4-(1-adamantyl)-3,6-dihydro-1,2-dioxine | 681855-84-5

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 4-(1-adamantyl)-3,6-dihydro-1,2-dioxine
• 英文别名: 4-(1-adamantyl)-3,6-dihydro-1,2-dioxin
• CAS: 681855-84-5
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: SVUMJYGVLHXSRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 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-(1-adamantyl)-3,6-dihydro-1,2-dioxine 在 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 5.0h， 生成 1a-(1-adamantyl)tetrahydrooxireno[2,3-c]furan
  参考文献：
  名称：

  Triphenylphosphine-Induced Ring Contraction of 1,2-Dioxines

  摘要：

  Triphenylphosphine inserts into the peroxide bond of 1,2-dioxines, initiating ring contraction with loss of triphenylphosphine oxide. This process yields dihydrofuran oxides in 54-97% yield from oxirenyl[2,3-c] [1,2]dioxines and dihydrofurans from 3,6-dihydro-1,2-dioxines with inversion of stereochemistry at either the 2 or 5 position in the furan product.

  DOI：

  10.1021/jo030330c
• 作为产物：
  描述：

  2-(1-adamantyl)-1,3-butadiene 在 氧气 、 Rose Bengal bis(triethylammonium) salt 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以91%的产率得到4-(1-adamantyl)-3,6-dihydro-1,2-dioxine
  参考文献：
  名称：

  Dihydroxylation of 4-Substituted 1,2-Dioxines: A Concise Route to Branched Erythro Sugars

  摘要：

  The synthesis of 2-C-branched erythritol derivatives, including the plant sugar (+/-)-2-C-methylerythritol 2, was achieved through a dihydroxylation/reduction sequence on a series of 4-substituted 1,2-dioxines 3. The asymmetric dihydroxylation of 1,2-dioxines was examined, providing access to optically enriched dihydroxy 1,2-dioxanes 4. The synthesized 1,2-dioxanes were converted to other erythro sugar analogues and tetrahydrofurans through controlled cleavage of the endoperoxide linkage.

  DOI：

  10.1021/jo900669u

文献信息

• Triphenylphosphine-Induced Ring Contraction of 1,2-Dioxines
  作者：Ben W. Greatrex、Dennis K. Taylor

  DOI：10.1021/jo030330c

  日期：2004.4.1

  Triphenylphosphine inserts into the peroxide bond of 1,2-dioxines, initiating ring contraction with loss of triphenylphosphine oxide. This process yields dihydrofuran oxides in 54-97% yield from oxirenyl[2,3-c] [1,2]dioxines and dihydrofurans from 3,6-dihydro-1,2-dioxines with inversion of stereochemistry at either the 2 or 5 position in the furan product.
• Dihydroxylation of 4-Substituted 1,2-Dioxines: A Concise Route to Branched Erythro Sugars
  作者：Tony V. Robinson、Daniel Sejer Pedersen、Dennis K. Taylor、Edward R. T. Tiekink

  DOI：10.1021/jo900669u

  日期：2009.7.17

  The synthesis of 2-C-branched erythritol derivatives, including the plant sugar (+/-)-2-C-methylerythritol 2, was achieved through a dihydroxylation/reduction sequence on a series of 4-substituted 1,2-dioxines 3. The asymmetric dihydroxylation of 1,2-dioxines was examined, providing access to optically enriched dihydroxy 1,2-dioxanes 4. The synthesized 1,2-dioxanes were converted to other erythro sugar analogues and tetrahydrofurans through controlled cleavage of the endoperoxide linkage.