Methyl 2-amino-2-[[4-[tert-butyl(dimethyl)silyl]oxyphenyl]methyl]pent-4-enoate | 1372151-01-3

• 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: Methyl 2-amino-2-[[4-[tert-butyl(dimethyl)silyl]oxyphenyl]methyl]pent-4-enoate
• CAS: 1372151-01-3
• 化学式: C₁₉H₃₁NO₃Si
• 分子量: 349.546
• InChiKey: YMKULWCCNIHIRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酸烯丙酯 、 Methyl 2-amino-3-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]propanoate;hydrochloride 在 吡啶-2-甲醛 、 1,1'-双(二苯基膦)二茂铁 、 bis(acetylacetonate)nickel(II) 、 bis(η3-allyl-μ-chloropalladium(II)) 、 ammonium acetate 、 水 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以87%的产率得到Methyl 2-amino-2-[[4-[tert-butyl(dimethyl)silyl]oxyphenyl]methyl]pent-4-enoate
  参考文献：
  名称：

  Catalytic α-Allylation of Unprotected Amino Acid Esters

  摘要：

  Catalytic alpha-allylation of unprotected amino acid esters to produce alpha-quaternary alpha-allyl amino acid esters is reported. Catalytic loadings of picolinaldehyde and Ni(II) salts induce preferential reactivity at the enolizable alpha-carbon of amino acid esters over the free nitrogen with electrophilic palladium pi-allyl complexes. Fourteen examples are given. Additionally, the use of chiral ligands to access enantioenriched alpha-quaternary amino acid esters from racemic precursors is demonstrated by the enantioselective synthesis of alpha-allyl phenylalanine methyl ester from racemic phenylalanine methyl ester.

  DOI：

  10.1021/ol300665n

文献信息

• Catalytic α-Allylation of Unprotected Amino Acid Esters
  作者：Ping Fang、Mani Raj Chaulagain、Zachary D. Aron

  DOI：10.1021/ol300665n

  日期：2012.4.20

  Catalytic alpha-allylation of unprotected amino acid esters to produce alpha-quaternary alpha-allyl amino acid esters is reported. Catalytic loadings of picolinaldehyde and Ni(II) salts induce preferential reactivity at the enolizable alpha-carbon of amino acid esters over the free nitrogen with electrophilic palladium pi-allyl complexes. Fourteen examples are given. Additionally, the use of chiral ligands to access enantioenriched alpha-quaternary amino acid esters from racemic precursors is demonstrated by the enantioselective synthesis of alpha-allyl phenylalanine methyl ester from racemic phenylalanine methyl ester.