2,3-dimethyl-N-phenylbutanamide | 1177010-13-7

• 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: 2,3-dimethyl-N-phenylbutanamide
• 英文别名: (R)-N-phenyl-2,3-dimethylbutanamide；(2R)-2,3-dimethyl-N-phenylbutanamide
• CAS: 1177010-13-7
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: JXNXRMCFWMJWGV-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-甲基-2-亚甲基-丁酸 在 4-二甲氨基吡啶 、 C₃₂H₁₂BF₂₄^(1-)*C₅₄H₇₁IrNP⁽¹⁺⁾ 、 氢气 、 caesium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 2,3-dimethyl-N-phenylbutanamide
  参考文献：
  名称：

  α取代丙烯酸的催化的对映选择性氢化由铱配合物的手性螺胺膦配体

  摘要：

  高活性：与手性螺环氨基膦配体的铱络合物的合成和作为催化剂用于α-取代的丙烯酸的不对称氢化（参见方案）施用。该复合物具有高活性的催化剂，显示出6000 h最多的周转频率-1，并且催化剂载量可减少到0.01％（摩尔）。

  DOI：

  10.1002/anie.201204363

文献信息

• Asymmetric Markovnikov Hydroaminocarbonylation of Alkenes Enabled by Palladium-Monodentate Phosphoramidite Catalysis
  作者：Ya-Hong Yao、Hui-Yi Yang、Ming Chen、Fei Wu、Xing-Xing Xu、Zheng-Hui Guan

  DOI：10.1021/jacs.0c11249

  日期：2021.1.13

  n of alkenes with anilines has been developed for the atom-economical synthesis of 2-substituted propanamides bearing an α-stereocenter. A novel phosphoramidite ligand L16 was discovered which exhibited very high reactivity and selectivity in the reaction. This asymmetric Markovnikov hydroaminocarbonylation employs readily available starting materials and tolerates a wide range of functional groups

  已经开发了钯催化的烯烃与苯胺的不对称马尔科夫尼科夫氢氨基羰基化反应，用于原子经济合成带有 α-立体中心的 2-取代丙酰胺。发现了一种新的亚磷酰胺配体 L16，它在反应中表现出非常高的反应性和选择性。这种不对称 Markovnikov 氢氨基羰基化使用容易获得的起始材料并耐受范围广泛的官能团，从而为在环境条件下区域选择性和对映选择性合成 2-取代丙酰胺提供了一种简便而直接的方法。机理研究表明，该反应通过钯氢化物途径进行。
• Enantioselective Friedel–Crafts reactions of ethenetricarboxylates and substituted pyrroles and furans and intramolecular reaction of benzene derivatives
  作者：Shoko Yamazaki、Shinichi Kashima、Taiki Kuriyama、Yuko Iwata、Tsumoru Morimoto、Kiyomi Kakiuchi

  DOI：10.1016/j.tetasy.2009.05.016

  日期：2009.6

  Compared to enantioselective Friedel-Crafts reactions of indoles, reactions of alkylidene malonates with monocyclic aromatic compounds generally proceed with low enantioselectivity. The Friedel-Crafts reactions of ethenetricarboxylates 1 and monocyclic heteroaromatic compounds, such as substituted pyrroles and furans were investigated. The reaction of 1 with 2,4-dimethylpyrrole in the presence of a chiral bis-oxazoline-copper(II) complex (10 mol %) in tetrahydrofuran at room temperature gave alkylated products in up to 72% ee. The reaction of 1 with 2-substituted furans gave alkylated products in 46-62% ee. The absolute stereochemistry of the furan Friedel-Crafts product 7e was determined by transformation to the known 2,3-dimethylbutyric acid. The intramolecular reaction of benzene derivatives gave cyclized products up to 56% ee. (C) 2009 Elsevier Ltd. All rights reserved.
• Enantioselective Hydrogenation of α-Substituted Acrylic Acids Catalyzed by Iridium Complexes with Chiral Spiro Aminophosphine Ligands
  作者：Shou-Fei Zhu、Yan-Bo Yu、Shen Li、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1002/anie.201204363

  日期：2012.8.27

  Highly active: Iridium complexes with chiral spiro aminophosphine ligands were synthesized and applied as catalysts for the asymmetric hydrogenation of α‐substituted acrylic acids (see scheme). The complexes were highly active catalysts, showing turnover frequencies of up to 6000 h−1, and catalyst loadings could be reduced to 0.01 mol %.

  高活性：与手性螺环氨基膦配体的铱络合物的合成和作为催化剂用于α-取代的丙烯酸的不对称氢化（参见方案）施用。该复合物具有高活性的催化剂，显示出6000 h最多的周转频率-1，并且催化剂载量可减少到0.01％（摩尔）。