2-vinyl-1,3-dioxolan-4-one | 145437-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-vinyl-1,3-dioxolan-4-one
• 英文别名: 2-ethenyl-1,3-dioxolan-4-one
• CAS: 145437-79-2
• 化学式: C₅H₆O₃
• 分子量: 114.101
• InChiKey: HPGSTQUYCLPWMH-UHFFFAOYSA-N

物化性质

• 沸点：
  175.3±28.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  羟基乙酸 、 丙烯醛 以 苯 为溶剂， 以59%的产率得到2-vinyl-1,3-dioxolan-4-one
  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

文献信息

• A Radical Route to α-Substituted Enones
  作者：Bartosz Bieszczad、Samir Z. Zard

  DOI：10.1021/acs.orglett.2c02783

  日期：2022.9.30

  A versatile strategy for the α-substitution of enones through the formal fusion between enones and unactivated alkenes is described. It relies on the formation and use of α-xanthyl-β-hydroxy ketones, which can be considered as synthetic equivalents of the high energy and difficult to tame alkenyl radicals. The process, which can often be accomplished one-pot, could be extended in one case to an α,β-unsaturated

  描述了通过烯酮和未活化烯烃之间的正式融合来进行烯酮α-取代的通用策略。它依赖于 α-xanthyl-β-羟基酮的形成和使用，它可以被认为是高能且难以驯服的烯基自由基的合成等价物。该过程通常可以一锅完成，在一种情况下可以扩展到α,β-不饱和酯。