2-hydroxy-3-oxa-trans-decalin | 74924-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-hydroxy-3-oxa-trans-decalin
• 英文别名: 2-hydroxy-3-oxo-trans-decalin；(4aR,8aS)-3,4,4a,5,6,7,8,8a-octahydro-1H-isochromen-3-ol
• CAS: 74924-97-3；74924-98-4；131647-22-8
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: MTGDEEVVULEXSH-ZAZKALAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-oxa-trans-decalin 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以61%的产率得到trans-4a,5,6,7,8,8a-hexahydro-1H-isochromene
  参考文献：
  名称：

  Hydrolysis of α- and β-Glycosides. New Experimental Data and Modeling of Reaction Pathways

  摘要：

  The cyclization of oxocarbenium ion conformers 6alpha and 6beta (from 11E and 11Z) gave only the beta-glycoside 1beta, and the addition of methanol to the oxocarbenium ion 3 yielded mainly the alpha-glycoside 1alpha with both experiments being carried out under kinetically controlled conditions. RHF/6.31G* calculations reproduce well these experimental results and show that the endocyclic and the exocyclic C-O bond cleavage processes can compete in the hydrolysis of 1beta, whereas 1alpha gets hydrolyzed by exocyclic C-O bond cleavage only.

  DOI：

  10.1021/ol036220+
• 作为产物：
  描述：

  (3R,4aR,8aS)-3-methoxy-3,4,4a,5,6,7,8,8a-octahydro-1H-isochromene 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 2-hydroxy-3-oxa-trans-decalin
  参考文献：
  名称：

  Models for glycoside hydrolysis. Synthesis and hydrolytic studies of the anomers of a conformationally rigid acetal

  摘要：

  DOI：

  10.1021/jo01311a018

文献信息

• Models for glycoside hydrolysis. Synthesis and hydrolytic studies of the anomers of a conformationally rigid acetal
  作者：Paul Van Eikeren

  DOI：10.1021/jo01311a018

  日期：1980.11
• Hydrolysis of α- and β-Glycosides. New Experimental Data and Modeling of Reaction Pathways
  作者：Pierre Deslongchamps、Shigui Li、Yves L. Dory

  DOI：10.1021/ol036220+

  日期：2004.2.1

  The cyclization of oxocarbenium ion conformers 6alpha and 6beta (from 11E and 11Z) gave only the beta-glycoside 1beta, and the addition of methanol to the oxocarbenium ion 3 yielded mainly the alpha-glycoside 1alpha with both experiments being carried out under kinetically controlled conditions. RHF/6.31G* calculations reproduce well these experimental results and show that the endocyclic and the exocyclic C-O bond cleavage processes can compete in the hydrolysis of 1beta, whereas 1alpha gets hydrolyzed by exocyclic C-O bond cleavage only.