N-(1-(dimethyl(phenyl)silyl)-1-phenylethyl)-4-methylbenzenesulfonamide | 1283154-36-8

• 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-(1-(dimethyl(phenyl)silyl)-1-phenylethyl)-4-methylbenzenesulfonamide
• 英文别名: N-{1-[dimethyl(phenyl)silyl]-1-phenylethyl}-4-toluenesulfonamide；N-[1-[dimethyl(phenyl)silyl]-1-phenylethyl]-4-methylbenzenesulfonamide
• CAS: 1283154-36-8
• 化学式: C₂₃H₂₇NO₂SSi
• 分子量: 409.624
• InChiKey: RICKSKVRMXIOME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  对甲苯磺酰胺 以 四氢呋喃 为溶剂， 反应 15.5h， 生成 N-(1-(dimethyl(phenyl)silyl)-1-phenylethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Efficient Synthesis of α-Tertiary α-Silylamines from Aryl Sulfonylimidates via One-Pot, Sequential C–Si/C–C Bond Formations

  摘要：

  An efficient and flexible route for the synthesis of alpha-tertiary (alpha,alpha-dibranched) alpha-silylamines via sequential reactions of sulfonylimidates using readily available phenyldimethylsilyllithium and Grignard reagents is described. The procedure allows successive formation of C-Si/C-C bonds In a single flask.

  DOI：

  10.1021/ol301194e

文献信息

• Activation of the Si−B Linkage: Copper-Catalyzed Addition of Nucleophilic Silicon to Imines
  作者：Devendra J. Vyas、Roland Fröhlich、Martin Oestreich

  DOI：10.1021/ol200509c

  日期：2011.4.15

  quickly developed into a practical method to generate Cu−Si reagents. These silicon nucleophiles cleanly add to aldehyde-derived imine electrophiles to form α-silylated amines in protic media, and no carbon-to-nitrogen Brook-type rearrangement of the intermediate anion is observed. Aside from electron-withdrawing groups at the imine nitrogen atom, for example, SO2Tol and P(O)Ph2, previously delicate nitrogen

  通过铜催化的过渡金属化对Si-B键的激活迅速发展为一种生成Cu-Si试剂的实用方法。这些硅亲核试剂干净地添加到醛衍生的亚胺亲电试剂中，从而在质子介质中形成α-甲硅烷基化胺，并且未观察到中间阴离子的碳-氮布鲁克型重排。除了亚胺氮原子上的吸电子基团（例如SO 2 Tol和P（O）Ph 2）外，还可以耐受先前精密的氮取代基，例如苯基或二苯甲基。相同的协议还允许史无前例地添加代表酮的亚胺。
• Copper-Catalyzed Silylation of C(sp³)–H Bonds Adjacent to Amide Nitrogen Atoms
  作者：Jian-Jun Feng、Martin Oestreich

  DOI：10.1021/acs.orglett.8b01698

  日期：2018.7.20

  copper-catalyzed C–Si bond formation between N-halogenated amides and Si–B reagents is described. This oxidative coupling enables the silylation of C(sp3)–H bonds α to an amide nitrogen atom. The utility of the new method is demonstrated for sulfonamides, and N-chlorination with tBuOCl and C–H silylation employing CuSCN/4,4′-dimethoxy-2,2′-bipyridine as catalyst can be performed without purification of the

  描述了在N-卤代酰胺和Si-B试剂之间形成铜催化的C-Si键。这种氧化偶合使C（sp 3）–H键α与酰胺氮原子的甲硅烷基化。证明了该新方法对磺胺类药物的实用性，并且无需纯化N–即可进行以t BuOCl进行N-氯化和使用CuSCN / 4,4'-二甲氧基-2,2'-联吡啶作为催化剂进行C–H甲硅烷基化。 Cl中间体。
• Efficient Synthesis of α-Tertiary α-Silylamines from Aryl Sulfonylimidates via One-Pot, Sequential C–Si/C–C Bond Formations
  作者：Xiao-Jun Han、Ming Yao、Chong-Dao Lu

  DOI：10.1021/ol301194e

  日期：2012.6.1

  An efficient and flexible route for the synthesis of alpha-tertiary (alpha,alpha-dibranched) alpha-silylamines via sequential reactions of sulfonylimidates using readily available phenyldimethylsilyllithium and Grignard reagents is described. The procedure allows successive formation of C-Si/C-C bonds In a single flask.