(+/-)-1-(Hydroxymethyl)-3-methoxy-1-cyclopentene | 143546-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-1-(Hydroxymethyl)-3-methoxy-1-cyclopentene
• 英文别名: (3-Methoxycyclopenten-1-yl)methanol
• CAS: 143546-01-4
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: XBBDKHGOKBATQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (+/-)-1-(Hydroxymethyl)-3-methoxy-1-cyclopentene 在 咪唑 、 三氟甲磺酸三甲基硅酯 、 叠氮基三甲基硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (+/-)-3-Azido-1-<<(tert-butyldiphenylsilyl)oxy>methyl>cyclopent-1-ene
  参考文献：
  名称：

  An allylic azide route to 4'-azido carbocyclic nucleosides. Synthesis of (.+-.)-(1'.alpha.,2'.alpha.,3'.beta.)- and (.+-.)-(1'.alpha.,2'.beta.,3'.beta.)-1-[1-azido-2-hydroxy-1-(hydroxymethyl)-3-cyclopentyl]thymine

  摘要：

  Treatment of (+/-)-1-[[(tert-butyldiphenylsilyl)oxy]methyl]-3-methoxycyclopent-1-ene (17) with azidotrimethylsilane under Lewis acid catalyzed conditions gave an equilibrium mixture of allylic azides 18 and 19. Epoxidation of this mixture with peroxybenzimidic acid gave key epoxide (+/-)-(1alpha,2alpha,5alpha)-2-azido-2-[[tert-butyldiphenylsilyl)oxy]methyl]-6-oxabicyclo[3.1.0]hexane (5). Alternate routes designed to give tertiary azide precursors to 5 led to unanticipated products which are described. Title compound 28 was prepared by ring opening of 5 under Vorbruggen conditions followed by deprotection. Inversion of configuration at C-6' to give compound 30 was effected via O2,6'-cyclic intermediates 31 and 32. The relative stereochemistry of compounds in this series was suggested by NOE data for bromohydrins 23 and 26 and was confirmed by preparation of the fused oxetane 34.

  DOI：

  10.1021/jo00048a010
• 作为产物：
  描述：

  2-methoxy-hexanedial 在 sodium tetrahydroborate 、 dibenzylammonium trifluoroacetate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.17h， 生成 (+/-)-1-(Hydroxymethyl)-3-methoxy-1-cyclopentene
  参考文献：
  名称：

  An allylic azide route to 4'-azido carbocyclic nucleosides. Synthesis of (.+-.)-(1'.alpha.,2'.alpha.,3'.beta.)- and (.+-.)-(1'.alpha.,2'.beta.,3'.beta.)-1-[1-azido-2-hydroxy-1-(hydroxymethyl)-3-cyclopentyl]thymine

  摘要：

  Treatment of (+/-)-1-[[(tert-butyldiphenylsilyl)oxy]methyl]-3-methoxycyclopent-1-ene (17) with azidotrimethylsilane under Lewis acid catalyzed conditions gave an equilibrium mixture of allylic azides 18 and 19. Epoxidation of this mixture with peroxybenzimidic acid gave key epoxide (+/-)-(1alpha,2alpha,5alpha)-2-azido-2-[[tert-butyldiphenylsilyl)oxy]methyl]-6-oxabicyclo[3.1.0]hexane (5). Alternate routes designed to give tertiary azide precursors to 5 led to unanticipated products which are described. Title compound 28 was prepared by ring opening of 5 under Vorbruggen conditions followed by deprotection. Inversion of configuration at C-6' to give compound 30 was effected via O2,6'-cyclic intermediates 31 and 32. The relative stereochemistry of compounds in this series was suggested by NOE data for bromohydrins 23 and 26 and was confirmed by preparation of the fused oxetane 34.

  DOI：

  10.1021/jo00048a010

文献信息

• An allylic azide route to 4'-azido carbocyclic nucleosides. Synthesis of (.+-.)-(1'.alpha.,2'.alpha.,3'.beta.)- and (.+-.)-(1'.alpha.,2'.beta.,3'.beta.)-1-[1-azido-2-hydroxy-1-(hydroxymethyl)-3-cyclopentyl]thymine
  作者：Hans Maag、Robert M. Rydzewski

  DOI：10.1021/jo00048a010

  日期：1992.10

  Treatment of (+/-)-1-[[(tert-butyldiphenylsilyl)oxy]methyl]-3-methoxycyclopent-1-ene (17) with azidotrimethylsilane under Lewis acid catalyzed conditions gave an equilibrium mixture of allylic azides 18 and 19. Epoxidation of this mixture with peroxybenzimidic acid gave key epoxide (+/-)-(1alpha,2alpha,5alpha)-2-azido-2-[[tert-butyldiphenylsilyl)oxy]methyl]-6-oxabicyclo[3.1.0]hexane (5). Alternate routes designed to give tertiary azide precursors to 5 led to unanticipated products which are described. Title compound 28 was prepared by ring opening of 5 under Vorbruggen conditions followed by deprotection. Inversion of configuration at C-6' to give compound 30 was effected via O2,6'-cyclic intermediates 31 and 32. The relative stereochemistry of compounds in this series was suggested by NOE data for bromohydrins 23 and 26 and was confirmed by preparation of the fused oxetane 34.