1,2-dichloro-4-tosylbenzene | 143538-80-1

• 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: 1,2-dichloro-4-tosylbenzene
• 英文别名: 1,2-Dichloro-4-(4-methylbenzene-1-sulfonyl)benzene；1,2-dichloro-4-(4-methylphenyl)sulfonylbenzene
• CAS: 143538-80-1
• 化学式: C₁₃H₁₀Cl₂O₂S
• 分子量: 301.193
• InChiKey: CRQMLYUBJVJHHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  445.4±45.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  1,2-dichloro-4-tosylbenzene 在 potassium permanganate 、 potassium hydrogencarbonate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以88%的产率得到4-(3,4-dichlorophenyl)sulfonylbenzoic acid
  参考文献：
  名称：

  Kepner-Tregoe Decision Analysis as a Tool To Aid Route Selection. Part 2. Application to AZD7545, a PDK Inhibitor

  摘要：

  Kepner-Tregoe decision analysis was formally used as an aid to route selection, as outlined in the preceding paper. Over 40 paper routes were assessed for suitability for both immediate and longer term manufacture of AZD7545, a compound in the early stages of development. Eight routes were then investigated in fall in the laboratory, and a further four in part, over a period of 3-4 months. From this exercise, the preferred long-term manufacturing route was identified before the first pilot scale manufacture had been completed. This route selection exercise worked well in this case where a large number of potential routes had to be considered using limited resources. It was also an effective means of bringing some long-term manufacturing issues to the fore at an early stage in development.

  DOI：

  10.1021/op800033c
• 作为产物：
  描述：

  对甲苯磺酰叠氮 、 邻二氯苯 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到1,2-dichloro-4-tosylbenzene
  参考文献：
  名称：

  磺酰叠氮化物中S–N键的区域特异性裂解：磺酰基供体

  摘要：

  磺酰叠氮化物已被广泛用作合成化学中的磺酰氨基，重氮和叠氮基供体，以及全氮1,3-偶极供体。在这里，磺酰叠氮化物被用作有效的磺酰供体，这是非常不寻常的。研究了三氟甲磺酸诱导的由磺酰叠氮化物形成的磺酰阳离子反应性物质，并首次用于偶联各种灭活的芳烃，从而在环境温度下制备砜。

  DOI：

  10.1021/acs.joc.8b03046

文献信息

• A Convenient Synthesis of 2-Nitrophenols from 1,2-Dichlorobenzenes
  作者：Joseph Zilberman、David Ioffe、Igal Gozlan

  DOI：10.1055/s-1992-26192

  日期：——

  Aromatic nucleophilic substitution of 1,2-dichlorobenzenes 1 possessing a strong electron-withdrawing group in the 4-position with a nitrite ion give the corresponding 2-nitrophenols 5.

  具有强吸电子基团的4-位1,2-二氯苯1与亚硝酸根离子进行亲核芳香取代反应，得到相应的2-硝基酚5。
• An efficient heterogeneous copper fluorapatite (CuFAP)-catalysed oxidative synthesis of diaryl sulfone under mild ligand- and base-free conditions
  作者：Rohit B. Kamble、Santosh S. Chavan、Gurunath Suryavanshi

  DOI：10.1039/c8nj04845b

  日期：——

  A simple, eco-friendly and efficient method for the synthesis of unsymmetrical diaryl sulfones using heterogeneous copper fluorapatite (CuFAP)-catalysed coupling of aryl sulfonic acid and phenyl boronic acid has been developed with good to excellent yields without use of any ligand, base or co-catalyst. Broad substrate scope and gram scale operations are the important features of this method.

  已经开发了一种简单，环保，高效的方法，该方法使用氟磺酸铜异相（CuFAP）催化的芳基磺酸和苯基硼酸的偶合反应合成不对称二芳基砜，且收率高至优异，而无需使用任何配体，碱或助催化剂。广泛的底物范围和克规模的操作是该方法的重要特征。
• Copper catalyzed synthesis of unsymmetrical diaryl sulfones from an arenediazonium salt and sodium p-toluenesulfinate
  作者：Sitaram Haribhau Gund、Radheshyam Suresh Shelkar、Jayashree Milind Nagarkar

  DOI：10.1039/c5ra10291j

  日期：——

  Aryl sulfones have been synthesized by the reaction of sodium p-toluenesulfinate and arenediazonium salts using a CuI catalyzed homogeneous system.

  芳基磺酮是通过钠对甲基磺酸钠和芳基重氮盐在CuI催化的均相体系中反应合成的。
• Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: synthesis of (un)symmetrical diaryl/alkyl aryl sulfones
  作者：Ruchi Chawla、Lal Dhar S. Yadav

  DOI：10.1039/c9ob00864k

  日期：——

  We disclose herein the first transition-metal- and external oxidant/reductant-free visible-light-mediated synthesis of (un)symmetrical diaryl/alkyl aryl sulfones from arenediazonium tetrafluoroborates and sodium sulfinates using eosin Y as an organic photoredox catalyst. The utilization of visible light as an inexpensive and ecosustainable energy source, operational simplicity, ambient temperature

  我们在此公开了使用曙红Y作为有机光氧化还原催化剂，由四氟硼酸芳族重氮鎓和亚磺酸钠从（无）对称二芳基/烷基芳基砜的第一过渡金属和外部无氧化剂/还原剂的可见光介导的合成。利用可见光作为廉价且生态可持续的能源，操作简便，环境温度和乙腈水溶液中的清洁反应是已开发方案的主要特征。所需的砜也可以通过一锅，两步法直接从苯胺和亚磺酸盐合成，产率高到极好。
• Huisman et al., Recueil des Travaux Chimiques des Pays-Bas, 1958, vol. 77, p. 103,112, 114
  作者：Huisman et al.

  DOI：——

  日期：——