4-methyl-N-(2-methyl-1-phenylpropyl)benzenesulfonamide | 110871-37-9

• 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: 4-methyl-N-(2-methyl-1-phenylpropyl)benzenesulfonamide
• CAS: 110871-37-9
• 化学式: C₁₇H₂₁NO₂S
• 分子量: 303.425
• InChiKey: BEKUUDPBSKMPRV-UHFFFAOYSA-N

物化性质

• 熔点：
  136.5-138 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  437.2±48.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲苯磺酰氯 在 copper(II) tetrafluroborate hexahydrate 、 盐酸羟胺 、 potassium carbonate 、 三乙胺 、 (1R,2R)-N,N'-di(2',3',4',5',6'-pentafluorobenzylidene)-1,2-diaminocyclohexane 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 56.5h， 生成 4-methyl-N-(2-methyl-1-phenylpropyl)benzenesulfonamide
  参考文献：
  名称：

  基于羟胺的胺化试剂的非定向，Cu催化的sp3 C–H胺化：催化和机理研究

  摘要：

  This work demonstrates the use of hydroxyl amine-based amination reagents RSO2NH-OAc for the nondirected, Cu-catalyzed amination of benzylic C-H bonds. The amination reagents can be prepared on a gram scale, are benchtop stable, and provide benzylic C-H amination products with up to 86% yield. Mechanistic studies of the established reactivity with toluene as substrate reveal a ligand-promoted, Cu-catalyzed mechanism proceeding through Ph-CH2(NTsOAc) as a major intermediate. Stoichiometric reactivity of Ph-CH2(NTsOAc) to produce Ph-CH2-NHTs suggests a two-cycle, radical pathway for C-H amination, in which the decomposition of the employed diimine ligands plays an important role.

  DOI：

  10.1021/acs.organomet.7b00003

文献信息

• A new manganese-mediated, cobalt-catalyzed three-component synthesis of (diarylmethyl)sulfonamides
  作者：Antoine Pignon、Erwan Le Gall、Thierry Martens

  DOI：10.3762/bjoc.10.39

  日期：——

  The synthesis of (diarylmethyl)sulfonamides and related compounds by a new manganese-mediated, cobalt-catalyzed three-component reaction between sulfonamides, carbonyl compounds and organic bromides is described. This organometallic Mannich-like process allows the formation of the coupling products within minutes at room temperature. A possible mechanism, emphasizing the crucial role of manganese is proposed.

  描述了一种新的锰介导、钴催化的三组分反应，通过磺胺酰胺、羰基化合物和有机溴化物合成（二芳基甲基）磺胺酰胺及相关化合物。这种有机金属曼尼希类过程允许在室温下在几分钟内形成偶联产物。提出了一个可能的机制，强调了锰的关键作用。
• Reactions with aziridines - 39
  作者：Andreas Onistschenko、Berthold Buchholz、Helmut Stamm

  DOI：10.1016/s0040-4020(01)89990-7

  日期：1987.1

  Reaction of activated 2,2-dimethylaziridines with Grignard reagents RMgHal in boiling THF can yield the products of normal aziridine ring opening, the rearranged opening products , and the methallylamides (isomers of ). The product distribution depends on R, Hal, and experimental conditions, and very strongly on the nature of the activating group A. It is shown that is opened (reversibly for A = sulfonyl)

  活化的2，2-二甲基氮丙啶与Grignard试剂RMgHal在沸腾的THF中反应，可以生成正常氮丙啶开环的产物，重排的开环产物和甲基烯丙酰胺（的异构体）。产物分布取决于R，哈尔和实验条件，和非常强烈的活化基团A.结果表明的性质被打开（可逆地为A =磺酰基）形成通过Hal的路易斯酸辅助攻击θ在的叔碳（被Hal异常开口θ）。证据表明，以及来自该中间体。
• Zinc(II)-Catalyzed Addition of Grignard Reagents to Ketones
  作者：Manabu Hatano、Orie Ito、Shinji Suzuki、Kazuaki Ishihara

  DOI：10.1021/jo100563p

  日期：2010.8.6

  The addition of organometallic reagents to carbonyl compounds has become a versatile method for synthesizing tertiary and secondary alcohols via carbon−carbon bond formation. However, due to the lack of good nucleophilicity or the presence of strong basicity of organometallic reagents, the efficient synthesis of tertiary alcohols from ketones has been particularly difficult and, thus, limited. We recently

  向羰基化合物中添加有机金属试剂已成为通过碳-碳键形成合成叔醇和仲醇的通用方法。然而，由于缺乏良好的亲核性或存在有机金属试剂的强碱性，由酮有效地合成叔醇特别困难并且因此受到限制。我们最近使用ZnCl 2，Me 3 SiCH 2开发了格氏试剂（RMgX：R =烷基，芳基； X = Cl，Br，I），对酮进行了高效的催化烷基化和芳基化反应MgCl和LiCl，可有效减少有问题的副反应。原则上，对于加成羰基化合物，RMgBr和RMgI的反应性不如RMgCl。因此，这种新颖的方法与均相催化的ZnCl 2 ·我3 SICH 2 MgCl·LiCl是相当有吸引力的，因为RMgBr和RMGI，其易于制备和/或可商购的，如RMgCl，可以成功地应用。除酮和醛以外，醛亚胺也有效地用于该催化反应，并以高收率获得了相应的仲胺。关于β-甲硅烷基效应和盐效应的机理细节，原位制备[R（Me 3 SiCH 2）2 Zn] -
• Radical Addition of Ethers to Imines Initiated by Dimethylzinc
  作者：Ken-ichi Yamada、Hidetaka Fujihara、Yasutomo Yamamoto、Yoshihisa Miwa、Tooru Taga、Kiyoshi Tomioka

  DOI：10.1021/ol0266572

  日期：2002.10.1

  Ethers undergo addition to imines in the presence of dimethylzinc and air through a radical process. [reaction: see text]

  醚在二甲基锌和空气存在下通过自由基过程加成亚胺。[反应：看文字]
• Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to CN double bonds
  作者：Fabien Cougnon、Laurence Feray、Samantha Bazin、Michèle P. Bertrand

  DOI：10.1016/j.tet.2007.09.014

  日期：2007.11

  Diethylzinc-mediated radical addition to CN bonds was investigated in the presence of phenylorganotellurium compounds as radical precursors. As group transfer agents, secondary alkyl phenyl tellurides were shown to be about twice as reactive as the corresponding alkyl iodides towards ethyl radical. Their use was proven to be advantageous regarding both chemoselectivity and yield. The replacement of

  在苯基有机碲化合物作为自由基前体的存在下，研究了二乙基锌介导的向CN键的自由基加成反应。作为基团转移剂，仲烷基苯基碲化物的反应活性约为相应的烷基碘对乙基的两倍。事实证明，它们的使用在化学选择性和产率方面都是有利的。用二甲基锌代替二乙基锌在这些反应中没有优势。