N-cyclohexyl-4-methyl-N-(2-methyloctyl)benzenesulfonamide | 1071539-67-7

• 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-cyclohexyl-4-methyl-N-(2-methyloctyl)benzenesulfonamide
• CAS: 1071539-67-7
• 化学式: C₂₂H₃₇NO₂S
• 分子量: 379.607
• InChiKey: RTPYGYYWIPGWCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2-methyloctyl)cyclohexanamine 、 对甲苯磺酰氯 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 23.0h， 以346 mg的产率得到N-cyclohexyl-4-methyl-N-(2-methyloctyl)benzenesulfonamide
  参考文献：
  名称：

  Hydroaminoalkylation of Unactivated Olefins with Dialkylamines

  摘要：

  The intermolecular addition of the a-C-H bonds of unactivated dialkylamines to unactivated olefins in the presence of the chloro amido complex [TaCl3(NEt2)(2)](2) (2) is described. This process forms the branched insertion products in high yields (up to 96%) and selectivities, and a rare example of an intermolecular amine-olefin coupling reaction that does not require preactivation of either substrate. The reaction is shown to encompass the addition of the primary C-H bonds in linear- and branched-methylamines, as well as secondary C-H bonds in higher dialkylamines. The related chloroanilido complex [TaCl3(NMePh)(2)](2) (4) is also shown to catalyze the addition of N-alkyl-arylamines to olefins at temperatures as low as 90 degrees C. H-1 NMR spectroscopy, identification of the catalyst structure, and deuterium-labeling experiments all suggest that reactions catalyzed by 2 and 4 occur by turnover-limiting generation of an eta(2)-imine complex. These labeling studies also imply that more favorable partitioning of the eta(2)-imine complex toward reaction with alkene versus regeneration of the starting bis-amido complex accounts for the higher reactivity of the mixed halide amido catalyst versus a homoleptic amido complex.

  DOI：

  10.1021/ja806367e

文献信息

• TaMe₃Cl₂-Catalyzed Intermolecular Hydroaminoalkylation: A Simple Complex for Enhanced Reactivity and Expanded Substrate Scope
  作者：Zhengxing Zhang、Jean-Denys Hamel、Laurel L. Schafer

  DOI：10.1002/chem.201300992

  日期：2013.7.1

  Tantalizingly simple: The common organometallic starting material TaMe3Cl2 can be used for the catalytic CH functionalization reaction, hydroaminoalkylation. The substrate scope for this readily accessed compound includes unactivated terminal and internal alkenes, styrene derivatives, and both alkylaryl‐ and dialkyl secondary amines (see scheme).

  诱人简单：起始原料驯服常见的有机金属3氯2可用于催化Ç  ħ官能化反应，hydroaminoalkylation。这种易于获取的化合物的底物范围包括未活化的末端和内部烯烃，苯乙烯衍生物以及烷基芳基和二烷基仲胺（请参见方案）。