(Z)-1,4-bis[(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl]-2-bromo-2-butene | 195619-44-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: (Z)-1,4-bis[(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl]-2-bromo-2-butene
• 英文别名: (2R,5S)-2-[(Z)-2-bromo-4-[(2R,5S)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]but-2-enyl]-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazine
• CAS: 195619-44-4
• 化学式: C₂₂H₃₅BrN₄O₄
• 分子量: 499.448
• InChiKey: KRPYCMPDCKXQME-OBRZFWJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  86.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (Z)-1,4-bis[(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl]-2-bromo-2-butene 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex N-甲基吡咯烷酮 、 盐酸 、 三苯胂 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 17.0h， 生成 (Z)-(2R,7R)-2,7-Diamino-4-((E)-styryl)-oct-4-enedioic acid dimethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Alkenyl alpha,alpha'-Bridged Bis(glycines) using Palladium Promoted Substitution in the Bridge.

  摘要：

  Conformationally constrained cystine analogues have been synthesized which have an unsaturated four-carbon backbone-chain as a bridge between the alpha,alpha'-positions in two glycine units. Stereoselective synthesis of the cis and trans isomers of bis(glycines) with a 2'-butene bridge, and their 2'-bromo derivatives, is described. Palladium mediated coupling between the bromides and stannanes provided for carbo-substitution at the olefinic carbon in the bridge. N-Methyl-2-pyrrolidinone was an excellent solvent for this reaction when triphenylarsine was the ligand for palladium. Mild hydrolytic conditions furnished the methyl esters of the C-4-bridged bis(glycine) derivatives.

  DOI：

  10.3891/acta.chem.scand.51-0942
• 作为产物：
  描述：

  (S)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 、 (E)-1,2,4-Tribromobut-2-ene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以56%的产率得到(Z)-1,4-bis[(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl]-2-bromo-2-butene
  参考文献：
  名称：

  Stereoselective Synthesis of Alkenyl alpha,alpha'-Bridged Bis(glycines) using Palladium Promoted Substitution in the Bridge.

  摘要：

  Conformationally constrained cystine analogues have been synthesized which have an unsaturated four-carbon backbone-chain as a bridge between the alpha,alpha'-positions in two glycine units. Stereoselective synthesis of the cis and trans isomers of bis(glycines) with a 2'-butene bridge, and their 2'-bromo derivatives, is described. Palladium mediated coupling between the bromides and stannanes provided for carbo-substitution at the olefinic carbon in the bridge. N-Methyl-2-pyrrolidinone was an excellent solvent for this reaction when triphenylarsine was the ligand for palladium. Mild hydrolytic conditions furnished the methyl esters of the C-4-bridged bis(glycine) derivatives.

  DOI：

  10.3891/acta.chem.scand.51-0942