1-(4-氯苯基)-2-[(4-氯苯基)磺酰基]-1-乙酮 | 33046-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-氯苯基)-2-[(4-氯苯基)磺酰基]-1-乙酮
• 英文名称: 1-(4-chlorophenyl)-2-((4-chlorophenyl)thio)ethanone
• 英文别名: 1-(4-chloro-phenyl)-2-(4-chloro-phenylsulfanyl)-ethanone；1-(4-Chlor-phenyl)-2-(4-chlor-phenylmercapto)-aethanon；p-Chlorphenacyl(p-chlorphenyl)sulfid；p-Chlorphenyl-p-chlorphenacylsulfid；1-(4-Chlorophenyl)-2-[(4-chlorophenyl)sulfanyl]-1-ethanone；1-(4-chlorophenyl)-2-(4-chlorophenyl)sulfanylethanone
• CAS: 33046-50-3
• 化学式: C₁₄H₁₀Cl₂OS
• mdl: MFCD00098687
• 分子量: 297.205
• InChiKey: HZGLGBYRTBNBHB-UHFFFAOYSA-N

物化性质

• 熔点：
  112-115°

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)-2-[(4-氯苯基)磺酰基]-1-乙酮 在 盐酸 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 3-(4-chlorophenylsulfonyl)-2-(4-chlorophenyl)-1H-indole
  参考文献：
  名称：

  Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity

  摘要：

  A novel reaction of indole with aryldiazonium salts leading to the formation of 2-aryl-3-(arylazo)indoles was discovered. The products were found to possess potent anti-MRSA and anti-LLVRE activities. The SAR studies indicate that the potentially metabolically labile azo functionality can be replaced with ether oxygen and thioether sulfur atoms without any loss of activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.081
• 作为产物：
  描述：

  4-氯苯乙炔 在 叠氮基三甲基硅烷 、 水 、 四丁基碘化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 1-(4-氯苯基)-2-[(4-氯苯基)磺酰基]-1-乙酮
  参考文献：
  名称：

  在温和条件下通过自由基法电催化合成钆-双芳硫烯胺和α-苯硫酮

  摘要：

  在室温下，在碘化四丁基铵 (TBAI) 作为氧化还原催化剂和电解质的存在下，通过 α-取代的乙烯基叠氮化物与硫醇的偶联，开发了合成偕-双芳硫基烯胺和 α-苯硫酮的新方法。电子特性在生成的产品中至关重要。该协议具有不含金属和氧化剂的材料、对基材的广泛耐受性和温和的反应条件。

  DOI：

  10.1055/a-1335-7902

文献信息

• Pyrazole derivatives from azines of substituted phenacyl aryl/cyclohexyl sulfides and their antimycobacterial activity
  作者：Ramaiyan Manikannan、Ramaiyan Venkatesan、Shanmugam Muthusubramanian、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2010.09.137

  日期：2010.12

  Azines derived from substituted phenacyl aryl/cyclohexyl sulfide on treatment with excess phosphorous oxychloride in N,N-dimethylformamide have been found to yield two isomeric pyrazoles in each case. A plausible mechanism has been suggested for the formation of the products. The antimycobacterial activity of the isomeric compounds has been tested against Mycobacterium tuberculosis (MTB).

  已经发现在N，N-二甲基甲酰胺中用过量的三氯氧化磷处理衍生自取代的苯甲酰基芳基/环己基硫化物的叠氮在每种情况下会产生两种异构的吡唑。已经提出了一种合理的机制来形成产物。已测试了同分异构化合物的抗分枝杆菌活性，可抵抗结核分枝杆菌（MTB）。
• Selective one-pot multicomponent synthesis and anti-tubercular evaluation of 5-(aryl/cyclohexylsulfanyl)-2-alkoxy-4,6-diarylnicotinonitriles
  作者：Ramaiyan Manikannan、Shanmugam Muthusubramanian、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2010.04.025

  日期：2010.6

  A new set of highly substituted pyridine derivatives has been synthesized by a product selective four component reaction of aryl aldehyde, malononitrile and 2-aryl/cyclohexylsulfanyl-1-aryl-1-ethanones in presence of sodium hydroxide in methyl/ethyl alcohol. Among the compounds, 4,6-bis(4-chlorophenyl)-5-[(4-chlorophenyl)sulfanyl]-2-methoxynicotinonitrile (4n) inhibited Mycobacterium tuberculosis (MTB)

  通过在甲醇/乙醇中存在氢氧化钠的情况下，通过芳基醛，丙二腈和2-芳基/环己基硫烷基-1-芳基-乙酮的产物选择性四组分反应合成了一组新的高度取代的吡啶衍生物。在这些化合物中，4,6-双（4-氯苯基）-5-[（4-氯苯基）硫烷基] -2-甲氧基烟腈（4n）抑制结核分枝杆菌（MTB）的最小抑制浓度（MIC）为3.1μM，为比乙胺丁醇和吡嗪酰胺更有效。
• Structure–activity relationship of antileishmanials neolignan analogues
  作者：Mário Aveniente、Eduardo F. Pinto、Lourivaldo S. Santos、Bartira Rossi-Bergmann、Lauro E.S. Barata

  DOI：10.1016/j.bmc.2007.08.016

  日期：2007.12

  Twenty-two synthetic analogues of neolignans comprising beta-ketoethers and beta-ketosulfides were obtained from condensation reactions among beta-bromoketones and phenols or thiophenols, respectively, in basic solutions, and assayed in vitro for activity against intracellular Leishmania amazonensis and Leishmania donovani amastigotes, the causative agents of cutaneous and visceral leishmaniasis. The highest selective activity was found for compounds with sulfur bridges, whereas beta-ketosulphoxides and beta-ketosulphones had significantly less growth inhibitory activity. Compounds 2-[(4-chlorophenyl)thio]propan-1-one and 1-(3,4-dimethoxy)2-[(4-methylphenyl)thio]propan-1-one were the most potent, inhibiting the growth parasite species by over 90% at microgram/mL, but only compound 1-(3,4-dimethoxy)-2-[(4-methylphenyl)thio]propan-1-one was selectively toxic to the parasites. (C) 2007 Elsevier Ltd. All rights reserved.
• Antiproliferative activity of 2,3-disubstituted indoles toward apoptosis-resistant cancers cells
  作者：Igor V. Magedov、Florence Lefranc、Liliya V. Frolova、Laetitia Moreno Y. Banuls、Amanda S. Peretti、Snezna Rogelj、Véronique Mathieu、Robert Kiss、Alexander Kornienko

  DOI：10.1016/j.bmcl.2013.03.110

  日期：2013.6

  Many types of cancer, including glioma, melanoma, NSCLC, among others, are resistant to apoptosis induction and poorly responsive to current therapies with propaptotic agents. We describe a series of 2,3-disubstituted indoles, which display cytostatic rather than cytotoxic effects in cancer cells, and serve as a new chemical scaffold to develop anticancer agents capable of combating apoptosis-resistant cancers associated with dismal prognoses. (C) 2013 Elsevier Ltd. All rights reserved.
• Menon,N.K.; Nargund,K.S., Indian Journal of Chemistry, 1967, vol. 5, p. 478 - 479
  作者：Menon,N.K.、Nargund,K.S.

  DOI：——

  日期：——