methyl 3-(3,4-dihydroisoquinolin-2(1H)-yl)-2,2-dimethylpropanoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: methyl 3-(3,4-dihydroisoquinolin-2(1H)-yl)-2,2-dimethylpropanoate
• 英文别名: methyl 3-(3,4-dihydro-1H-isoquinolin-2-yl)-2,2-dimethylpropanoate
• 化学式: C₁₅H₂₁NO₂
• mdl: MFCD24884586
• 分子量: 247.337
• InChiKey: CMXSDWVHEKGNKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异丁酸甲酯 在 正丁基锂 、 2,6-二叔丁基-4-甲基吡啶 、 sodium cyanoborohydride 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 36.45h， 生成 methyl 3-(3,4-dihydroisoquinolin-2(1H)-yl)-2,2-dimethylpropanoate
  参考文献：
  名称：

  Preparation of Conformationally Restricted β^2,2- and β^2,2,3-Amino Esters and Derivatives Containing an All-Carbon Quaternary Center

  摘要：

  β-Amino acids are routinely incorporated into peptidic drugs to increase their stability and to incur conformational biases. However, the synthesis of highly substituted β-amino acids still represents a great challenge. A new approach to their preparation is reported involving a Vilsmeier-Haack reaction with nonaromatic carbon nucleophiles. The highly challenging preparation of contiguous tertiary and all-carbon quaternary centers was successfully used to generate several β(2,2,3)-amino esters, such as derivatives of homoproline, homoalanine, and homopipecolinic esters.

  DOI：

  10.1021/ol503432b

文献信息

• Preparation of Conformationally Restricted β^2,2- and β^2,2,3-Amino Esters and Derivatives Containing an All-Carbon Quaternary Center
  作者：Alexandre Romanens、Guillaume Bélanger

  DOI：10.1021/ol503432b

  日期：2015.1.16

  β-Amino acids are routinely incorporated into peptidic drugs to increase their stability and to incur conformational biases. However, the synthesis of highly substituted β-amino acids still represents a great challenge. A new approach to their preparation is reported involving a Vilsmeier-Haack reaction with nonaromatic carbon nucleophiles. The highly challenging preparation of contiguous tertiary and all-carbon quaternary centers was successfully used to generate several β(2,2,3)-amino esters, such as derivatives of homoproline, homoalanine, and homopipecolinic esters.