1,6-bis-((2S,5R)-2,5-dihydro-2-isopropyl-3,6-dimethoxy-5-pyrazinyl)hexa-2,4-diyne | 195206-38-3

• 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: 1,6-bis-((2S,5R)-2,5-dihydro-2-isopropyl-3,6-dimethoxy-5-pyrazinyl)hexa-2,4-diyne
• 英文别名: (2R,5S)-2-[6-[(2R,5S)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]hexa-2,4-diynyl]-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazine
• CAS: 195206-38-3
• 化学式: C₂₄H₃₄N₄O₄
• 分子量: 442.558
• InChiKey: JEXABKXLONTQJA-ZRNYENFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1,6-bis-((2S,5R)-2,5-dihydro-2-isopropyl-3,6-dimethoxy-5-pyrazinyl)hexa-2,4-diyne 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以88%的产率得到(2R,9R)-2,9-Diamino-deca-4,6-diynedioic acid dimethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Alkynylglycines and alpha,alpha'-Alkynyl-Bridged Bis(glycines).

  摘要：

  Pd-CuI catalysis has been used to effect carbo-substitution with iodoarenes on the terminal alkynyl carbon in (2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-propargylpyrazine. Bridged structures were formed from diiodoarenes. Homocoupling with bridge formation between two alkynyl units was effected by the same catalyst system with air as the oxidant. Mild hydrolysis gave the corresponding unsaturated amino acids and esters. The dicoupled amino acids have two triple bonds in conjugation in the bridge between the alpha,alpha'-carbons in the two glycine units.

  DOI：

  10.3891/acta.chem.scand.51-0873
• 作为产物：
  描述：

  (S)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 正丁基锂 、 air 、 二乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 29.0h， 生成 1,6-bis-((2S,5R)-2,5-dihydro-2-isopropyl-3,6-dimethoxy-5-pyrazinyl)hexa-2,4-diyne
  参考文献：
  名称：

  Stereoselective Synthesis of Alkynylglycines and alpha,alpha'-Alkynyl-Bridged Bis(glycines).

  摘要：

  Pd-CuI catalysis has been used to effect carbo-substitution with iodoarenes on the terminal alkynyl carbon in (2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-propargylpyrazine. Bridged structures were formed from diiodoarenes. Homocoupling with bridge formation between two alkynyl units was effected by the same catalyst system with air as the oxidant. Mild hydrolysis gave the corresponding unsaturated amino acids and esters. The dicoupled amino acids have two triple bonds in conjugation in the bridge between the alpha,alpha'-carbons in the two glycine units.

  DOI：

  10.3891/acta.chem.scand.51-0873

文献信息

• Stereoselective Synthesis of Alkynylglycines and alpha,alpha'-Alkynyl-Bridged Bis(glycines).
  作者：Synne Rødbotten、Tore Benneche、Kjell Undheim、Antonin Lycka、Jose Maria Moreno、Antonio Romerosa、Ward T. Robinson、Björn O. Roos、Claire Vallance、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0873

  日期：——

  Pd-CuI catalysis has been used to effect carbo-substitution with iodoarenes on the terminal alkynyl carbon in (2S,5R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-propargylpyrazine. Bridged structures were formed from diiodoarenes. Homocoupling with bridge formation between two alkynyl units was effected by the same catalyst system with air as the oxidant. Mild hydrolysis gave the corresponding unsaturated amino acids and esters. The dicoupled amino acids have two triple bonds in conjugation in the bridge between the alpha,alpha'-carbons in the two glycine units.