ditert-butyl (2S)-4-(dimethylaminomethylidene)-5-oxopyrrolidine-1,2-dicarboxylate | 144331-20-4

• 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: ditert-butyl (2S)-4-(dimethylaminomethylidene)-5-oxopyrrolidine-1,2-dicarboxylate
• CAS: 144331-20-4
• 化学式: C₁₇H₂₈N₂O₅
• 分子量: 340.42
• InChiKey: RMMJZOZPRBKLQO-LBPRGKRZSA-N

物化性质

• 沸点：
  401.3±55.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ditert-butyl (2S)-4-(dimethylaminomethylidene)-5-oxopyrrolidine-1,2-dicarboxylate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 生成 di-tert-butyl (S)-4-methylene-5-oxopyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of amino acid conjugates to 2-imino-3-methylene-5-carboxypyrrolidine and 2-imino-3-methylene-6-carboxypiperidine

  摘要：

  The four stereomers of 2-imino-3-methylene-5-L(carboxy-L-valyl)pyrrolidine, a bacterial metabolite that is inhibitory to the fire blight bacterium Erwinia amylovora, were synthesised and compared for antibacterial activity. Several alternative amino acid conjugates with L,L-stereochemistry were also prepared, and the synthesis was extended to 3-methylenepiperidine-6-L-carboxylic acid and a selection of 2-imino-3-methylenepiperidine-6-L-carboxy-L-amino acid conjugates. All synthetic amino acid conjugates (L,L-stereomers) were inhibitory to the growth of E. amylovora. The likely participation of the conjugated iminomethylene moiety as a Michael acceptor is implicated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.128
• 作为产物：
  描述：

  三(二甲氨基)甲烷 、 (S)-N-叔丁氧羰基-2-吡咯烷酮-5-甲酸叔丁酯 以 乙二醇二甲醚 为溶剂， 生成 ditert-butyl (2S)-4-(dimethylaminomethylidene)-5-oxopyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of amino acid conjugates to 2-imino-3-methylene-5-carboxypyrrolidine and 2-imino-3-methylene-6-carboxypiperidine

  摘要：

  The four stereomers of 2-imino-3-methylene-5-L(carboxy-L-valyl)pyrrolidine, a bacterial metabolite that is inhibitory to the fire blight bacterium Erwinia amylovora, were synthesised and compared for antibacterial activity. Several alternative amino acid conjugates with L,L-stereochemistry were also prepared, and the synthesis was extended to 3-methylenepiperidine-6-L-carboxylic acid and a selection of 2-imino-3-methylenepiperidine-6-L-carboxy-L-amino acid conjugates. All synthetic amino acid conjugates (L,L-stereomers) were inhibitory to the growth of E. amylovora. The likely participation of the conjugated iminomethylene moiety as a Michael acceptor is implicated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.128

文献信息

• Combinatorial Synthesis of Acacen-Type Ligands and Their Coordination Compounds
  作者：Urša Tomažin、Uroš Grošelj、Marta Počkaj、Franc Požgan、Bogdan Štefane、Jurij Svete

  DOI：10.1021/acscombsci.7b00027

  日期：2017.6.12

  transamination between six primary diamines and eight enaminones. The bis-enaminone products were used as tetradentate ligands for coordination of copper(II), nickel(II), cobalt(II), and palladium(II). Dependence of the preferred E- or Z-configuration of the enaminone ligand on the α-substituent of the enaminone moiety in solution was determined by NMR and confirmed by X-ray diffraction. The copper(II) complexes

  开发了一种高度模块化的合成方法，用于制备阿拉伯胶型配体及其配位化合物。通过在六个伯二胺和八个烯胺酮之间进行组合酸催化的氨基转移反应，合成了一系列46种acacen型配体。双烯胺产品用作四齿配体，用于配位铜（II），镍（II），钴（II）和钯（II）。通过NMR确定溶液中烯胺酮配体的优选E-或Z-构型对烯胺酮部分的α-取代基的依赖性，并通过X射线衍射证实。测试了铜（II）配合物在3 + 2偶氮甲亚胺亚胺成丙酸甲酯的环加成反应中作为催化剂的适用性。