2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl)-methyl]thiophene | 194161-45-0

• 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: 2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl)-methyl]thiophene
• CAS: 194161-45-0
• 化学式: C₂₄H₃₆N₄O₄S
• 分子量: 476.64
• InChiKey: UPXGUFLIKRAGFR-RAUXBKROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• 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：
  9.0

反应信息

• 作为反应物：
  描述：

  2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl)-methyl]thiophene 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 (S)-2-Amino-3-[3-((S)-2-amino-2-methoxycarbonyl-ethyl)-thiophen-2-yl]-propionic acid methyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Thiophenedimethyl- and Benzenedimethyl- alpha,alpha'-Bridged Bis(glycines).

  摘要：

  Conformationally constrained cystine analogues have been synthesized which have an all-carbon backbone-chain as a bridge between the alpha,alpha'-positions in two glycine units. An aromatic ring consisting of a 1,2-disubstituted benzene or a 2,3- and 2,5-disubstituted thiophene has been inserted into the bridge. Chiral auxiliaries were used to effect stereoselective syntheses of the (S,S)-bis(amino acids). The latter were further derivatized as Fmoc-derivatives suitable for peptide syntheses. The product 2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy- 2-isopropyl-5-pyrazinyl)methyl]-5-methylthiophene has been subjected to X-ray analysis.

  DOI：

  10.3891/acta.chem.scand.51-0392
• 作为产物：
  描述：

  2-噻吩甲酸 在 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 8.67h， 生成 2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl)-methyl]thiophene
  参考文献：
  名称：

  Stereoselective Synthesis of Thiophenedimethyl- and Benzenedimethyl- alpha,alpha'-Bridged Bis(glycines).

  摘要：

  Conformationally constrained cystine analogues have been synthesized which have an all-carbon backbone-chain as a bridge between the alpha,alpha'-positions in two glycine units. An aromatic ring consisting of a 1,2-disubstituted benzene or a 2,3- and 2,5-disubstituted thiophene has been inserted into the bridge. Chiral auxiliaries were used to effect stereoselective syntheses of the (S,S)-bis(amino acids). The latter were further derivatized as Fmoc-derivatives suitable for peptide syntheses. The product 2,3-bis[(2R,5S)-(2,5-dihydro-3,6-dimethoxy- 2-isopropyl-5-pyrazinyl)methyl]-5-methylthiophene has been subjected to X-ray analysis.

  DOI：

  10.3891/acta.chem.scand.51-0392