1-Oxa-spiro[5.6]dodecan-2-one | 96517-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 1-Oxa-spiro[5.6]dodecan-2-one
• 英文别名: 1-Oxaspiro[5.6]dodecan-2-one
• CAS: 96517-21-4
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: FCGRTFSSINQACP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-Pent-4-enyl-cycloheptanol 在 chromium(VI) oxide 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 反应 4.0h， 以68%的产率得到1-Oxa-spiro[5.6]dodecan-2-one
  参考文献：
  名称：

  Substituent-directed oxidation: a simple preparation of γ and δ-lactones by oxidative cyclization of hydroxyalkenes.

  摘要：

  DOI：

  10.1016/s0040-4039(00)61860-9

文献信息

• Synthesis and Applications of Tetrahydrofuran-Stable Substituted (3-Lithioxyalkyl)- and (4-Lithioxyalkyl)lithiums, Modified with Magnesium 2-Ethoxyethoxide
  作者：Ioannis D. Kostas、Constantinos G. Screttas

  DOI：10.1021/jo9703010

  日期：1997.8.1

  Substituted hydroxyalkyl phenyl sulfides 3 have been synthesized from the corresponding allylic or homoallylic alcohols 2. Regiospecific cleavage of the C-SPh bond of the sulfides 3 by lithium dispersion in tetrahydrofuran (THF) led to the synthesis of substituted (3-lithioxyalkyl)- and (4-lithioxyalkyl)lithiums 4, most of which share the omega carbon with a carbocyclic ring. The organolithiums were modified with magnesium 2-ethoxyethoxide in order to suppress their reactivity toward THF cleavage, thus offering the advantage of preparing storable ethereal solutions of certain types of (lithioxyalkyl)lithiums. This strategy appears to be of rather broad scope. The functionalized organolithiums prepared in this way react normally with electrophilic reagents with yields in the range 35-55%. Thus, carboxylations of 4 yielded lactones 5, some of which are natural products, while reactions of 4 with benzophenone and cyclic ketones yielded 1,4- and 1,5-diols 6 and 7, respectively.
• Chow, Yuan L.; Huang, Yu-Jin; Dragojlovic, Veljko, Canadian Journal of Chemistry, 1995, vol. 73, # 5, p. 740 - 742
  作者：Chow, Yuan L.、Huang, Yu-Jin、Dragojlovic, Veljko

  DOI：——

  日期：——
• SCHLECHT, M. F.;KIM, HO-JIN, TETRAHEDRON LETT., 1985, 26, N 2, 127-130
  作者：SCHLECHT, M. F.、KIM, HO-JIN

  DOI：——

  日期：——
• Substituent-directed oxidation: a simple preparation of γ and δ-lactones by oxidative cyclization of hydroxyalkenes.
  作者：Matthew F. Schlecht、Ho-jin Kim

  DOI：10.1016/s0040-4039(00)61860-9

  日期：1985.1