N-(2-bromo-4-methylphenyl)-4-methylbenzenesulfonamide | 87995-68-4

• 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: N-(2-bromo-4-methylphenyl)-4-methylbenzenesulfonamide
• CAS: 87995-68-4
• 化学式: C₁₄H₁₄BrNO₂S
• mdl: MFCD00795506
• 分子量: 340.241
• InChiKey: UGVHBURDLZFBOE-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C(Solv: ethanol (64-17-5))
• 沸点：
  441.2±55.0 °C(Predicted)
• 密度：
  1.496±0.06 g/cm3(Predicted)

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：
  0.142
• 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：

  N-(2-bromo-4-methylphenyl)-4-methylbenzenesulfonamide 生成 4-氯-3-溴甲苯
  参考文献：
  名称：

  Convenient halodeamination and hydrodeamination of primary amines.

  摘要：

  Treatment of p-toluenesulfonamides of primary amines with 2 equiv of chloroamine at room temperature in the presence of base leads to reductive deamination. If excess chloroamine is present, the corresponding alkyl or aryl halides are obtained instead in good yields. Both reactions presumably proceed via tosylhydrazine and diazene intermediates; the course of the reaction is often governed by steric hindrance. Treatment of the isolated tosylhydrazine intermediate with base and chloroamine, bromine, or iodine also leads to the corresponding halides in very good yields.

  DOI：

  10.1021/jo00040a010
• 作为产物：
  描述：

  2-溴-4-甲基苯胺 以61%的产率得到
  参考文献：
  名称：

  HELLWINKEL, D.;LAEMMERZAHL, F.;HOFMANN, G., CHEM. BER., 1983, 116, N 10, 3375-3405

  摘要：

  DOI：

文献信息

• Directing-Group-Assisted Markovnikov-Selective Hydrothiolation of Styrenes with Thiols by Photoredox/Cobalt Catalysis
  作者：Qian Xiao、Hong Zhang、Jing-Hong Li、Jing-Xin Jian、Qing-Xiao Tong、Jian-Ji Zhong

  DOI：10.1021/acs.orglett.1c00999

  日期：2021.5.7

  organosulfur compounds, limited examples of transition-metal-catalyzed thiol-ene reactions have been reported. However, in this work, a directing-group-assisted hydrothiolation of styrenes with thiols by photoredox/cobalt catalysis is found to proceed smoothly to afford Markovnikov-type sulfides with excellent regioselectivity.

  与发达的自由基硫醇-烯反应获得反马尔可夫尼可夫型产物相反，烯烃的催化马尔可夫尼可夫选择性加氢硫醇化的研究非常有限。由于有机硫化合物对金属催化剂的催化剂中毒，已经报道了过渡金属催化的硫醇-烯反应的有限实例。然而，在这项工作中，发现通过光氧化还原/钴催化的苯乙烯与硫醇的直接基团辅助的氢硫醇化可以顺利进行，以提供具有优异的区域选择性的马尔可夫尼科夫型硫化物。
• Stereoselective Synthesis of Acyclic Tetrasubstituted Alkenes from Anilines by Dearomatization and Trimethylenemethane Cycloaddition
  作者：Lei Li、Qiuqin He、Renhua Fan

  DOI：10.1021/acs.orglett.1c03974

  日期：2022.1.14

  A method for stereoselective construction of acyclic all-carbon tetrasubstituted alkenes through insertion of nitrile-substituted trimethylenemethane into the aryl C–N bond in anilines via an aromaticity destruction-reconstruction process is reported. The process involves dearomatization, azo-[3 + 2] TMM cycloaddition and aromatization-triggered rearrangement.

  报道了一种通过芳香性破坏-重建过程将腈取代的三亚甲基甲烷插入苯胺中的芳基 C-N 键来立体选择性构建无环全碳四取代烯烃的方法。该过程涉及脱芳构化、偶氮-[3 + 2] TMM 环加成和芳构化引发的重排。
• Conformationally restricted functionalized heteroaromatics: a direct access to novel indoloindoles via Pd-mediated reaction
  作者：Bagineni Prasad、B. Yogi Sreenivas、D. Rambabu、G. Rama Krishna、C. Malla Reddy、K. Lalith Kumar、Manojit Pal

  DOI：10.1039/c2cc38342j

  日期：——

  A new, versatile and direct Pd-mediated method involving intramolecular cyclization of N-(2-iodoaryl)-N-(1-alkyl-1H-indol-2-yl)alkane/arene/heteroarene sulfonamide has been developed leading to a diverse and unique class of indolo[2,3-b]indoles for the potential inhibition of sirtuins.

  一种新的、多功能的直接钯介导方法已经开发，该方法涉及N-(2-碘芳基)-N-(1-烷基-1H-吲哚-2-基)烷烃/芳烃/杂芳烃磺酰胺的分子内环化，最终生成一种多样且独特的吲哚并[2,3-b]吲哚类化合物，这些化合物有潜力抑制去乙酰化酶（sirtuins）。
• Palladium-Catalyzed Synthesis of Selectively Substituted Phenanthridine Derivatives
  作者：Nicola Della Ca'、Elena Motti、Marta Catellani

  DOI：10.1002/adsc.200800512

  日期：2008.11.3

  Selectively substituted phenanthridine derivatives are obtained by a facile reaction of o-alkylated aryl iodides, o-bromoarenesulfonylanilines and activated olefins in the presence of palladium and norbornene as catalysts. The reaction takes place under mild conditions to give the products in satisfactory yields using readily available starting materials.

  在钯和降冰片烯作为催化剂的存在下，通过邻烷基化的芳基碘化物，邻溴代芳烃磺酰基苯胺和活化的烯烃的容易反应，获得选择性取代的菲啶衍生物。该反应在温和的条件下进行，使用容易获得的起始原料以令人满意的产率得到产物。
• Palladium‐Catalyzed Regioselective Synthesis of 1‐Hydroxycarbazoles Under Aerobic Conditions
  作者：So Won Youn、Young Ho Kim、Yoon Hyung Jo

  DOI：10.1002/adsc.201801265

  日期：2019.2

  A palladium‐catalyzed aerobic C−H amidation of N‐Ts‐2‐amino‐3′‐hydroxylbiaryls has been developed to afford a diverse range of 1‐hydroxycarbazoles with high regioselectivity and efficiency. This protocol benefits from operational simplicity, robustness, and sustainability with the use of ambient air as the sole terminal oxidant. Further elaboration of the products obtained from this process provides

  已开发出钯催化的N -Ts-2-氨基-3'-羟基联芳基的好氧CH H酰胺化反应，以提供具有高区域选择性和效率的各种1-羟基咔唑。通过使用环境空气作为唯一的终端氧化剂，该协议得益于操作简便，稳健性和可持续性。从该方法获得的产物的进一步精制提供了容易获得各种咔唑生物碱的方法，包括咔唑醌和双咔唑。提出了一种机制，涉及在2-氨基-3'-羟基联芳基的更受空间阻碍的C2'-位置的双指导基团辅助区域选择性CH活化。