2-(1,2-dibromoethyl)-2-bromomethyl-1,3-dioxolane | 1178975-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1,2-dibromoethyl)-2-bromomethyl-1,3-dioxolane
• 英文别名: 2-(Bromomethyl)-2-(1,2-dibromoethyl)-1,3-dioxolane
• CAS: 1178975-55-7
• 化学式: C₆H₉Br₃O₂
• 分子量: 352.848
• InChiKey: RZIZNSCIEAOZBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-(1,2-dibromoethyl)-2-bromomethyl-1,3-dioxolane 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到2-bromomethyl-2-ethynyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of 1-Bromo-3-butyn-2-one and 1,3-Dibromo-3-buten-2-one

  摘要：

  Synthetic procedures for the preparation of 1-bromo-3-butyn-2-one and 1,3-dibromo-3-buten-2-one are given. These compounds are prepared from 2-bromomethyl-2-vinyl-1,3-dioxolane, which can readily be prepared from 2-ethyl- 2-methyl-1,3-dioxolane. The synthetic routes are as follows: 2-bromomethyl-2-vinyl-1,3-dioxolane is converted to 2-(1,2-dibromoethyl)-2-bromomethyl-1,3-dioxolane. Double dehydrobromination with tBuOK affords 2-ethynyl-2-bromomethyl-1,3-dioxolane. Formolysis with formic acid gives 1-bromo-3-butyn-2-one. Deacetalized 2-bromoethyl-2-vinyl-1,3-dioxolane was treated with Br2 and Li2CO3/12-crown-4 in tetrahydrofuran to give 1,3-dibrom-3-buten-2-one in moderate yield.

  DOI：

  10.1080/00397910802654872
• 作为产物：
  描述：

  2-bromomethyl-2-vinyl-1,3-dioxolane 在 溴 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到2-(1,2-dibromoethyl)-2-bromomethyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of 1-Bromo-3-butyn-2-one and 1,3-Dibromo-3-buten-2-one

  摘要：

  Synthetic procedures for the preparation of 1-bromo-3-butyn-2-one and 1,3-dibromo-3-buten-2-one are given. These compounds are prepared from 2-bromomethyl-2-vinyl-1,3-dioxolane, which can readily be prepared from 2-ethyl- 2-methyl-1,3-dioxolane. The synthetic routes are as follows: 2-bromomethyl-2-vinyl-1,3-dioxolane is converted to 2-(1,2-dibromoethyl)-2-bromomethyl-1,3-dioxolane. Double dehydrobromination with tBuOK affords 2-ethynyl-2-bromomethyl-1,3-dioxolane. Formolysis with formic acid gives 1-bromo-3-butyn-2-one. Deacetalized 2-bromoethyl-2-vinyl-1,3-dioxolane was treated with Br2 and Li2CO3/12-crown-4 in tetrahydrofuran to give 1,3-dibrom-3-buten-2-one in moderate yield.

  DOI：

  10.1080/00397910802654872

文献信息

• Synthesis of 1-Bromo-3-butyn-2-one and 1,3-Dibromo-3-buten-2-one
  作者：Alemayehu Mekonnen、Andreas Westerlund、Martina Havelkova、Alexandre Descomps、Rolf Carlson

  DOI：10.1080/00397910802654872

  日期：2009.6.23

  Synthetic procedures for the preparation of 1-bromo-3-butyn-2-one and 1,3-dibromo-3-buten-2-one are given. These compounds are prepared from 2-bromomethyl-2-vinyl-1,3-dioxolane, which can readily be prepared from 2-ethyl- 2-methyl-1,3-dioxolane. The synthetic routes are as follows: 2-bromomethyl-2-vinyl-1,3-dioxolane is converted to 2-(1,2-dibromoethyl)-2-bromomethyl-1,3-dioxolane. Double dehydrobromination with tBuOK affords 2-ethynyl-2-bromomethyl-1,3-dioxolane. Formolysis with formic acid gives 1-bromo-3-butyn-2-one. Deacetalized 2-bromoethyl-2-vinyl-1,3-dioxolane was treated with Br2 and Li2CO3/12-crown-4 in tetrahydrofuran to give 1,3-dibrom-3-buten-2-one in moderate yield.