3,4-dihydro-2H,6H-3,6-epoxy-benzo[1,5]dioxocine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dihydro-2H,6H-3,6-epoxy-benzo[1,5]dioxocine
• 英文别名: 3,4-dihydro-2H,6H-3,6-epoxybenzo[1,5]dioxocine；3,4-Dihydro-2H,6H-3,6-epoxido-benzo[b][1,5]dioxocin；3,4-dihydro-2H,6H-3,6-epoxy-1,5-benzodioxocine；8,12,13-trioxatricyclo[8.2.1.02,7]trideca-2,4,6-triene
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: KJISXZFEENNRJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(oxiran-2-ylmethoxy)benzaldehyde 在 苄基三乙基氯化铵 作用下， 以 环氧氯丙烷 为溶剂， 以1.08 g的产率得到3,4-dihydro-2H,6H-3,6-epoxy-benzo[1,5]dioxocine
  参考文献：
  名称：

  Study of the interaction of salicyl aldehydes with epichlorohydrin: a simple, convenient, and efficient method for the synthesis of 3,6-epoxy[1,5]dioxocines

  摘要：

  An efficient synthetic method for 3,6-epoxyl[1,5]dioxocines via the condensation of salicyl aldehydes and epichlorohydrin, using benzyl triethylammonium chloride as catalyst, is described. The use of neutral or electron-deficient salicyl aldehydes in all cases was found to give 3,6-epoxy[1,5]dioxocine derivatives in good yields. The structural features were resolved by IR, NMR spectroscopy, mass spectrometry, and ultimately proved by X-ray crystallographic analysis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.093

文献信息

• Muscle-Relaxing Compounds Similar to 3-(o-Toloxy)-1,2-propanediol. II. Substituted Alkanediols¹
  作者：Harry L. Yale、Edward J. Pribyl、William Braker、Jack Bernstein、W. A. Lott

  DOI：10.1021/ja01164a108

  日期：1950.8
• The condensation of epichlorohydrin with monohydric phenols and with catechol
  作者：O. Stephenson

  DOI：10.1039/jr9540001571

  日期：——
• Synthesis of 3,6-epoxy[1,5]dioxocines from 2-hydroxyaromatic benzaldehydes
  作者：Koneni V. Sashidhara、Abdhesh Kumar、K. Bhaskara Rao

  DOI：10.1016/j.tetlet.2011.08.095

  日期：2011.10

  Convenient and facile one step synthesis of medicinally relevant new 3,6-epoxy[1,5]dioxocines from 2-hydroxyaromatic benzaldehydes is described. The scope of the method was validated by examining the use of both electron rich and electron-deficient 2-hydroxyaromatic benzaldehydes. (C) 2011 Elsevier Ltd. All rights reserved.
• Study of the interaction of salicyl aldehydes with epichlorohydrin: a simple, convenient, and efficient method for the synthesis of 3,6-epoxy[1,5]dioxocines
  作者：Dainius Janeliunas、Maryte Daskeviciene、Tadas Malinauskas、Vytautas Getautis

  DOI：10.1016/j.tet.2009.07.093

  日期：2009.10

  An efficient synthetic method for 3,6-epoxyl[1,5]dioxocines via the condensation of salicyl aldehydes and epichlorohydrin, using benzyl triethylammonium chloride as catalyst, is described. The use of neutral or electron-deficient salicyl aldehydes in all cases was found to give 3,6-epoxy[1,5]dioxocine derivatives in good yields. The structural features were resolved by IR, NMR spectroscopy, mass spectrometry, and ultimately proved by X-ray crystallographic analysis. (C) 2009 Elsevier Ltd. All rights reserved.