(E)-4-氯苯乙烯基-4-氯苯基砜 | 6178-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (E)-4-氯苯乙烯基-4-氯苯基砜
• 英文名称: (E)-4-chlorostyryl 4-chlorophenyl sulfone
• 英文别名: (E)-1-(2-((4-chlorophenyl)sulfonyl)vinyl)-4-chlorobenzene；(E)-1-chloro-4-(2-((4-chlorophenyl)sulfonyl)vinyl)benzene；(E)-1-chloro-4-(2-(4-chlorophenylsulfonyl)vinyl)benzene；E-4-chlorostyryl 4-chlorophenyl sulfone；trans-1-(4-Chlor-phenyl)-2-(4-chlor-phenylsulfonyl)-ethylen；1-chloro-4-[(E)-2-(4-chlorophenyl)sulfonylethenyl]benzene
• CAS: 6178-26-3
• 化学式: C₁₄H₁₀Cl₂O₂S
• 分子量: 313.204
• InChiKey: BHZSVOGMDVLRRR-MDZDMXLPSA-N

物化性质

• 熔点：
  163-165 °C
• 沸点：
  492.0±45.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  2

反应信息

• 作为反应物：
  描述：

  trimethylsulfonium iodide 、 (E)-4-氯苯乙烯基-4-氯苯基砜 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以89%的产率得到rac-1-chloro-4-(((1R,2S)-2-(4-chlorophenyl)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)-4-氯苯乙烯基-4-氯苯基砜
  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

• (E)-4-carboxystyrl-4-chlorobenzyl sulfone and pharmaceutical compositions thereof
  申请人：——

  公开号：US20030149109A1

  公开（公告）日：2003-08-07

  Pre-treatment with &agr;,&bgr; unsaturated aryl sulfones protects normal cells from the cytotoxic side effects of two classes of anticancer chemotherapeutics. Administration of a cytoprotective sulfone compound to a patient prior to anticancer chemotherapy with a mitotic phase cell cycle inhibitor or topoisomerase inhibitor reduces or eliminates the cytotoxic side effects of the anticancer agent on normal cells. The cytoprotective effect of the &agr;,&bgr; unsaturated aryl sulfone allows the clinician to safely increasing the dosage of the anticancer chemotherapeutic.

  使用α,β-不饱和芳基磺酮进行预处理可以保护正常细胞免受两类抗癌化疗药物的细胞毒副作用。在患者进行含细胞周期有丝分裂期抑制剂或拓扑异构酶抑制剂的抗癌化疗之前，给予一种细胞保护性磺酮化合物，可以减少或消除抗癌药物对正常细胞的细胞毒副作用。α,β-不饱和芳基磺酮的细胞保护作用使得临床医生可以安全地增加抗癌化疗药物的剂量。
• Styryl sulfone anticancer agents
  申请人：——

  公开号：US20020022666A1

  公开（公告）日：2002-02-21

  Styryl sulfone compounds of the invention selectively inhibit proliferation of tumor cells, and induce apoptosis of tumor cells, while sparing normal cells. The compounds, which are useful in the treatment of cancer and other proliferative disorders, have (a) the formula II: 1 wherein n is zero or one; R 1 is selected from the group consisting of hydrogen, chlorine, fluorine and bromine; R 2 is selected from the group consisting of hydrogen, chlorine, fluorine, bromine, methyl and methoxy; and R 3 is selected from the group consisting of hydrogen, chlorine and fluorine; provided, R 2 may not be methyl or methoxy when R 1 and R 3 are both hydrogen and n is zero or one; and R 1 , R 2 and R 3 may not all be hydrogen when n is one; (b) the formula III: 2 wherein R 1 is selected from the group consisting of hydrogen, chlorine, fluorine and bromine; or (c) or the formula IV: 3 wherein R 1 is selected from the group consisting of fluorine and bromine, and R 2 is selected from the group consisting of 2-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl and 2-nitrophenyl.

  本发明的苯乙烯基磺酰化合物选择性地抑制肿瘤细胞的增殖，并诱导肿瘤细胞凋亡，同时不损害正常细胞。这些化合物在治疗癌症和其他增殖性疾病中很有用，具有以下特征： (a) 公式II： 1 其中 n 是零或一； R 1 选自氢、氯、氟和溴的组； R 2 选自氢、氯、氟、溴、甲基和甲氧基的组；和 R 3 选自氢、氯和氟的组；前提是， 当 R 1 和 R 3 都是氢且 n 是零或一时，R 2 不能是甲基或甲氧基；且 当 n 是一时，R 1 、R 2 和 R 3 不能都是氢； (b) 公式III： 2 其中 R 1 选自氢、氯、氟和溴的组；或 (c) 公式IV： 3 其中 R 1 选自氟和溴的组，R 2 选自2-氯苯基、4-氯苯基、4-氟苯基和2-硝基苯基的组。
• Michael adducts of vinyl sulfones - source for thiadiazoles, oxadiazoles and triazoles
  作者：Venkatapuram Padmavathi、Guda Dinneswara Reddy、Gali Sudhakar Reddy

  DOI：10.1002/jhet.5570450613

  日期：2008.11

  A new and novel five membered heterocycles thiadiazoles, oxadiazoles and triazoles were prepared from methyl 4-arylsulfonyl-3-arylbutyrate and methyl 4-arylmethanesulfonyl-3-arylbutyrate.

  由4-芳基磺酰基-3-芳基丁酸甲酯和4-芳基甲磺酰基-3-芳基丁酸甲酯制备了新颖的五元杂环噻二唑，恶二唑和三唑。
• Mn(<scp>iii</scp>)-mediated regioselective synthesis of (E)-vinyl sulfones from sodium sulfinates and nitro-olefins
  作者：Gang Nie、Xiaocong Deng、Xue Lei、Qinquan Hu、Yunfeng Chen

  DOI：10.1039/c6ra17842a

  日期：——

  An efficient Mn(III)-mediated coupling reaction of sodium sulfinates with nitro-olefins has been developed, this reaction proceeds in mild and open-flask conditions to afford (E)-vinyl sulfones with high regioselectivities and in good to excellent yields. The control experiments revealed that this transformation could involve a radical process.

  已经开发了亚磺酸钠与硝基烯烃的有效的Mn（III）介导的偶联反应，该反应在温和的开瓶条件下进行，以提供具有高区域选择性和良好至优异产率的（E）-乙烯基砜。对照实验表明，这种转化可能涉及一个根本过程。
• 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。