(1R*,5S*)-5-methyl-8-oxabicyclo[3.2.1]octan-1-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1R*,5S*)-5-methyl-8-oxabicyclo[3.2.1]octan-1-ol
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: KHZKQZASYUVLPG-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1-氯-3-碘丙烷 、 乙酰丙酸乙酯 在 nickel(II) iodide 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以78%的产率得到(1R*,5S*)-5-methyl-8-oxabicyclo[3.2.1]octan-1-ol
  参考文献：
  名称：

  Sequenced Reactions with Samarium(II) Iodide. Sequential Intermolecular Carbonyl Addition/Intramolecular Nucleophilic Acyl Substitution for the Preparation of Seven-, Eight-, and Nine-Membered Carbocycles

  摘要：

  Samarium(II) iodide has been employed to promote a tandem intermolecular carbonyl addition/intramolecular nucleophilic acyl substitution sequence, generating seven- through nine-membered monocyclic, bicyclic, and tricyclic ring systems with good yields and high diastereoselectivities. This tandem reaction consists of an intermolecular reaction followed by an intramolecular ring expansion that results in a formal [m + n] cycloaddition, starting from extremely simple, readily available substrates. The regioselectivity and stereoselectivity of the process arise from a tuning of the reducing power of samarium(II) iodide with nickel(II) iodide in the first step and irradiation with visible light in the second. By using this method, a variety of structural motifs have been assembled rapidly in good yields.

  DOI：

  10.1021/jo980119e

文献信息

• Sequenced Reactions with Samarium(II) Iodide. Sequential Intermolecular Carbonyl Addition/Intramolecular Nucleophilic Acyl Substitution for the Preparation of Seven-, Eight-, and Nine-Membered Carbocycles
  作者：Gary A. Molander、Cristina Alonso-Alija

  DOI：10.1021/jo980119e

  日期：1998.6.1

  Samarium(II) iodide has been employed to promote a tandem intermolecular carbonyl addition/intramolecular nucleophilic acyl substitution sequence, generating seven- through nine-membered monocyclic, bicyclic, and tricyclic ring systems with good yields and high diastereoselectivities. This tandem reaction consists of an intermolecular reaction followed by an intramolecular ring expansion that results in a formal [m + n] cycloaddition, starting from extremely simple, readily available substrates. The regioselectivity and stereoselectivity of the process arise from a tuning of the reducing power of samarium(II) iodide with nickel(II) iodide in the first step and irradiation with visible light in the second. By using this method, a variety of structural motifs have been assembled rapidly in good yields.