methyl 2-(S)-((tert-butoxycarbonyl)amino)-3-(2'-methoxyphenyl)propanoate

• 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 2-(S)-((tert-butoxycarbonyl)amino)-3-(2'-methoxyphenyl)propanoate
• 英文别名: (S)-methyl 2-(tert-butoxycarbonylamino)-3-(2-methoxyphenyl)propanoate；methyl (2S)-3-(2-methoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: VFRVFAOURFTPLD-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴苯甲醚 、 (R)-N-叔丁氧羰基-3-碘代丙氨酸甲酯 在 palladium diacetate 碘 、 锌 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 以13%的产率得到methyl 2-(S)-((tert-butoxycarbonyl)amino)-3-(2'-methoxyphenyl)propanoate
  参考文献：
  名称：

  α-氨基酸衍生的有机锌试剂与芳香族溴化物的Negishi交叉偶联反应

  摘要：

  描述了将Pd（OAc）2或Pd 2（dba）3与P（o- Tol）3结合使用的方法，描述了α-氨基酸衍生的有机锌碘化物与芳族溴的Negishi交叉偶联反应，得到取代的苯丙氨酸衍生物。在50°C的DMF中作为催化剂。使用Pd [P t Bu 3 ] 2作为催化剂，可获得相似的结果。芳基碘化物和溴化物之间显示出的反应性差异（ArI> ArBr）已用于不对称，正交保护的对亚苯撑双丙氨酸衍生物的简短合成中。

  DOI：

  10.1016/j.tet.2007.11.031

文献信息

• Negishi cross-coupling reactions of α-amino acid-derived organozinc reagents and aromatic bromides
  作者：Claire L. Oswald、Tomás Carrillo-Márquez、Lorenzo Caggiano、Richard F.W. Jackson

  DOI：10.1016/j.tet.2007.11.031

  日期：2008.1

  Negishi cross-coupling reaction of organozinc iodides derived from α-amino acids with aromatic bromides to give substituted phenylalanine derivatives is described, using either Pd(OAc)2 or Pd2(dba)3 in combination with P(o-Tol)3 as catalyst in DMF at 50 °C. Similar results are obtained using Pd[PtBu3]2 as catalyst. The difference in reactivity displayed between aryl iodides and bromides (ArI>ArBr) has been

  描述了将Pd（OAc）2或Pd 2（dba）3与P（o- Tol）3结合使用的方法，描述了α-氨基酸衍生的有机锌碘化物与芳族溴的Negishi交叉偶联反应，得到取代的苯丙氨酸衍生物。在50°C的DMF中作为催化剂。使用Pd [P t Bu 3 ] 2作为催化剂，可获得相似的结果。芳基碘化物和溴化物之间显示出的反应性差异（ArI> ArBr）已用于不对称，正交保护的对亚苯撑双丙氨酸衍生物的简短合成中。
• Concise Synthesis of Enantiomerically Pure Phenylalanine, Homophenylalanine, and Bishomophenylalanine Derivatives Using Organozinc Chemistry:  NMR Studies of Amino Acid-Derived Organozinc Reagents
  作者：Richard F. W. Jackson、Rebecca J. Moore、Charles S. Dexter、Jason Elliott、Charles E. Mowbray

  DOI：10.1021/jo981133u

  日期：1998.10.1

  Protected phenylalanines 23 (seven examples), homophenylalanines 7 (eight examples), and bishomophenylalanines 8 (seven examples) have been prepared by palladium-catalyzed coupling of the amino acid-derived organozinc reagents 13, 5, and 6, respectively, with aryl iodides. While the reactions of the zinc reagent 13 may be conducted in both THF and DMF as solvent, the results obtained in DMF are generally superior. In the case of the reagents 5 and 6 the results are far superior in DMF. NMR investigations on the structure of the zinc reagents 13 in THF suggest that there is strong intramolecular coordination of the urethane carbonyl group, whereas in DMF this interaction is completely suppressed.
• Much Improved Conditions for the Negishi Cross-Coupling of Iodoalanine Derived Zinc Reagents with Aryl Halides
  作者：Andrew J. Ross、Hannah L. Lang、Richard F. W. Jackson

  DOI：10.1021/jo902238n

  日期：2010.1.1

  A combination of Pd-2(dba)(3) and SPhos (1:2 molar ratio) is an excellent precatalyst for the Negishi cross-coupling of the serine-derived organozinc reagent 2 with aryl halides, including previously difficult ortho-substituted examples. In the case of meta- and para-substituted aryl halides, Pd-loadings of 0.5 mol % give satisfactory results. Use of 2-iodoaniline as substrate gives the lactam 12 in good yield.