methyl N-(2-iodobenzylidene)-phenylglycinate

• 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-(2-iodobenzylidene)-phenylglycinate
• 化学式: C₁₆H₁₄INO₂
• 分子量: 379.197
• InChiKey: DFXWZSZOSXUGNH-WOJGMQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl N-(2-iodobenzylidene)-phenylglycinate 在 palladium diacetate 、 2-叔丁基-1,1,3,3-四甲基胍 、 thallium(I) acetate 、 三苯基膦 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 61.5h， 生成 (1R,3S,9bS)-5-Oxo-3-phenyl-2,3,5,9b-tetrahydro-1H-pyrrolo[2,1-a]isoindole-1,3-dicarboxylic acid 1-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester 3-methyl ester
  参考文献：
  名称：

  Sequential and cascade 1,3-dipolar cycloaddition-palladium catalysed carbonylation-cyclisation reactions. Diastereospecific and homochiral processes

  摘要：

  Combinations of imine --> azomethine ylide --> cycloaddition cascades with Pd(0) catalysed cyclisation-carbonylation forming 5- and 6-membered lactams in sequential reactions are described and both diastereospecific and homochiral examples are provided, The azomethine ylides can be generated either via thermal 1,2-prototropy or metal ion catalysis at ambient temperature. The former sequence has been combined with the Pd(0) catalysed cascade into a one-pot protocol.

  DOI：

  10.1016/0040-4020(94)00956-u
• 作为产物：
  描述：

  2-碘苯甲醛 、 苯基甘氨酸甲酯盐酸盐 在 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以91%的产率得到methyl N-(2-iodobenzylidene)-phenylglycinate
  参考文献：
  名称：

  Sequential and cascade 1,3-dipolar cycloaddition-palladium catalysed carbonylation-cyclisation reactions. Diastereospecific and homochiral processes

  摘要：

  Combinations of imine --> azomethine ylide --> cycloaddition cascades with Pd(0) catalysed cyclisation-carbonylation forming 5- and 6-membered lactams in sequential reactions are described and both diastereospecific and homochiral examples are provided, The azomethine ylides can be generated either via thermal 1,2-prototropy or metal ion catalysis at ambient temperature. The former sequence has been combined with the Pd(0) catalysed cascade into a one-pot protocol.

  DOI：

  10.1016/0040-4020(94)00956-u

文献信息

• Sequential and cascade 1,3-dipolar cycloaddition-palladium catalysed carbonylation-cyclisation reactions. Diastereospecific and homochiral processes
  作者：Ronald Grigg、Visuanathar Sridharan、Selvaratnam Suganthan、Andrew W Bridge

  DOI：10.1016/0040-4020(94)00956-u

  日期：1995.1

  Combinations of imine --> azomethine ylide --> cycloaddition cascades with Pd(0) catalysed cyclisation-carbonylation forming 5- and 6-membered lactams in sequential reactions are described and both diastereospecific and homochiral examples are provided, The azomethine ylides can be generated either via thermal 1,2-prototropy or metal ion catalysis at ambient temperature. The former sequence has been combined with the Pd(0) catalysed cascade into a one-pot protocol.