4-methylene-1,3-dioxolane | 4362-24-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 4-methylene-1,3-dioxolane
• 英文别名: 4-methylidene-1,3-dioxolane
• CAS: 4362-24-7
• 化学式: C₄H₆O₂
• 分子量: 86.0904
• InChiKey: UMEHTUCYIDSLRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methylene-1,3-dioxolane 在 Lewatit CNP 80 作用下， 以55%的产率得到1,3-二噁唑,4-甲基-
  参考文献：
  名称：

  Synthese von substituierten 1,3-Dioxolen

  摘要：

  DOI：

  10.1055/s-1983-30283
• 作为产物：
  描述：

  4-chloromethyl-[1,3]dioxolane 在 氢氧化钾 作用下， 生成 4-methylene-1,3-dioxolane
  参考文献：
  名称：

  Resinous polymer of methylene dioxolane

  摘要：

  公开号：

  US02382640A1

文献信息

• Novel Dioxolane And Dioxane Derivatives And A Process For Their Preparation
  申请人：PAZENOK Sergii

  公开号：US20110152531A1

  公开（公告）日：2011-06-23

  The present invention relates to novel acylmethylene-1,3-dioxolanes and acylmethylene-1,4-dioxanes of the general formula (I) in which R 1 , R 2 , R 3 and n have the meanings given in the description, and also a novel process for their preparation. Acylmethylene-1,3-dioxolanes and acylmethylene-1,4-dioxanes are important intermediates for the preparation of pyrazoles and anthranilamides, which can be used as insecticides.

  本发明涉及一种新型的通式（I）中的酰亚甲基-1,3-二氧杂环戊烷和酰亚甲基-1,4-二氧杂环烷，其中R1、R2、R3和n的含义如描述中所述，并且涉及它们的制备新方法。酰亚甲基-1,3-二氧杂环戊烷和酰亚甲基-1,4-二氧杂环烷是制备吡唑和蒽酰胺的重要中间体，可用作杀虫剂。
• Synthesis of Fluorine‐Containing 3‐Aminocyclopent‐2‐enones via Intramolecular Cyclization
  作者：Elena N. Shaitanova、Igor I. Gerus、Olga A. Balabon、Viktor E. Ivasyshyn、Karen V. Tarasenko、Constantin G. Daniliuc、Günter Haufe

  DOI：10.1002/ejoc.202001218

  日期：2020.12.13

  An optimized protocol for the preparation of fluorine‐containing acyclic enones, which react with secondary amines to form fluorinated 3‐amino‐cyclopent‐2‐enones via 4‐amino‐2,3‐dihydrofuran‐2‐ols was developed. A plausible mechanism is proposed.

  开发了一种优化的制备含氟无环烯酮的方案，该环烯酮与仲胺反应，通过4-氨基-2,3-二氢呋喃-2-醇形成氟化的3-氨基环戊-2-烯酮。提出了一种合理的机制。
• Orth, Angewandte Chemie, 1952, vol. 64, p. 544,547
  作者：Orth

  DOI：——

  日期：——
• Fischer et al., Chemische Berichte, 1930, vol. 63, p. 1732,1740
  作者：Fischer et al.

  DOI：——

  日期：——
• Synthesis and Properties of Polyfunctional Cyclic β-Alkoxy-α,β-Unsaturated Ketones Based on 4-Methylene-1,3-dioxolanes
  作者：Igor I. Gerus、Olga A. Balabon、Sergiy V. Pazenok、Norbert Lui、Ivan S. Kondratov、Karen V. Tarasenko、Elena N. Shaitanova、Viktor E. Ivasyshyn、Valery P. Kukhar

  DOI：10.1002/ejoc.201800786

  日期：2018.8.1

  New CCl3‐ and CF3‐substituted enones, bearing additional hidden hydroxymethyl functions, were prepared by acylation of 4‐methylene 1,3‐dioxolanes. The synthesized enones are interesting building blocks for agrochemical and medicinal chemistry research. The reactivity of synthesized enones with various amines was studied, and enaminones 13 and 14 were obtained under NH3 interaction; the reaction with aliphatic primary amines afforded enaminones 17 in high yields as equilibrium mixtures of E and Z isomers. The reaction of fluorinated enone 9c with anilines afforded a mixture of products, including non‐aromatic heterocyclic compounds 25 and 26 bearing the CF3 group as well as furan 27 with CF3 and amino functions at positions 5 and 3, respectively. The hydrolysis of enone 9c afforded cyclic compound 11.

表征谱图