2,5-dioxopyrrolidin-1-yl 3,5-bis(trifluoromethyl)benzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-dioxopyrrolidin-1-yl 3,5-bis(trifluoromethyl)benzoate
• 英文别名: 3,5-Bis(trifluoromethyl)benzoic acid succinimidyl ester；(2,5-dioxopyrrolidin-1-yl) 3,5-bis(trifluoromethyl)benzoate
• 化学式: C₁₃H₇F₆NO₄
• 分子量: 355.193
• InChiKey: XFTJSIVLGKAFPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,5-dioxopyrrolidin-1-yl 3,5-bis(trifluoromethyl)benzoate 在 4-二甲氨基吡啶 、 palladium on activated carbon 、 氢气 、 戴斯-马丁氧化剂 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 66.5h， 生成
  参考文献：
  名称：

  10',11'-MODIFIED SAXITOXINS USEFUL FOR THE TREATMENT OF PAIN

  摘要：

  本文提供了化合物、包含这些化合物的药物组合物，以及使用这些化合物和组合物治疗与电压门控钠通道功能相关的疾病的方法，例如与疼痛相关的疾病。这些化合物是10′,11′-修饰的鲍毒素。这些化合物还可以在碳13处进行额外修饰。在某些实施例中，10′,11′-修饰的鲍毒素具有以下式I：其中R1、R2和R3如本文所述。本文还提供了治疗哺乳动物疼痛的方法，包括向哺乳动物投予有效治疗量的10′,11′修饰的鲍毒素或组合物。在一个实施例中，该哺乳动物是人类。

  公开号：

  US20170029431A1
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 3,5-双三氟甲基苄醇 在 碘苯二乙酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以87%的产率得到2,5-dioxopyrrolidin-1-yl 3,5-bis(trifluoromethyl)benzoate
  参考文献：
  名称：

  N-Hydroxysuccinimide-promoted Oxidation of Primary Alcohols and Aldehydes to Form Active Esters with Hypervalent(III) Iodine

  摘要：

  开发了一种简单、温和且高效的方法，利用高产率的(二乙酰氧碘)苯将伯醇和醛转化为N-羟基琥珀酰亚胺酯。N-羟基琥珀酰亚胺在此反应中不仅作为酯化伴侣，还作为PhI(OAc)2的活化剂。

  DOI：

  10.1246/cl.2006.566

文献信息

• Novel Chiral Selector Based on Mefloquine - A Comparative NMR Study to Elucidate Intermolecular Interactions with Acidic Chiral Selectands
  作者：Michal Kohout、Hanspeter Kählig、Denise Wolrab、Alexander Roller、Wolfgang Lindner

  DOI：10.1002/chir.22029

  日期：2012.11

  synthesis, ab initio calculations, and a comparative nuclear magnetic resonance study of a novel chiral mefloquine‐based selector (SO) are presented. On a series of variously N‐acyl protected leucine selectands (SAs), a feasibility study of mefloquine carbamate as a basic chiral solvating agent, and potential fluorophilic high‐performance liquid chromatography selector has been undertaken and evaluated.

  本文介绍了一种新型手性甲氟喹选择剂（SO）的合成，从头算和对核磁共振的比较研究。在一系列由N-酰基保护的亮氨酸选择链（SAs）上，进行了甲氟喹啉作为基本手性溶剂化剂和潜在的高效液相色谱选择剂的可行性研究。在新的SO和叔丁基氨基甲酰基奎尼丁之间作了一个比喻作为参考。手性24：936–943，2012年。分级为4 +©2012 Wiley Periodicals，Inc.
• Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of <i>N-</i>Hydroxysuccinimidyl Formate as CO Surrogate
  作者：Anaïs Barré、Mihaela-Liliana Ţînţaş、Florent Alix、Vincent Gembus、Cyril Papamicaël、Vincent Levacher

  DOI：10.1021/acs.joc.5b01119

  日期：2015.7.2

  An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)(2)/Xantphos catalyst system.
• Scalable Synthesis of <i>N</i>-Acylaziridines from <i>N</i>-Tosylaziridines
  作者：Heather Rubin、Jennifer Cockrell、Jeremy B. Morgan

  DOI：10.1021/jo401267j

  日期：2013.9.6

  N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N-tosylaztridines and reprotection with N-hydroxysuccinimide derivatives is described. Mono- and disubstituted aziridines perform well, with complete retention of stereochemical purity. The consistently moderate yields are linked to the N-tosylaziridine deprotection step, while acylation with N-hydroxysuccinimide derivatives is highly efficient.
• Merging Nucleophilic and Hydrogen Bonding Catalysis: An Anion Binding Approach to the Kinetic Resolution of Propargylic Amines
  作者：Eric G. Klauber、Chandra Kanta De、Tejas K. Shah、Daniel Seidel

  DOI：10.1021/ja105337h

  日期：2010.10.6

  An efficient kinetic resolution of primary propargylic amines with s-factors of up to 56 is reported. The strategy is based on a dual catalytic approach, namely the use of a newly developed and easy-to-make thiourea-amide anion binding catalyst in combination with 4-(dimethylamino)pyridine (DMAP), both employed at a 5 mol% catalyst loading. Benzylic amines are also resolved with s-factors of up to 38.
• LYSINE REACTIVE PROBES AND USES THEREOF
  申请人：The Scripps Research Institute

  公开号：US20210255193A1

  公开（公告）日：2021-08-19

  Disclosed herein are methods and compounds for profiling a lysine reactive protein. Also described herein are methods, compounds, and compositions for identifying a small molecule fragment ligand that interacts with a reactive lysine residue.