(3R,4aR,8aS)-3-methoxy-3,4,4a,5,6,7,8,8a-octahydro-1H-isochromene | 74925-00-1

• 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: (3R,4aR,8aS)-3-methoxy-3,4,4a,5,6,7,8,8a-octahydro-1H-isochromene
• CAS: 74925-00-1
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: WRAJQRLRZVNTKE-OPRDCNLKSA-N

物化性质

• 沸点：
  228.2±8.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• 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：

  (3R,4aR,8aS)-3-methoxy-3,4,4a,5,6,7,8,8a-octahydro-1H-isochromene 在 甲醇 、 Dowex-50-X (H⁺ form) 作用下， 生成 2-oxa-3α-methoxy-cis-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
• 作为产物：
  描述：

  在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 、 氘代乙腈 为溶剂， 反应 0.67h， 生成 (3R,4aR,8aS)-3-methoxy-3,4,4a,5,6,7,8,8a-octahydro-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+

文献信息

• Experimental evidence for a synperiplanar stereoelectronic effect in the ozonolysis of a tricyclic acetal
  作者：Shigui Li、Pierre Deslongchamps

  DOI：10.1016/s0040-4039(00)61559-9

  日期：1993.11

  Tricyclic acetal 1 in which the ring oxygen has one electron pair synperiplanar to the CH bond is easily oxidized with ozone.

  三环缩醛1中的环氧具有一个相对于CH键在平面上的电子对，很容易被臭氧氧化。
• 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.