2-[(5-Methyl-2-phenylmethoxyphenyl)methyl]oxirane | 863291-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(5-Methyl-2-phenylmethoxyphenyl)methyl]oxirane
• 英文别名: 2-[(5-methyl-2-phenylmethoxyphenyl)methyl]oxirane
• CAS: 863291-69-4
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: JRUPMITUSACVHF-UHFFFAOYSA-N

物化性质

• 沸点：
  382.3±27.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(5-Methyl-2-phenylmethoxyphenyl)methyl]oxirane 在 palladium on activated charcoal 、 三乙胺 氢气 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (+/-)-5-methyl-2-hydroxymethyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  A new synthetic approach to enantiomerically enriched dihydrobenzofurans: use of a hydrolytic kinetic resolution and an intramolecular epoxide ring opening protocol using 1-benzyloxy-2-oxiranylmethylbenzenes

  摘要：

  A novel approach towards the preparation of racemic 1-benzyloxy-2-oxiranylmethylbenzenes using dimethyldioxirane and their hydrolytic kinetic resolution using (R,R)(Salen)Co(III)(OAc) (Jacobsen's catalyst) to afford the (R)-epoxides and (S)1,2-diols. enantioselectively, is described. The (R)-1-benzyloxy-2-oxiranylmethylbenzenes were then cyclized via an intramolecular epoxide opening reaction to give (S)-2-hydroxymethyl-2,3-dihydrobenzofurans. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.04.120
• 作为产物：
  描述：

  2-烯丙基-4-甲基苯酚 在 edetate disodium 、 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 13.3h， 生成 2-[(5-Methyl-2-phenylmethoxyphenyl)methyl]oxirane
  参考文献：
  名称：

  A new synthetic approach to enantiomerically enriched dihydrobenzofurans: use of a hydrolytic kinetic resolution and an intramolecular epoxide ring opening protocol using 1-benzyloxy-2-oxiranylmethylbenzenes

  摘要：

  A novel approach towards the preparation of racemic 1-benzyloxy-2-oxiranylmethylbenzenes using dimethyldioxirane and their hydrolytic kinetic resolution using (R,R)(Salen)Co(III)(OAc) (Jacobsen's catalyst) to afford the (R)-epoxides and (S)1,2-diols. enantioselectively, is described. The (R)-1-benzyloxy-2-oxiranylmethylbenzenes were then cyclized via an intramolecular epoxide opening reaction to give (S)-2-hydroxymethyl-2,3-dihydrobenzofurans. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.04.120

文献信息

• A new synthetic approach to enantiomerically enriched dihydrobenzofurans: use of a hydrolytic kinetic resolution and an intramolecular epoxide ring opening protocol using 1-benzyloxy-2-oxiranylmethylbenzenes
  作者：Umadevi Bhoga

  DOI：10.1016/j.tetlet.2005.04.120

  日期：2005.8

  A novel approach towards the preparation of racemic 1-benzyloxy-2-oxiranylmethylbenzenes using dimethyldioxirane and their hydrolytic kinetic resolution using (R,R)(Salen)Co(III)(OAc) (Jacobsen's catalyst) to afford the (R)-epoxides and (S)1,2-diols. enantioselectively, is described. The (R)-1-benzyloxy-2-oxiranylmethylbenzenes were then cyclized via an intramolecular epoxide opening reaction to give (S)-2-hydroxymethyl-2,3-dihydrobenzofurans. (c) 2005 Published by Elsevier Ltd.