4-氯-N-(4-氯苯基)苯磺酰胺 | 599-87-1

• 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: 4-氯-N-(4-氯苯基)苯磺酰胺
• 英文名称: 4-chloro-N-(4-chlorophenyl)benzenesulfonamide
• 英文别名: N-(p-Chlorophenyl)-p-chlorobenzenesulfonamide；4-chloro-benzenesulfonic acid-(4-chloro-anilide)；4-Chlor-benzolsulfonsaeure-(4-chlor-anilid)；4,4'-dichlorobenzenesulfonanilide；4-Chlor-benzolsulfonsaeure-<4-chlor-anilid>；4-Chlor-benzolsulfon-N-(4-chlor-phenyl)-amid
• CAS: 599-87-1
• 化学式: C₁₂H₉Cl₂NO₂S
• 分子量: 302.181
• InChiKey: CALNUDRLRJURKB-UHFFFAOYSA-N

物化性质

• 熔点：
  145.4-146 °C
• 沸点：
  430.3±55.0 °C(Predicted)
• 密度：
  1.492±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 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：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯-N-(4-氯苯基)苯磺酰胺 在 硝酸 作用下， 以96%的产率得到4-chloro-N-(4-chloro-2-nitrophenyl)benzenesulfonamide
  参考文献：
  名称：

  SULFONAMIDE DERIVATIVES

  摘要：

  公开号：

  EP1174028B1
• 作为产物：
  描述：

  4-氯苯磺酰胺 在 sodium hypochlorite 、 乙醇 、 potassium tert-butylate 、 copper diacetate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 56.0h， 生成 4-氯-N-(4-氯苯基)苯磺酰胺
  参考文献：
  名称：

  铜催化氯胺-T与芳基硼酸在室温下反应合成N-芳基磺酰胺

  摘要：

  已经开发了一种铜催化的（杂）芳基硼酸和氯胺-T（或相关化合物）的 Chan-Lam 偶联反应，用于在室温下以中等至良好的收率合成 N-芳基磺酰胺，并具有良好的官能团的耐受性。在此过程中，据信氯胺-T 用作亲电子试剂。

  DOI：

  10.1055/s-0036-1590978

文献信息

• A highly efficient heterogeneous copper-catalyzed Chan–Lam coupling reaction of sulfonyl azides with arylboronic acids leading to N-arylsulfonamides
  作者：Chongren You、Fang Yao、Tao Yan、Mingzhong Cai

  DOI：10.1039/c6ra04298h

  日期：——

  A heterogeneous Chan–Lam coupling reaction between sulfonyl azides and arylboronic acids was achieved in MeOH at room temperature in the presence of 10 mol% of an L-proline-functionalized MCM-41-immobilized copper(I) complex [MCM-41–L-proline–CuCl] under air, yielding a variety of N-arylsulfonamides in excellent yields. The new heterogeneous copper complex can be prepared from commercially readily

  在室温下，在存在10 mol％的L-脯氨酸官能化的MCM-41固定化铜（I）络合物[MCM-41– L]的情况下，在MeOH中实现了磺酰叠氮化物与芳基硼酸之间的异质Chan-Lam偶联反应-脯氨酸–CuCl ]在空气中产生多种N-芳基磺酰胺，收率极高。新的多相铜络合物可以由市售的廉价试剂制备，并通过简单过滤反应溶液进行回收，并循环至少8次而不会降低活性。
• Effect of para Substitution on Dissociation of N-Phenylbenzenesulfonamides
  作者：Martin Mansfeld、Patrik Pařík、Miroslav Ludwig

  DOI：10.1135/cccc20041479

  日期：——

  The reaction of substituted anilines and benzenesulfonyl chlorides has been used to prepare 49 substituted N-phenylbenzenesulfonamides of general formula 4-X-C₆H₄SO₂NHC₆H₄-Y-4'. Their purity was checked by elemental analysis. The substituents X and Y include H, CH₃, CH₃O, Cl, Br, CN, and NO₂. The dissociation constants of all compounds were determined by potentiometric titration in methanol, acetonitrile, N,N-dimethylformamide, and pyridine. The obtained dissociation constants, pK_HA, were correlated with various sets of substituent constants. It was found that the effects of substituents X and Y on the dissociation are best described by using the Hammett equation with σ_p constants and the Yukawa-Tsuno equation with σ_p^- and σ_p constants, respectively. This result confirms the direct conjugation of Y substituent with the reaction centre. The explained variability using the additive model was above 96% in all the solvents used. The data also provided information about the transmission effect of the SO₂ group. The average dissociation constants were further processed by the latent variables methods, principal components and conjugated deviations analyses.

