cis-4,6-Dibutyl-1,3-dioxan | 13309-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: cis-4,6-Dibutyl-1,3-dioxan
• 英文别名: (4R,6S)-4,6-dibutyl-1,3-dioxane
• CAS: 13309-83-6
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: UCPAZYFDPOUDHP-TXEJJXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  6
• 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

• 作为产物：
  描述：

  聚合甲醛 、 十一烷-5,7-二酮 在 sodium tetrahydroborate 、 oxonium 作用下， 生成 cis-4,6-Dibutyl-1,3-dioxan 、 d,l-4,6-di-n-butyl-1,3-dioxane
  参考文献：
  名称：

  Fragmentation of the protonated stereoisomers of 5,7-Undecanediol and its bis(trimethylsilyl) ether under conditions of isobutane chemical ionization

  摘要：

  AbstractThe chemical ionization induced fragmentation behaviour of an open chain model compound, 5,7‐undecanediol (meso and d,l stereoisomers), is studied and compared with that of previously studied alicyclic models, e.g. cyclohexanediols (cis and trans isomers). In close analogy to the latter, the major fragmentation processes are the one‐ and twofold loss of H2O from the protonated molecules [MH]+. As borne out by appropriately deuterium labelled analogues, the first loss of H2O is invariably a ‘clean’ heterolysis. The second loss is considerably more complex in that 1,3‐ and 1,4‐elimination processes occur concurrently. While the 1,4‐mode may be a direct elimination process in both types of compounds, the 1,3‐mode is rearrangement induced in both. Whereas skeletal rearrangement (ring contraction) precedes this 1,3‐elimination in the alicyclic models, hydrogen rearrangement (1,2‐hydride shift) precedes it in the open chain model. No pronounced stereochemical effect is observed on the mechanistic course of the elimination processes, but is observed in their relative ease. The trimethylsilyl ethers of the stereoisomers of 5,7‐undecanediol are also studied for analogous reactions, and are discussed in this context.

  DOI：

  10.1002/oms.1210160111

文献信息

• Fragmentation of the protonated stereoisomers of 5,7-Undecanediol and its bis(trimethylsilyl) ether under conditions of isobutane chemical ionization
  作者：Roland Wolfschütz、Helmut Schwarz、Wolfgang Blum、Wilhelm J. Richter

  DOI：10.1002/oms.1210160111

  日期：1981.1

  AbstractThe chemical ionization induced fragmentation behaviour of an open chain model compound, 5,7‐undecanediol (meso and d,l stereoisomers), is studied and compared with that of previously studied alicyclic models, e.g. cyclohexanediols (cis and trans isomers). In close analogy to the latter, the major fragmentation processes are the one‐ and twofold loss of H2O from the protonated molecules [MH]+. As borne out by appropriately deuterium labelled analogues, the first loss of H2O is invariably a ‘clean’ heterolysis. The second loss is considerably more complex in that 1,3‐ and 1,4‐elimination processes occur concurrently. While the 1,4‐mode may be a direct elimination process in both types of compounds, the 1,3‐mode is rearrangement induced in both. Whereas skeletal rearrangement (ring contraction) precedes this 1,3‐elimination in the alicyclic models, hydrogen rearrangement (1,2‐hydride shift) precedes it in the open chain model. No pronounced stereochemical effect is observed on the mechanistic course of the elimination processes, but is observed in their relative ease. The trimethylsilyl ethers of the stereoisomers of 5,7‐undecanediol are also studied for analogous reactions, and are discussed in this context.