N-((R)-1-(4-methoxyphenyl)ethyl)pivalamide | 1202033-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-((R)-1-(4-methoxyphenyl)ethyl)pivalamide
• 英文别名: N-[(1R)-1-(4-methoxyphenyl)ethyl]-2,2-dimethylpropanamide
• CAS: 1202033-54-2
• 化学式: C₁₄H₂₁NO₂
• mdl: MFCD23094760
• 分子量: 235.326
• InChiKey: PDZFEDNHRSUAIX-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(1-(4-methoxyphenyl)vinyl)pivalamide 在 Rh[(nbd)((2S,2'S,3S,3'S)-BIBOP)]BF₄ 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-((R)-1-(4-methoxyphenyl)ethyl)pivalamide
  参考文献：
  名称：

  Novel, Tunable, and Efficient Chiral Bisdihydrobenzooxaphosphole Ligands for Asymmetric Hydrogenation

  摘要：

  A series of novel, efficient, air-stable, and tunable chiral bisdihydrobenzooxaphosphole ligands (BIBOPs) were developed for rhodium-catalyzed hydrogenations of various functionalized olefins such as alpha-arylenamides, alpha-(acylamino)acrylic acid derivatives, beta-(acylamino)acrylates, and dimethyl itaconate with excellent enantioselectivities (up to 99% ee) and reactivities (up to 2000 TON).

  DOI：

  10.1021/ol9025815

文献信息

• A Versatile and Practical Solvating Agent for Enantioselective Recognition and NMR Analysis of Protected Amines
  作者：Daniel P. Iwaniuk、Christian Wolf

  DOI：10.1021/jo101426a

  日期：2010.10.1

  The 3,5-dinitrobenzoyl-derived 1-naphthylethyl amide 3 is an attractive CSA for NMR analysis of protected amines. It is readily prepared in a single step and combines practical resolution of diastereomeric complexes due to signal sharpness and effective signal separation. Crystallographic analysis shows that 3 forms a chiral cleft that can selectively bind one enantiomer of a substrate through hydrogen bonding, pi-pi stacking, and CH/pi interactions. The enantioselective complex formation causes strong upfield shifts in the H-1 NMR spectrum even in the presence of only 5 mol % of 3.
• Novel, Tunable, and Efficient Chiral Bisdihydrobenzooxaphosphole Ligands for Asymmetric Hydrogenation
  作者：Wenjun Tang、Bo Qu、Andrew G. Capacci、Sonia Rodriguez、Xudong Wei、Nizar Haddad、Bikashandarkoil Narayanan、Shengli Ma、Nelu Grinberg、Nathan K. Yee、Dhileep Krishnamurthy、Chris H. Senanayake

  DOI：10.1021/ol9025815

  日期：2010.1.1

  A series of novel, efficient, air-stable, and tunable chiral bisdihydrobenzooxaphosphole ligands (BIBOPs) were developed for rhodium-catalyzed hydrogenations of various functionalized olefins such as alpha-arylenamides, alpha-(acylamino)acrylic acid derivatives, beta-(acylamino)acrylates, and dimethyl itaconate with excellent enantioselectivities (up to 99% ee) and reactivities (up to 2000 TON).