(E)-1-(2-((4-chlorophenyl)sulfonyl)vinyl)-4-fluorobenzene | 56267-73-3

• 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: (E)-1-(2-((4-chlorophenyl)sulfonyl)vinyl)-4-fluorobenzene
• 英文别名: (E)-1-fluoro-4-(2-(4-chlorophenylsulfonyl)vinyl)benzene；(E)-1-chloro-4-((4-fluorostyryl)sulfonyl)benzene；(E)-4-fluorostyryl 4-chlorophenyl sulfone；(E)-4-fluorostyryl-4-chlorophenylsulfone；1-[(E)-2-(4-chlorophenyl)sulfonylethenyl]-4-fluorobenzene
• CAS: 56267-73-3
• 化学式: C₁₄H₁₀ClFO₂S
• 分子量: 296.75
• InChiKey: QZNASRUXPCBZGS-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trimethylsulfonium iodide 、 (E)-1-(2-((4-chlorophenyl)sulfonyl)vinyl)-4-fluorobenzene 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以75%的产率得到rac-1-chloro-4-(((1R,2S)-2-(4-fluorophenyl)cyclopropyl)sulfonyl)benzene
  参考文献：
  名称：

  Naidu, M. S. R.; Bhaskar Reddy, D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 12, p. 1092 - 1094

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl (((4-chlorophenyl)thio)methyl)phosphonate 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 4.0h， 生成 (E)-1-(2-((4-chlorophenyl)sulfonyl)vinyl)-4-fluorobenzene
  参考文献：
  名称：

  Discovery of Vinyl Sulfones as a Novel Class of Neuroprotective Agents toward Parkinson’s Disease Therapy

  摘要：

  Although the etiology of Parkinson's disease (PD) remains elusive, recent studies suggest that oxidative stress contributes to the cascade leading to dopaminergic (DAergic) neurodegeneration. The Nrf2, signaling is the main pathway responsible for cellular defense system against oxidative stress. Nrf2 is a transcription factor that regulates environmental stress response by inducing expression of antioxidant enzyme genes. We have synthesized novel vinyl sulfone derivatives. They exhibited a broad range of activities in inducing HO-1, whose gene expression is under the control of Nrf2. Among them, compound 12g was confirmed to activate Nrf2 and induce expression of the Nrf2-dependent antioxidant enzymes NQO1, GCLC, GLCM, and HO-1, at both mRNA and protein levels in DAergic neuronal cells. This was accompanied by protection of DAergic neurons in both in vitro and MPTP-induced in vivo models of PD. In addition, compound 12g effectively resulted in attenuation of the PD-associated behavioral deficits in the mouse model.

  DOI：

  10.1021/jm401788m

文献信息

• PHASE TRANSFER CATALYZED CYCLOPROPANATION OF TRANS-STYRYL ARYL SULFONES WITH DIMETHYL SULFOXONIUM METHYLIDE
  作者：A. Padmaja、K. Ramachandra Reddy、N. Subba Reddy、D. Bhaskar Reddy

  DOI：10.1080/10426509908031621

  日期：1999.9.1

  Abstract Some new trans-aryl cyclopropyl sulfones (II) have been prepared by the cycloaddition of dimethylsulfoxonium methylide to trans-styryl aryl sulfones (I) by two different methods. It is observed that the reaction in presence of a phase transfer catalyst proceeds in a facile manner.

  摘要 通过二甲基亚砜与反式苯乙烯基芳基砜（I）的环加成反应，通过两种不同的方法制备了一些新的反式芳基环丙基砜（II）。观察到在相转移催化剂存在下的反应以容易的方式进行。
• Synthesis of Vinyl Sulfones via I₂ -mediated Alkene Sulfonylations with Thiosulfonates
  作者：Sang Joon Hwang、Pranab K. Shyam、Hye-Young Jang

