(3aS,7aS)-2-Methoxymethyl-octahydro-benzofuran | 128023-42-7

• 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: (3aS,7aS)-2-Methoxymethyl-octahydro-benzofuran
• CAS: 128023-42-7
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: MKCGNFWPVQWUDU-SMILAEQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  甲醇 、 cis-2-allylcyclohexanol 在 萘-1,4-二腈 、 二苯基二硒醚 作用下， 反应 32.0h， 以72%的产率得到(3aS,7aS)-2-Methoxymethyl-octahydro-benzofuran
  参考文献：
  名称：

  Photoinduced Electron Transfer Initiated Activation of Organoselenium Substrates as Carbocation Equivalents: Sequential One-Pot Selenylation and Deselenylation Reaction

  摘要：

  The investigation presented in this paper explores the mechanistic aspects and synthetic potentials of PET activation of organoselenium substrates. Fluorescence quenching of (DCN)-D-1* by a number of organoselenium compounds (RCH(2)SeR', 1-4), correlation of the fluorescence quenching rate constants with the oxidation potentials of 1-4, and the dependence of photodissociation quantum yields of 1-4 on their concentration suggests the occurrence of electron transfer processes between (DCN)-D-1* and 1-4. Steady-state photolysis of 1-4 in the presence of (DCN)-D-1* leads to the efficient one-electron oxidative heterolytic dissociation of the carbon-selenium bond to produce the carbocation (RCH(2)(+) or equivalent) and radical-centered selenium species (R'Se-.) via the intermediacy of cation-radical [(RCH(2)SeR')(+.)]. Nucleophilic assistance in the fragmentation of (RCH(2)SeR')(+.) by methanol has been suggested on the basis of products obtained from the control PET reaction of neopentyl phenyl selenide (8). The synthetic utility of these findings has been demonstrated for the deselenylation (Table 4) as well as one-spot sequential selenylation-deselenylation (Table 5) reactions.

  DOI：

  10.1021/jo00103a031

文献信息

• Photoinduced single electron transfer initiated heterolytic carbon-selenium bond dissociation. Sequential one-pot selenenylation and deselenenylation reaction
  作者：Ganesh Pandey、B. B. V. Soma Sekhar、U. T. Bhalerao

  DOI：10.1021/ja00170a045

  日期：1990.7