methyl 3-phenyl-2-(picolinamido)propanoate | 1160854-49-8

• 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 3-phenyl-2-(picolinamido)propanoate
• 英文别名: Methyl 3-phenyl-2-(pyridine-2-carbonylamino)propanoate
• CAS: 1160854-49-8
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: DCKANOPCZIAODB-UHFFFAOYSA-N

物化性质

• 沸点：
  520.4±45.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-phenyl-2-(picolinamido)propanoate 在 lithium hydroxide monohydrate 作用下， 以 甲醇 为溶剂， 生成 3-phenyl-2-[(pyridine-2-carbonyl)-amino]-propionic acid
  参考文献：
  名称：

  Trifunctional N,N,O-Terdentate Amido/Pyridyl Carboxylate Ligated Pd(II) Complexes for Heck and Suzuki Reactions

  摘要：

  Trifunctional N,N,O-terdentate amido/pyridyl carboxylate Pd(II) complexes were highly active and stable phosphine-free catalysts for Heck and room-temperature Suzuki reactions with high turnover numbers tip to ca. 10(4).

  DOI：

  10.1021/jo900361c
• 作为产物：
  描述：

  D-苯丙氨酸1.1-二甲基乙基酯 在 氯甲酸乙酯 、 三乙胺 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 41.5h， 生成 methyl 3-phenyl-2-(picolinamido)propanoate
  参考文献：
  名称：

  Heterocycle Synthesis via Direct C–H/N–H Coupling

  摘要：

  A method for five- and six-membered heterocycle formation by palladium-catalyzed C-H/N-H coupling is presented. The method employs a picolinamide directing group, PhI(OAc)(2) oxidant, and toluene solvent at 80-120 degrees C. Cyclization is effective for sp(2) as well as aliphatic and benzylic sp(3) C-H bonds.

  DOI：

  10.1021/ja210959p

文献信息

• Iron-Catalyzed Oxidative CH/CH Cross-Coupling: An Efficient Route to α-Quaternary α-Amino Acid Derivatives
  作者：Kaizhi Li、Guangying Tan、Jingsheng Huang、Feijie Song、Jingsong You

  DOI：10.1002/anie.201306181

  日期：2013.12.2

  Fully loaded: A coordinating activation strategy has been developed to furnish α‐quaternary α‐amino acids through the iron(III)‐catalyzed oxidative functionalization of α‐C(sp3)H bonds of α‐tertiary α‐amino acid esters. The reaction exhibits a broad substrate scope for both α‐amino acids and nucleophiles (Nu) as well as good functional‐group tolerance (see scheme, DTBP=di‐tert‐butyl peroxide, DCE=1

  满负荷：已开发出协调的活化策略，以通过铁（III）催化的α-叔α-氨基酸酯的α-C（sp 3）H键的氧化功能化来提供α-季级α-氨基酸。该反应对α-氨基酸和亲核试剂（Nu）均具有广泛的底物范围，并且具有良好的官能团耐受性（参见方案，DTBP =过氧化二叔丁基，DCE = 1,2-二氯乙烷）。
• Mild Pd-Catalyzed Aminocarbonylation of (Hetero)Aryl Bromides with a Palladacycle Precatalyst
  作者：Stig D. Friis、Troels Skrydstrup、Stephen L. Buchwald

  DOI：10.1021/ol502014b

  日期：2014.8.15

  A palladacyclic precatalyst is employed to cleanly generate a highly active XantPhos-ligated Pd-catalyst. Its use in low temperature aminocarbonylations of (hetero)aryl bromides provides access to a range of challenging products in good to excellent yields with low catalyst loading and only a slight excess of CO. Some products are unattainable by traditional carbonylative coupling.