4-fluorophenethyl trifluoromethanesulfonate | 1551578-00-7

• 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: 4-fluorophenethyl trifluoromethanesulfonate
• 英文别名: 2-(4-fluorophenyl)ethyl trifluoromethanesulfonate；2-(4-Fluorophenyl)ethyl trifluoromethanesulfonate
• CAS: 1551578-00-7
• 化学式: C₉H₈F₄O₃S
• 分子量: 272.22
• InChiKey: MNWRPTQYEYDBLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-fluorophenethyl trifluoromethanesulfonate 在 二氢吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 36.0h， 生成 phenyl 5-(4-fluorophenyl)pentanoate
  参考文献：
  名称：

  烷基硫蒽盐与活化烯烃的可见光促进脱硫烷基化

  摘要：

  涉及通过光化学从伯醇产生的烷基自由基的反应是罕见且具有挑战性的。在此，我们提出了一种不含光催化剂和金属的方法，该方法能够从相应的醇中产生烷基自由基，并随后通过烷基硫鎓盐与活化烯烃形成C(sp 3 )-C(sp 3 ) 键/ Hantzsch 酯电子供体-受体复合物。该将 C-OH 键转换为 C-C 键的方案具有高度的功能耐受性，可成功用于药物的后期功能化。

  DOI：

  10.1021/acs.orglett.2c01525
• 作为产物：
  描述：

  三氟甲磺酸酐 、 对氟苯乙醇 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-fluorophenethyl trifluoromethanesulfonate
  参考文献：
  名称：

  烷基硫蒽盐与活化烯烃的可见光促进脱硫烷基化

  摘要：

  涉及通过光化学从伯醇产生的烷基自由基的反应是罕见且具有挑战性的。在此，我们提出了一种不含光催化剂和金属的方法，该方法能够从相应的醇中产生烷基自由基，并随后通过烷基硫鎓盐与活化烯烃形成C(sp 3 )-C(sp 3 ) 键/ Hantzsch 酯电子供体-受体复合物。该将 C-OH 键转换为 C-C 键的方案具有高度的功能耐受性，可成功用于药物的后期功能化。

  DOI：

  10.1021/acs.orglett.2c01525

文献信息

• Enabling the Use of Alkyl Thianthrenium Salts in Cross‐Coupling Reactions by Copper Catalysis
  作者：Cheng Chen、Minyan Wang、Hongjian Lu、Binlin Zhao、Zhuangzhi Shi

  DOI：10.1002/anie.202109723

  日期：2021.9.27

  used groups in organic synthesis. Here, a a series of thianthrenium salts have been synthesized that act as reliable alkylation reagents and readily engage in copper-catalyzed Sonogashira reactions to build C(sp3)−C(sp) bonds under mild photochemical conditions. Diverse alkyl thianthrenium salts, including methyl and disubstituted thianthrenium salts, are employed with great functional breadth, since

  烷基是有机合成中应用最广泛的基团之一。在这里，已经合成了一系列的铪盐，它们作为可靠的烷基化试剂，可以很容易地参与铜催化的 Sonogashira 反应，在温和的光化学条件下建立 C(sp 3 )-C(sp) 键。由于敏感的 Cl、Br 和 I 原子在常规方法中耐受性差，因此可以使用多种烷基铪盐，包括甲基和双取代的铪盐，具有很大的功能广度。在铜催化的熊田反应中也证明了所开发的烷基试剂的通用性。
• Synthesis/biological evaluation of hydroxamic acids and their prodrugs as inhibitors for Botulinum neurotoxin A light chain
  作者：Hajime Seki、Sabine Pellett、Peter Šilhár、G. Neil Stowe、Beatriz Blanco、Matthew A. Lardy、Eric A. Johnson、Kim D. Janda

  DOI：10.1016/j.bmc.2013.11.053

  日期：2014.2

  Botulinum neurotoxin A (BoNT/A) is the most potent toxin known. Unfortunately, it is also a potential bioweapon in terrorism, which is without an approved therapeutic treatment once cellular intoxication takes place. Previously, we reported how hydroxamic acid prodrug carbamates increased cellular uptake, which translated to successful inhibition of this neurotoxin. Building upon this research, we

