O-isopropyl-S-propargyl xanthate | 22118-16-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: O-isopropyl-S-propargyl xanthate
• 英文别名: Prop-2-inyl-xanthogensaeure-isopropylester；O-propan-2-yl prop-2-ynylsulfanylmethanethioate
• CAS: 22118-16-7
• 化学式: C₇H₁₀OS₂
• 分子量: 174.288
• InChiKey: INCLOPAMXCOUOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (RS)-2-(N,N-di-tert-butoxycarbonylamino)-3-[3-isopropoxy-5(1H-5-tetrazolyl)-4-isoxazolyl]propionate 、 O-isopropyl-S-propargyl xanthate 以 甲苯 为溶剂， 反应 16.0h， 以60%的产率得到tert-butyl (RS)-2-(tert-butoxycarbonylamino)-3-[3-isopropoxy-5(2-isopropyl-2H-5-tetrazolyl)-4-isoxazolyl]propionate
  参考文献：
  名称：

  Convergent Synthesis and Pharmacology of Substituted Tetrazolyl-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid Analogues

  摘要：

  The synthesis and pharmacological characterization of 1- and 2-alkyltetrazolyl analogues of (RS)-2-amino-3-[3-hydroxy-5-(2-methyl-2H-5-tetrazolyl)-4-isoxazolyl]propionic acid (2-Me-Tet-AMPA), a highly potent and selective agonist at AMPA receptors, are presented. A shorter and more convergent synthetic route than previously described, employing a new method for introducing the amino acid moiety, was developed for these derivatives. The 2-substituted isomers were selective agonists, and their activity correlated inversely with the size of the substituent. Structural explanations of the structure-activity relationship are provided.

  DOI：

  10.1021/jm050014l
• 作为产物：
  描述：

  potassium isopropylxanthate 、 3-溴丙炔 以 乙醇 为溶剂， 生成 O-isopropyl-S-propargyl xanthate
  参考文献：
  名称：

  Aliev,M.I. et al., Journal of general chemistry of the USSR, 1968, vol. 38, p. 2537 - 2538

  摘要：

  DOI：

文献信息

• Aliev,M.I. et al., Journal of general chemistry of the USSR, 1968, vol. 38, p. 2537 - 2538
  作者：Aliev,M.I. et al.

  DOI：——

  日期：——
• Convergent Synthesis and Pharmacology of Substituted Tetrazolyl-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid Analogues
  作者：Stine B. Vogensen、Rasmus P. Clausen、Jeremy R. Greenwood、Tommy N. Johansen、Darryl S. Pickering、Birgitte Nielsen、Bjarke Ebert、Povl Krogsgaard-Larsen

  DOI：10.1021/jm050014l

  日期：2005.5.1

  The synthesis and pharmacological characterization of 1- and 2-alkyltetrazolyl analogues of (RS)-2-amino-3-[3-hydroxy-5-(2-methyl-2H-5-tetrazolyl)-4-isoxazolyl]propionic acid (2-Me-Tet-AMPA), a highly potent and selective agonist at AMPA receptors, are presented. A shorter and more convergent synthetic route than previously described, employing a new method for introducing the amino acid moiety, was developed for these derivatives. The 2-substituted isomers were selective agonists, and their activity correlated inversely with the size of the substituent. Structural explanations of the structure-activity relationship are provided.