(+/-)-acetic acid 2-vinyl-[1,3]dioxolan-4-yl ester | 1360877-58-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-acetic acid 2-vinyl-[1,3]dioxolan-4-yl ester
• CAS: 1360877-58-2
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: FTCSGMXVLPQLFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+/-)-acetic acid 2-vinyl-[1,3]dioxolan-4-yl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 硫酸氢铵 、 palladium 10% on activated carbon 、 六甲基二硅氮烷 、 环己烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 rac-diethyl (2-((2R,4R)-4-(6-chloropurin-9-yl)-1,3-dioxolan-2-yl)ethyl)phosphonate
  参考文献：
  名称：

  Design and Synthesis of Novel 1′,3′-Dioxolane 5′-Deoxyphosphonic Acid Purine Analogues as Potent Antiviral Agents

  摘要：

  Electronic parameters of 1',3'-oxygen play significant roles in steering the conformation of nucleoside phosphonic acid analogues. To investigate the relationship of two oxygen atoms with antiviral enhancement, novel. 1',3'-dioxolane 5'-deoxyphosphonic acid purine analogues were synthesized via de novo acyclic stereoselective route from acrolein and glycolic acid. The synthesized nucleoside phosphonic acid analogues 19 and 19 were subjected to antiviral screening against several viruses, such. as HIV-1, HSV-1, HSV-2, and HCMV The guanine analogue 19 exhibits in vitro anti-HIV-1 activity similar to that of 9[2-(phosphonomethoxy)ethyl]adenine (PMEA) in MT-4 cells.

  DOI：

  10.1080/15257770.2011.643849
• 作为产物：
  描述：

  2-vinyl-1,3-dioxolan-4-one 在 吡啶 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成 (+/-)-acetic acid 2-vinyl-[1,3]dioxolan-4-yl ester
  参考文献：
  名称：

  Design and Synthesis of Novel 1′,3′-Dioxolane 5′-Deoxyphosphonic Acid Purine Analogues as Potent Antiviral Agents

  摘要：

  Electronic parameters of 1',3'-oxygen play significant roles in steering the conformation of nucleoside phosphonic acid analogues. To investigate the relationship of two oxygen atoms with antiviral enhancement, novel. 1',3'-dioxolane 5'-deoxyphosphonic acid purine analogues were synthesized via de novo acyclic stereoselective route from acrolein and glycolic acid. The synthesized nucleoside phosphonic acid analogues 19 and 19 were subjected to antiviral screening against several viruses, such. as HIV-1, HSV-1, HSV-2, and HCMV The guanine analogue 19 exhibits in vitro anti-HIV-1 activity similar to that of 9[2-(phosphonomethoxy)ethyl]adenine (PMEA) in MT-4 cells.

  DOI：

  10.1080/15257770.2011.643849