高产率地获得环状磺酸酯（磺内酯），而且即使在商业规模上也能稳定地获得磺酸酯（磺内酯）。本发明涉及一种生产羟基磺酸内酯的方法，包括第一步：具有特定结构的二元醇与亚 硫酰卤反应，得到具有特定结构的环状亚硫酸盐；第二步：环状亚硫酸盐与水或/和醇反应；一种生产具有特定结构的不饱和舒尔酮的方法，包括第三步：具有特定结构的羟基舒尔酮与酸卤化物或酸酐反应，得到中间体，然后用碱处理中间体；以及具有特定结构的环状亚硫酸盐。