  替代苯胺和苯磺酰氯的反应已被用于制备49种通式为4-X-C₆H₄SO₂NHC₆H₄-Y-4'的取代N-苯基苯磺酰胺。它们的纯度通过元素分析进行了检查。取代基X和Y包括H、CH₃、CH₃O、Cl、Br、CN和NO₂。所有化合物的解离常数通过在甲醇、乙腈、N,N-二甲基甲酰胺和吡啶中的电位滴定确定。获得的解离常数pKHA与各种取代基常数相关联。发现取代基X和Y对解离的影响最好通过使用带有σp常数的Hammett方程和带有σp-和σp常数的Yukawa-Tsuno方程来描述。这一结果证实了Y取代基与反应中心的直接共轭。在所有使用的溶剂中，使用加性模型解释的可变性超过96%。数据还提供了关于SO₂基团的传输效应的信息。平均解离常数进一步通过潜在变量方法、主成分和共轭偏差分析进行处理。
• Variation of transition state in reactions of benzensulfonyl chlorides with anilines in MeOH-MeCN solvents
  作者：Ikchoon Lee、In Sun Koo

  DOI：10.1016/s0040-4020(01)88691-9

  日期：1983.1

  Kinetic studies of nucleophilic substitution reactions of substituted benzensulfonyl chlorides with anilines were conducted at 35° in a range of methanol-acetonitrile solvent mixtures. Results showed that (i) the magnitudes of ϱN and β with a change of suhstituent in the nucleophile are large and indicate a relatively advanced bond-formation in the transition state, (ii) maximum size of ϱN and ϱs β

  取代的苯磺酰氯与苯胺的亲核取代反应的动力学研究是在35°C的一系列甲醇-乙腈溶剂混合物中进行的。结果表明：（i）亲核试剂中ϱN和β的含量随其组成的变化而变大，并表明过渡态键形成相对较先进，（ii）ofN和ϱsβ在溶剂组成中的最大尺寸。最大电离功率，加上正的交叉相互作用系数，表明S N2“同步推挽”类型的过渡状态，以及（iii）势能表面模型不稳定，无法预测过渡板岩向更像产品的过渡状态的变化，在这种状态下，键的形成更加进展，并且键断裂在将溶剂改变为离子化程度更高的一种离解能力时，它稍微先进一些。在这方面，量子力学模型优于势能表面模型。
• Amidines. VIII. A kinetic study of alcoholysis of N1-arenesulfonyl-N1,N2-diarylacetamidines.
  作者：Machiko ONO、Reiko TODORIKI、Shinzo TAMURA

  DOI：10.1248/cpb.39.558

  日期：——

  Alcoholysis of N1-Arenesulfonyl-N1, N2-diarylacetamidines (1-30) was studied kinetically. The rate of the reaction between the substrates and ethoxide ion depended on the electron-withdrawing resonance effect of the substituents on both the N1-aryl and N2-aryl groups to a similar extent. The rate of the neutral alcoholysis depended on the resonance effect of the N1-aryl substituent to a larger extent than in the former reaction, and depended hardly at all on the electron-releasing resonance effect of the N2-aryl substituent, showing that the reaction does not proceed by the solvolysis mechanism.A reaction mechanism is proposed in which the rate-determining attack of the nucleophile is accompanied by the concerted departure of the N-arylarenesulfonamide group.

  对 N1-壬磺酰基-N1，N2-二芳基乙酰胺（1-30）的醇解进行了动力学研究。底物与乙氧离子的反应速率在类似程度上取决于 N1 芳基和 N2 芳基上取代基的吸电子共振效应。与前一种反应相比，中性醇解反应的速率在更大程度上取决于 N1-芳基取代基的共振效应，而几乎不取决于 N2-芳基取代基的电子释放共振效应，这表明该反应不是通过溶解机理进行的。
• Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides
  作者：Banlai Ouyang、Yanxia Zheng、Yi Liu、Fei Liu、Juying Yao、Yiyuan Peng

  DOI：10.1016/j.tetlet.2018.09.001

  日期：2018.10

  A green and practical method for the synthesis of N-arylsulfonamides from chloramine salts and arylboronic acids is herein developed. The reaction proceeds readily in the presence of 5 mol% of CuI and 2.5 equiv. K2CO3 in water at room temperature, generating a variety of N-arylsulfonamides in moderate to good yields with good functional group tolerance.

  本文开发了一种从氯胺盐和芳基硼酸合成N-芳基磺酰胺的绿色实用方法。在5mol％的CuI和2.5当量的存在下，反应容易进行。室温下水中的K 2 CO 3，以中等至良好的产率生成各种N-芳基磺酰胺，并具有良好的官能团耐受性。