  DOI：10.1002/bkcs.11426

  日期：2018.4

  sulfonylation strategy involving I2 and thiosulfonates, as sulfonyl‐group precursors, is reported for the synthesis of vinyl sulfones. Sulfonyl radicals are presumed to be generated from thiosulfonates, which subsequently react with styrene or cinnamic acid derivatives to afford a variety of vinyl sulfones under the described reaction conditions. Detailed conditions, the substrate scope, and mechanistic studies

  据报道，一种简单的磺酰化策略涉及I 2和作为磺酰基基团前体的硫代磺酸盐，用于合成乙烯基砜。推测磺酰基产生了磺酰基，其随后在描述的反应条件下与苯乙烯或肉桂酸衍生物反应以提供各种乙烯基砜。讨论了详细的条件，基材范围和机理研究。
• Decarboxylative sulfonylation of arylpropiolic acids with sulfinic acids: synthesis of (E)-vinyl sulfones
  作者：Jatuporn Meesin、Praewpan Katrun、Vichai Reutrakul、Manat Pohmakotr、Darunee Soorukram、Chutima Kuhakarn

  DOI：10.1016/j.tet.2016.01.042

  日期：2016.3

  Na2CO3 as a promoter and arenesulfinic acids as sulfonylating reagents. This simple and environmentally benign transformation offers an alternative approach and allows for easy and rapid synthesis of (E)-vinyl sulfones from arylpropiolic acids and arenesufinic acids.

  芳基丙酸的脱羧磺酰化已经通过简单地使用Na 2 CO 3作为促进剂和芳烃磺酸作为磺酰化试剂来实现。这种简单且对环境无害的转化提供了一种替代方法，并允许从芳基丙酸和戊烯二酸轻松快速地合成（E）-乙烯基砜。
• A Study of Graphene‐Based Copper Catalysts: Copper(I) Nanoplatelets for Batch and Continuous‐Flow Applications
  作者：Sonia De Angelis、Mario Franco、Alessandra Triminì、Ana González、Raquel Sainz、Leonardo Degennaro、Giuseppe Romanazzi、Claudia Carlucci、Valentina Petrelli、Alejandro de la Esperanza、Asier Goñi、Rafael Ferritto、José Luis Aceña、Renzo Luisi、M. Belén Cid

  DOI：10.1002/asia.201900781

  日期：2019.9.2

  heterogeneous Cu catalysts and systematically evaluated their composition and catalytic activity in azide-alkyne cycloadditions as a model reaction. The use of sustainable graphite nanoplatelets (GNPs) afforded a stable CuI catalyst with good recyclability properties, which are compatible with flow conditions, and able to catalyze other reactions such as the regio- and stereoselective sulfonylation of alkynes (addition

  石墨烯衍生物作为载体的使用改善了非均相催化剂的性能，其中最常用的是氧化石墨烯（GO）。为了探索更绿色的可能性，并深入了解不同石墨烯载体（GO，rGO，炭黑和石墨纳米片）的作用，我们在相同的标准条件下制备了多种异质铜催化剂，并进行了系统评估它们在叠氮化物-炔烃环加成反应中的组成和催化活性作为模型反应。使用可持续的石墨纳米片（GNP）可提供具有良好可回收性的稳定CuI催化剂，该催化剂可与流动条件兼容，
• Synthesis of α,β-Ethylenic Sulfones
  作者：M. Seshapathi、Rao Naidu、D. Bhaskar Reddy

  DOI：10.1246/bcsj.48.1091

  日期：1975.3

  A series of new α,β-ethylenic sulfones were prepared by the condensation of p-chlorophenylsulfonylacetic acid with various aryl aldehydes. The UV and IR spectra of all these compounds were recorded. Their IR spectra exhibited medium to strong bands in the region 1000–975 cm−1, characteristic of trans ethylenic compounds.

  对氯苯基磺酰基乙酸与多种芳基醛缩合制备了一系列新的α，β-乙烯砜。记录了所有这些化合物的紫外和红外光谱。它们的红外光谱在 1000-975 cm-1 区域显示出中等到较强的条带，这是反式乙烯化合物的特征。