  肉毒杆菌神经毒素 A (BoNT/A) 是已知的最有效的毒素。不幸的是，它也是恐怖主义中的一种潜在生物武器，一旦发生细胞中毒，它就没有获得批准的治疗方法。以前，我们报道了异羟肟酸前药氨基甲酸酯如何增加细胞摄取，从而成功抑制这种神经毒素。在这项研究的基础上，我们详细介绍了 BoNT/A 蛋白酶分子建模研究，并伴随着基于 2,4-二氯肉桂异羟肟酸支架及其氨基甲酸酯前药衍生化的小型异羟肟酸文库的构建，以及对这些分子的酶促和评估细胞模型。
• WO2020050729A5
  申请人：——

  公开号：WO2020050729A5

  公开（公告）日：2022-06-23
• A RADIOLABELLED COMPOUND OF QUATERNARY AMMONIUM SALT OF A POLYCYCLIC AROMATIC AMINE, THE USE OF THE RADIOLABELLED COMPOUND IN A DIAGNOSTIC METHOD OF POSITRON EMISSION TOMOGRAPHY, AND A PHARMACEUTICAL COMPOSITION CONTAINING THE RADIOLABELLED COMPOUND OF QUATERNARY AMMONIUM SALT OF A POLYCYCLIC AROMATIC AMINE
  申请人：Synektik S.A.

  公开号：EP3814325A1

  公开（公告）日：2021-05-05
• RADIOLABELLED COMPOUND OF A QUATERNARY AMMONIUM SALT OF A POLYCYCLIC AROMATIC AMINE AND METHODS OF MANUFACTURING AND DIAGNOSTIC USE THEREOF
  申请人：SYNEKTIK S.A.

  公开号：US20210338847A1

  公开（公告）日：2021-11-04

  The disclosure relates to a radioisotope-labelled compound having a structure according to formula I, wherein a wavy line indicates a single bond between a non-nodal carbon atom of a polycyclic aromatic system and an R 1 substituent selected from a hydrogen; a halogen; a hydroxy; a protected hydroxy; a C 1-4 alkoxy; a nitro group; an amino group; an amino group having 1 hydrogen replaced with a C 1 -C 6 alkyl group; an amino group having 2 hydrogens replaced with a C 1 -C 6 alkyl group; an amino group having 2 hydrogen atoms replaced with C 2-5 alkylene to form a heterocyclic ring; a chain C 1-6 carbon group; a chain C 1-6 carbon group having a substituent selected from a halogen, carboxyl, a formyl, and a C 1-4 alkanesulfonic; a phenyl group; a phenyl group having 1-5 substituents independently selected from halogens, a chain C 1-6 carbon, a halogenated chain C 1-6 carbon substituent, a hydroxy, a protected hydroxy, a C 1-4 alkoxy, and an amino group having 1-2 atoms of hydrogen replaced with C 1-6 alkyl; wherein R 2 is a chain aliphatic substituent having: a total of 1-16 carbon atoms, an atom of 18 F fluorine radioisotope replacing a hydrogen atom at one of the carbon atoms, and a —CH 2 fragment as a terminal member of a chain, wherein the chain connects to one of a hydrogen, a phenyl group, and a phenyl group having 1-3 substituents selected from halogens and C 1-6 alkyl, and wherein if the chain contains at least 2 carbon atoms and there is a bivalent link between the chain carbon atoms, then the bivalent link is selected from the group consisting of an oxygen atom —O—, a sulfur atom —S—, and a C 3-6 cycloalkylene; wherein R 3 and R 4 are combined to form a bivalent butadienyl-1,3 substituent whose terminal carbon atoms are linked to adjacent non-nodal carbon atoms of a B ring to form an aromatic C ring fused with an A and B ring system, having R 1 substituents at non-nodal carbon atoms; wherein n is an integer of 9; wherein X − is a pharmaceutically acceptable counter ion selected from: an anion of a mono-basic inorganic acid, a mononegative anion of a multi-basic inorganic acid, an anion of an alkane carboxylic acid, an anion of an aliphatic sulfonic acid, an anion of an aromatic sulfonic acid, an anion of an acidic amino acid, a hydrate thereof, and a solvate thereof.