methyl N,N-dimethylphenylalaninate | 52893-40-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl N,N-dimethylphenylalaninate
• 英文别名: methyl 2-(dimethylamino)-3-phenylpropionate；2-Dimethylamino-3-phenylpropionsaeuremethylester；N,N-dimethyl-phenylalanine methyl ester；methyl (2S)-2-(dimethylamino)-3-phenylpropanoate；methyl 2-(dimethylamino)-3-phenylpropanoate
• CAS: 52893-40-0
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: ZQUSOVOPGJCBDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N,N-dimethylphenylalaninate 、 2-methyl-2-(pyridin-2-yl)propane-1,3-diamine 130.0 ℃ 、10.0 kPa 条件下， 反应 36.0h， 生成 rac-dimethyl{1-[5-methyl-5-(pyridin-2-yl)-1,4,5,6-tetrahydropyrimidin-2-yl]-2-phenylethylamine}
  参考文献：
  名称：

  Brunner, Henri; Maier, Reinhard J.; Zabel, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2001, vol. 56, # 10, p. 975 - 978

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基甘氨酸甲酯 在 potassium hydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 methyl N,N-dimethylphenylalaninate
  参考文献：
  名称：

  Controlling Selectivity by Controlling the Path of Trajectories

  摘要：

  Consideration of the role of dynamic trajectories in [1,2]- and [2,3]-sigmatropic rearrangements suggests a counterintuitive approach to controlling the selectivity. In our hypothesis, [2,3] selectivity can be promoted by reaction conditions that thermodynamically disfavor the [2,3] rearrangement step and thereby make the transition state later. The application of this idea has led to a successful prescription for dictating the selectivity in Stevens/Sommelet-Hauser rearrangements of ammonium ylides. A combination of kinetic isotope effects, crossover experiments, and computational dynamic trajectories support the idea that the selectivity is controlled through control of the path of trajectories.

  DOI：

  10.1021/jacs.5b08635

文献信息

• Palladium(II)-Catalyzed Remote <i>meta</i>-C–H Functionalization of Aromatic Tertiary Amines
  作者：Bo Wang、Yu Zhou、Niuniu Xu、Xiufang Xu、Xiaohua Xu、Zhong Jin

  DOI：10.1021/acs.orglett.9b00499

  日期：2019.3.15

  Pd(II)-catalyzed remote C–H olefination of aromatic tertiary amines was achieved with high meta selectivity. With the assistance of an elaborated template, C–H functionalization of unreactive aryl tertiary amines, hindered by the p−π conjugation between the lone-pair electrons of the nitrogen atom and the phenyl ring, was realized with high meta regioselectivity via a quaternary ammonium salt assembly. The results

  Pd（II）催化的芳族叔胺的远程C–H烯化具有很高的间位选择性。用一个详细模板的协助下，未反应的芳基叔胺的C-H官能化，阻碍通过氮原子与苯环的孤对电子之间的P-π共轭，用高实现元区域选择性通过季铵盐装配。结果表明，除了模板的距离和几何形状外，芳烃底物的构象在模板辅助的远程C–H功能化中也起着至关重要的作用。
• Nickel Photocatalyzed Reductive 1,4-Dicarbofunctionalization of 1,3-Enynes with <i>N</i>-Methylamines and Organohalides Enabled by Site-Selective C(sp³)–H Functionalization
  作者：Chaozhihui Cheng、Gui-Fen Lv、Shuang Wu、Yang Li、Jin-Heng Li

  DOI：10.1021/acs.orglett.3c01103

  日期：2023.6.16

  catalysis for 1,4-dicarbofunctionalization of 1,3-enynes with tertiary N-methylamines and organohalides to produce tetrasubstituted allenes is presented. This method enables the generation of the aminoalkyl C(sp3)-centered radicals by site selective cleavage of the N-methyl C(sp3)–H bonds in tertiary N-methylamines and is extended to alkyl bromides as the electrophilic terminating regents. Mechanistic

  提出了一种用于 1,3-烯炔与叔N-甲胺和有机卤化物的 1,4-二碳官能化以产生四取代丙二烯的协同镍和光氧化还原还原催化。该方法能够通过对 N-甲基叔胺中的N-甲基C(sp 3 )–H 键进行位点选择性裂解，生成以 C (sp 3 ) 为中心的氨基烷基自由基，并将其扩展为烷基溴作为亲电子终止试剂。机理研究表明该反应涉及自由基过程和Ni 0 /Ni I /Ni III催化循环。
• Novel Isomerization Reaction of <i>N</i>,<i>N</i>-Dimethyl-α-(methoxycarbonyl)-4-substituted- benzylammonium <i>N</i>-Methylides
  作者：Chen Zhang、Hiroto Ito、Yasuhiro Maeda、Naohiro Shirai、Shin-ichi Ikeda、Yoshiro Sato

  DOI：10.1021/jo981729h

  日期：1999.1.1

  Fluoride ion-induced desilylation of N,N-dimethyl-N-[(trimethylsilyl)methyl]-alpha-(methoxycarbonyl)- 4-substituted benzylammonium salts (7) gave two Stevens rearrangement products: methyl 3-(dimethylamino)-2-(4-substituted phenyl)propionates (13) from N-methylides 8, and methyl 3-(dimethylamino)-3-(4-substituted phenyl)propionates (15) from N-benzylides 10. Additional Stevens rearrangement products, methyl 2-(dimethylamino)-3-(4-substituted phenyl)propionates (16), were competitively formed from ylides 12 when the cesium fluoride used was not predried. The mechanism of the isomerization from methylides 8, which was initially generated, to 10 and 12 is discussed.
• RAZINA, T. L.;OGANDZHANYAN, S. M.;KOCHARYAN, S. T.;BABAYAN, A. T., ARM. XIM. ZH., 1982, 35, N 10, 644-648
  作者：RAZINA, T. L.、OGANDZHANYAN, S. M.、KOCHARYAN, S. T.、BABAYAN, A. T.

  DOI：——

  日期：——
• BABAYAN A. T.; KOCHARYAN S. T.; OGANDZHANYAN S. M., AJKAKAN KIMIAKAN AMSAGIR., ARM. XIM. ZH. <AUKZ-AN>, 1976, 29, HO 5, 403-4+
  作者：BABAYAN A. T.、 KOCHARYAN S. T.、 OGANDZHANYAN S. M.

  DOI：——

  日期：——